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Bromdichlormethan

Bromodichloromethane

HCID 6359
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
75-27-4
Standard-SMILES
ClC(Cl)Br
InChIKey
FMWLUWPQPKEARP-UHFFFAOYSA-N
Summenformel
CHBrCl2
Durchschnittliche Molmasse
163,83 g/mol
Monoisotopische Masse
161,86387

Überblick

Bromodichloromethane is a colorless, nonflammable liquid. Small amounts are formed naturally by algae in the oceans. Some of it will dissolve in water, but it readily evaporates into air. Only small quantities of bromodichloromethane are produced in the United States. The small quantities that are produced are used in laboratories or to make other chemicals. However, most bromodichloromethane is formed as a by-product when chlorine is added to drinking water to kill bacteria.

Namen und Bezeichner

Bevorzugter Name
Bromodichloromethane
IUPAC
bromo(dichloro)methane
Lokaler Name
Bromdichlormethan
Englischer Name
BROMODICHLOROMETHANE
Summenformel
CHBrCl2
Molmasse
163.83

Namen und Synonyme

BROMODICHLOROMETHANE75-27-4DichlorobromomethaneMethane, bromodichloro-bromo(dichloro)methaneDichloromonobromomethaneMonobromodichloromethaneBDCMNCI-C55243DTXSID1020198Bromo-Dichloro-Methane7LN464CH2O
Weitere Namen anzeigen
DICHLOROIODOMETHANEBromdichlormethanFC-20B1BroModichloroMBromodichoromethaneBromodicloromethane
NSC-8018DTXCID30198CHEBI:34591NSC8018RefChem:121580200-856-7CHBrCl2NSC 8018

Datenbank-Bezeichner

CAS
75-27-4
PubChem CID
6359
DTXSID
DTXSID1020198
ChEMBL
CHEMBL346231
ChEBI
CHEBI:34591
UNII
7LN464CH2O
EC Number
200-856-7
Nikkaji

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,4
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
4
Formalladung
0
Komplexität
13,5

Experimentelle und physikochemische Eigenschaften

Chemical ClassesVolatile Organic Compound (VOC)
SolventsSolvents -> Brominated Solvents
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
LogP · 3 Einträge

log Kow = 2.00

2

2.1

Density · 5 Einträge

1.98 at 68 °F (NTP, 1992) - Denser than water; will sink

1.980 g/cu cm 20 °C

1.9 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.3

1.98 @ 20°C

Color/Form · 2 Einträge

Liquid

Colorless liquid

Solubility · 5 Einträge

5 to 10 mg/mL at 66 °F (NTP, 1992)

Very soluble in ethanol, ethyl ether, benzene and acetone; slightly soluble in carbon tetrachloride.

Very soluble in organic solvents; miscible with chloroform

In water, 3.968X10+3 mg/L at 30 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 3.3% (1 of 30) of reports.

Danger

H302 (96.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 30 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Gefahrenhinweise

Regulatory Information · 3 Einträge

Hazard Traits - Carcinogenicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity

Bromodichloromethane: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire Hazards · 2 Einträge

Literature sources indicate that this chemical is nonflammable. (NTP, 1992)

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialNONFLAMMABLE. WILL BURN ON PROLONGED EXPOSURE TO FLAME OR HIGH TEMPERATURE. /CHLOROFORM/
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and respiratory tract. It may also cause narcosis. Other symptoms may include nausea, dizziness and headache. It may also cause liver and kidney damage. Central nervous system effects may also occur. (NTP, 1992)

Chemie und Industrie

Pharmakologische Informationen

Biological Half-Life... A single oral dose of 20 mg/kg ... /as (14)C-bromodichloromethane/ in rats is cleared very rapidly. ... In monkeys ... the half-life of a similar dose was 4 to 6 hr...
Metabolism/Metabolites · 5 Einträge

... When administered to rodents, haloacetates have been shown to increase formation of thiobarbituric acid-reactive substances and 8-hydroxydeoxyguanosine levels in the liver. These responses appear to be modified by prior treatment. To examine potential mechanisms that account for these modifications in oxidative stress, the ability of trichloroacetate (TCA) or dichloroacetate (DCA) pretreatment to alter the metabolism of bromodichloroacetate (BDCA) and the disposition of its metabolites was examined in male B6C3F1 mice. Two-week pretreatment with 1 g/L DCA and TCA in the drinking water of mice alters the initial hepatic metabolism of BDCA and the further metabolism of its metabolite DCA. DCA pretreatment inhibits cytosolic metabolism of both 1 mM DCA or BDCA up to 70%. In contrast, DCA pretreatment stimulates hepatic microsomal BDCA metabolism 1.3-fold but has little effect on microsomal metabolism of DCA. Increased microsomal metabolism of BDCA appears to be attributable to the induction of a metabolic pathway that produces CO2 and bromodichloromethane (BDCM) as metabolites. TCA pretreatment inhibits BDCA metabolism up to 70% in the cytosol and 30% in microsomes but has little effect on DCA metabolism. These results indicate that the hepatic metabolism of the haloacetate becomes quite complex at the high doses that have been employed in cancer bioassays. BDCA serves as a good example, because it is metabolized to at least two carcinogenic metabolites that have different modes of action, BDCM and DCA. As doses approach those that induce cancer in mice, the proportion of and amounts of these metabolites as a fraction of the dose administered will change substantially. This article demonstrates that those interactions will occur from mixed treatment with haloacetates as well.

The drinking water disinfection byproduct bromodichloromethane (CHBrCl(2)) was previously shown to be mutagenic in Salmonella typhimurium that overexpress rat glutathione transferase theta 1-1 (GSTT1-1). Several experimental approaches were undertaken in this study to investigate the DNA covalent binding potential of reactive intermediates generated by GSTT1-1-mediated metabolism of CHBrCl(2). First, rodent hepatic cytosol incubations containing (14)CHBrCl(2), supplemented glutathione (GSH), and calf thymus DNA resulted in approximately 3-fold (rat liver cytosol) and 7-fold (mouse liver cytosol) greater amounts of total radioactivity (RAD) associated with the purified DNA as compared to a control (absence of rodent cytosol) following liquid scintillation counting (LSC) of isolated DNA. The relative increase in DNA labeling is consistent with the conjugation activity of these rodent cytosols toward CHBrCl(2). Second, exposure of GSTT1-1-expressing S. typhimurium to (14)CHBrCl(2) resulted in a concentration-dependent increase of bacterial DNA-associated total radioactivity. Characterization of DNA-associated radioactivity could not be assigned to a specific deoxynucleoside adduct(s) following enzymatic hydrolysis of DNA and subsequent HPLC analysis. A possible explanation for this observation was formation of a transient adduct that was unstable in the DNA isolation and hydrolysis procedures employed. To circumvent problems of adduct instability, reactions of (14)CHBrCl(2) with GSH catalyzed by recombinant rat GSTT1-1 were performed in the presence of calf thymus DNA or, alternatively, the model nucleophile deoxyguanosine. Hydroxyapatite chromatography of (14)C-labeled DNA or HPLC chromatography of (14)C-labeled deoxyguanosine derivatives demonstrated the covalent binding of (14)CHBrCl(2)-derived metabolites to DNA and deoxyguanosine in low yield (approximately 0.02% of (14)CHBrCl(2) biotransformed by GSTT1-1 resulted in DNA adducts). Cytochrome P450 (CYP)- and GST-catalyzed biotransformation of CHBrCl(2) in rat tissues (kidney and large intestine) that develop tumors following chronic CHBrCl(2) exposure were compared with rat liver (a nontarget tissue). Rat liver had a significant capacity to detoxify CHBrCl(2) (to carbon dioxide) compared with kidney and large intestine as a result of CYP-catalyzed oxidation, liver was approximately 16-fold more efficient than kidney and large intestine when intrinsic clearance values (V(max)/K(m)) were compared. In contrast, the efficiency of GST-mediated GSH conjugation of CHBrCl(2) in kidney and large intestine was only slightly lower than liver (approximately 2- to 4-fold lower), thus, the relative amounts of reactive intermediates that are produced with the capacity to covalently modify DNA may be enhanced in these extrahepatic tissues. The significance of these findings is that conjugation of CHBrCl(2) with GSH can result in the covalent modification of DNA and that cancer target tissues in rats have a much reduced detoxification capacity, but only a modest decrease in bioactivation capacity, as compared to the liver (a nontarget tissue in rats).

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J1.448F

Solubility in water, g/100ml at 20 °C: 0.45 (poor)

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 4 Einträge

189 °F at 760 mmHg (NTP, 1992)

90 °C

90 °C

88.5 °C @760 [mm Hg]

DecompositionWhen heated to decomp it emits very toxic fumes of /hydrogen bromide and hydrogen chloride/.
Melting Point · 4 Einträge

-67 °F (NTP, 1992)

-57 °C

-57 °C

-57.1 °C

Physikochemische Eigenschaften

Schmelzpunkt
55 °C · −55 °C(lit.)
Siedepunkt
87 °C · 87 °C(lit.)
Dichte
1.98 g/mL · 1.98 g/mL at 25 °C(lit.)
Dampfdruck
50 at · 50 at 20 °C (Dreisbach, 1952)
Brechungsindex
20 · n20/D 1.497(lit.)
Flammpunkt
87 · 87-89°C
storage temp.
2 · 2-8°C
Löslichkeit
water: insoluble
Aggregatzustand
liquid
Farbe
Clear, colorless liquid
Wasserlöslichkeit
3.032 g/L · 3.032g/L(30 ºC)
Spezifische Wärmekapazität
0.41 J/ · Cp(gas): 0.41 J/(g·K), at 25℃
Merck
14 · 14,1417
BRN
1697005 · 1697005
Henry's Law Constant
In seawater (salinity 30.4‰): 5.52, 10.51, and 18.97 at 0, 10, and 20 °C, respectively (Moore et al., 1995)
Stabilität
Light Sensitive, Volatile
Major Application
environmental
InChI
1S/CHBrCl2/c2-1(3)4/h1H
InChIKey
FMWLUWPQPKEARP-UHFFFAOYSA-N
SMILES
ClC(Cl)Br
CAS Datenbank
75 · 75-27-4(CAS DataBase Reference)
EPA chemische Informationen
Dichlorobromomethane (75-27-4)
Hazards Summary · 2 Einträge

Bromodichloromethane is a colorless, nonflammable liquid. Small amounts are formed naturally by algae in the oceans. Some of it will dissolve in water, but it readily evaporates into air. Only small quantities of bromodichloromethane are produced in the United States. The small quantities that are produced are used in laboratories or to make other chemicals. However, most bromodichloromethane is formed as a by-product when chlorine is added to drinking water to kill bacteria.

May cause skin, eye, mucous membrane, and respiratory tract irritation; May also cause narcosis and injury to liver and kidney; [CAMEO] May cause liver and kidney injury; [ICSC]

Reactive GroupHalogenated Organic Compounds
Special Reports · 4 Einträge

USEPA; Ambient Water Quality Criteria Doc: Halomethanes (1980) EPA 440/5-80-051. This document reviews the following halomethanes: chloromethane, bromomethane, methylene chloride, bromoform, bromodichloromethane, trichlorofluoromethane, and dichlorodifluoromethane.

DHHS/ATSDR; Toxicological Profile for Bromodichloromethane (1989) ATSDR/TP-89/04

DHHS/NTP; Toxicology & Carcinogenesis Studies of Bromodichloromethane in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 321 (1987) NIH Publication No. 88-2537

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Bromodichloromethane (75-27-4) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s023brom.pdf]

TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Bromodichloromethane is included on this list. Effective date 6/1/87; Sunset date: 12/19/95.

Reactivity ProfileDICHLOROBROMOMETHANE may react with strong bases and magnesium. Incompatible with oxidizing materials (NTP, 1992).
Chemical DangersDecomposes on contact with hot surfaces or flames. This produces toxic and corrosive gases including hydrogen bromide and hydrogen chloride. Reacts with strong bases, strong oxidants and magnesium.
Physical DangersThe vapour is heavier than air.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong oxidants, strong bases and magnesium. Ventilation along the floor.
Storage ConditionsSTORE IN COOL, DRY, WELL-VENTILATED LOCATION. SEPARATE FROM STRONG ALKALIS & STRONG MINERAL ACIDS. /CHLOROFORM/
Cleanup Methods · 4 Einträge

1. VENTILATE AREA OF SPILL OR LEAK. 2. COLLECT FOR RECLAMATION OR ABSORB IN VERMICULITE, DRY SAND, EARTH, OR A SIMILAR MATERIAL. /CHLOROFORM/

Do not touch spilled material. Use water spray to reduce vapors. For small spills, take up with absorbent material then flush area with water. For large spills, dike far ahead. /Chloroform/

/SRP: In laboratory setting only:/ Absorb on paper and evaporate on a glass dish in hood. Burn the paper. Purify /liquids/ by distillation, then return to supplier. /Chloroform/

Oxidation processes are responsible for the removal of organic compounds and precursors of trihalomethanes. Substitution reactions are the source of chlorine incorporation into the organic matter. Disinfectants differ in their abilities to carry out oxidation and substitution reactions, but studies show that chloramines also add chlorine to organic materials by substitution. Before a decision is made to change disinfectants, operating parameters and chemical functions must be taken into account to achieve the best quality drinking water.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 5 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Chloroform is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration, preferably after mixing with another combustible fuel; care must be exercised to assure complete combustion to prevent the formation of phosgene; an acid scrubber is necessary to remove the halo acids produced. /Chloroform/

Potential candidate for liquid injection incineration, with a temperature range of 650 to 1600 °C and a residence time of 0.1 to 2 seconds; for rotary kiln incineration with a temperature of 820 to 1600 °C and a residence time of seconds for liquids and gases, hours for solids; and for fluidized bed incineration, with a temperature range of 450 to 980 °C and a residence time of seconds for liquids and gases, longer for solids. /Chloroform/

The following wastewater treatment technologies have been investigated for bromodichloromethane. Concentration process: stripping.

For more Disposal Methods (Complete) data for BROMODICHLOROMETHANE (7 total), please visit the HSDB record page.

Preventive Measures · 5 Einträge

Skin that becomes wet with liquid chloroform should be promptly washed or showered with soap or mild detergent and water to remove any chloroform. Employees who handle chloroform should wash their hands thoroughly with soap and mild detergent and water before eating or smoking. /Chloroform/

Where there is any possibility that employees' eyes may be exposed to chloroform, an eye-wash fountain should be provided within the immediate work area for emergency use. /Chloroform/

Good industrial hygiene practices recommend that engineering controls be used to reduce environmental concentrations to the permissible level. However, there are some exceptions where respirators may be used to control exposure. Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed, or when they fail and need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. In addition to respirator selection, a complete respiratory protection program should be instituted which includes regular training, maintenance, inspection, cleaning, and evaluation. /Chloroform/

Clothing wet with liquid chloroform should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of chloroform from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the chloroform, the person preforming the operation should be informed of chloroform's hazardous properties. /Chloroform/

For more Preventive Measures (Complete) data for BROMODICHLOROMETHANE (6 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear safety spectacles.
Inhalation RiskA harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

Toxikologische Informationen

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1 Eintrag

A bromodichloromethane concn of 14 ng/mL was found in a blood sample from a resident living near the Love Canal near Niagara Falls, NY(1). Bromodichloromethane was not detected in any sample from the USEPA National Human Adipose Tissue Survey for fiscal year 1982(2,5). Bromodichloromethane was detected in 14% of the 1072 blood samples (detection limit 0.009 ppb) from a nonoccupationally exposed US population from a survey run from 1988 to 1994(3). Alveolar breath samples of competitive swimmers during a typical 2-hr training period in an indoor facility contained an average of 2.68 ug/cu m bromodichloromethane(4). The estimated blood/breath coefficient was estimated at 0.01 and 0.12 ug/L for the male and female subjects, respectively (detection limit = 0.39 ug/cu m)(4). Alveolar air samples taken in swimmers in Modena, Italy found bromodichloromethane in 30 of 32 at a mean concn of 1.8 ug/cu m(5). Bromodichloromethane was identified in one of eight samples of mother's milk collected from nursing mother's in New Jersey hospitals(6). Bromodichloromethane was found in alveolar air of swimmers at rates of 2.7 ug/cm before swimming to 6.5 ug/cm after swimming. Uptake rates were calculated in the range of 3 ug/hour before swimming and 26 ug/hour after swimming based on research of five swimmers(7). Bromodichloromethane was found in the blood of bath attendants at <0.6 ug/L and in swimmers at <1.8 ug/L(8). Bromodichloromethane was found in blood of women in Cobb County, Georgia at levels of 0.002-0.017 ug/L before showering and 0.017-0.093 ug/L after showering(9). Bromodichloromethane was also found in blood of women from Corpus Christi, Texas at before shower levels of 0.002-0.035 ug/L and after shower levels from 0.009-0.083 ug/L(9).

Cancer SitesUrinary
Interactions · 5 Einträge

... The effects of glutathione (GSH) on in vivo bromodichloromethane (BDCM)toxicity and in vitro BDCM macromolecular binding were evaluated. The in vivo toxicity of BDCM in animals pretreated with buthionine sulfoximine (BSO, a glutathione synthesis inhibitor) and in untreated male Fischer 344 rats was investigated. In another experiment, covalent binding to protein and lipid was quantified after (14C)BDCM was incubated with hepatic microsomal and S9 fractions and renal microsomes from F344 rats, under aerobic and anaerobic conditions, with and without added GSH. After oral dosing with BDCM, the BSO-pretreated animals had greatly increased levels of serum indicators of hepatotoxicity and serum and urinary indicators of nephrotoxicity compared to those in animals dosed solely with BDCM. Histopathological examination revealed that hepatic necrosis was more severe than renal necrosis in the BSO-treated rats. When GSH was added to an aerobic incubation, protein binding was decreased in hepatic microsomal and S9 fractions by 92 and 83%, respectively. GSH also decreased lipid binding by 55% in hepatic microsomal incubations carried out under anaerobic conditions. Addition of GSH decreased renal microsomal protein (aerobic) and lipid binding (anaerobic) by 20 and 43%, respectively. These data indicate that GSH is an important protective factor in the toxicity associated with BDCM.

The acute hepato- and nephrotoxic potentials of two trihalomethane water contaminants, bromodichloromethane (BrCHCl2) and dibromochloromethane (Br2CHCl), were determined in male Sprague-Dawley rats. Br2CHCl possessed a greater hepatotoxic and lethal potential than BrCHCl2. However, both Br2CHCl and BrCHCl2 were weak hepatotoxicants as compared to a related trihalomethane, CHCl3. Br2CHCl and BrCHCl2 did not produce liver injury until near-lethal dosages were administered. Neither trihalomethane appeared to produce appreciable kidney injury during the 24-hr challenge period. Pretreatment of rats with acetone (15 mmol/kg, po) markedly potentiated the hepatotoxic response to BrCHCl2 and Br2CHCl. The potentiated response observed with acetone plus BrCHCl2 or Br2CHCl was equal to or greater than that observed with acetone plus an approximately equimolar dosage of CHCl3. That is, acetone appeared to convert these weak hepatotoxicants into strong hepatotoxicants.

... A rodent model of hereditary renal cancer was used to investigate the carcinogenic response to a mixture of drinking water disinfection by-products (DBPs). Rats carrying a mutation in the Tsc2 tumor suppressor gene (Eker rats) readily develop renal preneoplastic and neoplastic lesions, and are highly susceptible to the effects of renal carcinogens. Male and female Eker rats were exposed via drinking water to individual or a mixture of DBPs for 4 or 10 months. Potassium bromate, 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), chloroform, and bromodichloromethane were administered at low concentrations of 0.02, 0.005, 0.4 and 0.07 g/L, respectively, and high concentrations of 0.4, 0.07, 1.8 and 0.7 g/L, respectively. Low and high dose mixture solutions were comprised of all four chemicals at either low concentrations or high concentrations, respectively, Following necropsy, each kidney was examined microscopically for preneoplastic lesions (atypical tubules and hyperplasias) and tumors. While some of the mixture responses observed in male rats did fall within the range expected for an additive response, especially at the high dose, predominantly antagonistic effects on renal lesions were observed in response to the low dose mixture in male rats and the high dose mixture in female rats. These data suggest that current default risk assessments assuming additivity may overstate the cancer risk associated with exposure to mixtures of DBPs at low concentrations..

Pretreatment of Fischer 344 rats with buthionine sulfoximine, which decreased the hepatic glutathione content by 86%, markedly accentuated the hepatic and renal toxicity of bromodichloromethane administered as a single dose (400 mg/kg bw) by gavage.

For more Interactions (Complete) data for BROMODICHLOROMETHANE (6 total), please visit the HSDB record page.

Target Organs · 2 Einträge

Cancer, Developmental (effects while organs are developing), Hepatic (Liver), Immunological (Immune System), Renal (Urinary System or Kidneys)

Urinary

Ecotoxicity ValuesEC50; Species: Tetrahymena pyriformis (Ciliate); Conditions: static, 30 °C; Concentration: 240000 ug/L for 24 hr; Effect: growth, general
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), estimated Koc values of 53-251(2-4), indicate that bromodichloromethane is expected to have high to moderate mobility in soil(SRC). Volatilization of bromodichloromethane from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.12X10-3 atm-cu m/mole(5). Bromodichloromethane is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 50 mm Hg(6). No degradation occurred in 6 weeks using mixed methanogenic bacterial cultures from sewage effluents in either sterile or seeded conditions(7), suggesting that biodegradation may not be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), estimated Koc values of 53-251(2-4), indicate that bromodichloromethane is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(5) based upon a Henry's Law constant of 2.12X10-3 atm-cu m/mole(6). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 4 hours and 5 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 7(SRC), from an estimated log Kow of 2.00(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 186 and 18.6 years at pHs 7 and 8, respectively(9). No degradation occurred in 6 weeks using mixed methanogenic bacterial cultures from sewage effluents in either sterile or seeded conditions(10), suggesting that biodegradation may not be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromodichloromethane, which has a vapor pressure of 50 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase bromodichloromethane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 205 days(SRC), calculated from its rate constant of 7.8X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Bromodichloromethane does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). The detection of bromodichloromethane in rainwater(5) indicates that atmospheric removal via washout can occur; however, any bromodichloromethane which is removed by rainfall is likely to revolatilize into the atmosphere(SRC).

Food Survey Values · 1 Eintrag

In accordance with the USFDA's Total Diet Market Basket Study, an analysis of 39 food items purchased at retail markets (from Elizabeth, NJ, Chapel Hill, NC, Washington, DC) detected bromodichloromethane in one dairy composite (1.2 ppb), in butter (7 ppb), and in two beverages (0.3 and 0.6 ppb); subsequent analysis of cola soft drinks resulted in three positive detections at levels of 2.3, 3.4, and 3.8 ppb(1). An analysis of various soft drinks found cola beverages to ave 0.9-5.9 ppb bromodichloromethane while clear soft drinks had levels of 0.1-0.2 ppb; municipal water supplies from which the soft drinks were manufactured were found to contain up to 20 ppb trihalomethanes(2). Bromodichloromethane was found in the following foods: flavored sparkling water, 12 ng/g; fruit drink, 5 ng/g; carbonated soft drinks, 1-12 ng/g(3). The compound was not detected (detection limit= 12 ppb) in butter purchased from retail outlets located near dry-cleaning establishments(4). Bromodichloromethane was found in grapefruit juice (0.20 ug/kg); reconstituted lemon juice (1.05 ug/kg); reconstituted lime juice (1.00 ug/kg); reconstituted orange juice (0.20-1.27 ug/kg); and in orange drink (0.80 ug/kg)(5). The following foods were also found to contain bromodichloromethane: whey and longhorn cheese process water (2.2 ng/g); gingerale soda (2.3 ng/g); sparkling soda (1.2 ng/g); cola soda (1.2 ng/g); ricotta and mozzarella cheese process waters (3.0-8.3 ng/g); process water for lemon-lime soda, lemon soda, and cola soda - trace; process water for vanilla, chocolate, and butter-pecan ice creams (8.3-14.1 ng/g); vanilla ice cream (2.3 ng/g); chocolate ice cream (0.6 ng/g); and butter pecan ice cream (1.1 ng/g)(6). Bromodichloromethane was detected at <0.1-5.2 ppm in bean-curd and water in packaging(7). Summer and winter food intake for 30 Japanese housewives contained concns of bromodichloromethane of not detected to 1.7 ng/g and not detected to 0.8 ng/g in Nagoya, and winter food intake for 30 housewives from Yokohama contained bromodichloromethane from not detected to 1.2 ng/g(8).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by ingestion.
Milk ConcentrationsEXPERIMENTAL: Bromodichloromethane was detected in whole milk, 2% milk, and 1% milk at 0.02-0.30, 0.03-0.37, and 0.04-0.14 ng/mL in 35 samples taken from 8 grocery stores, Jan and Feb 2002 in Las Vegas, NV(1).
Average Daily Intake · 1 Eintrag

AIR INTAKE: The estimated daily air intake of bromodichloromethane in a study involving 17 subjects from Beaumont, TX and Chapel Hill, NC ranged from below the detection limit (<1.2 ug/10 cu m) for 9 subjects to 37.1 ug/10 cu m(1); DRINKING WATER INTAKE: Water intake ranged from 15 to 24 ug/L, assuming 10 cu m/d respiration rate and 1 L/d ingestion rate. The percentage intake from air ranged from <3 to 73. This did not take into account exposure from showering which presumably would increase the proportion due to inhalation(1).; FOOD INTAKE: The average daily intake of bromodichloromethane for 30 Japanese housewives was 0.2-2.3 ug and 0.1-1.1 ug in summer and winter in Nagoya and 0.2-1.8 ng for 30 housewives in Yokohama(2).

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Bromodichloromethane is included on this list. Effective date 6/1/87; Sunset date: 12/19/95.

CERCLA Reportable Quantities · 1 Eintrag

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Halomethanes/
State Drinking Water Guidelines · 5 Einträge

(AZ) ARIZONA 0.19 ug/L

(MN) MINNESOTA 6 ug/L

(NH) NEW HAMPSHIRE 0.60 ug/L

(WI) WISCONSIN 0.6 ug/L

(ME) MAINE 6 ug/L

Federal Drinking Water StandardsEPA 80 ug/L

Sicherheitsdaten

F
8
wgk
3
tsca
TSCA listed
ridadr
2810
hs_code
29037990
RTECS-Nr.
PA5310000
risk_code
22-37/38-40-41-39/23/24/25-23/24/25-11
Toxizität
LD50 in male, female mice (mg/kg): 450, 900 orally (Bowman)
hazard_code
Xn,T,F
safety_code
26-36/39-45-36/37-16-36/37/39-36-7
hazard_class
6.1
packing_group
III
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
75-27-4(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralCarc. 2Eye Dam. 1Skin Irrit. 2STOT SE 3

Haloforms are metabolized to carbon monoxide by hepatic mixed function oxidases & this reaction is markedly stimulated by sulfhydryl cmpd. Max stimulation occurred at 0.5 mmolar glutathione. A mechanism for conversion of haloforms to carbon monoxide is proposed. /Haloforms/

Trihalomethanes (haloforms) were metabolized to carbon monoxide by a rat liver microsomal fraction requiring NADPH & molecular oxygen for max activity. Results suggest haloforms are metab to carbon monoxide by a cytochrome P450 dependent mixed-function oxidase system. /Trihalomethanes/

For more Metabolism/Metabolites (Complete) data for BROMODICHLOROMETHANE (9 total), please visit the HSDB record page.

MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Absorption, Distribution and Excretion · 5 Einträge

A single oral dose of 20 mg/kg ... /as (14)C-bromodichloromethane/ in rats is cleared very rapidly. Only 32% is recovered from GI tract & carcass after 3 hr, & 41% after 6 hr. Most of cmpd was recovered from stomach. Fat contained more than any other tissue. Less than 1% appeared in urine. Balance ... probably exhaled ...

A 31-day rat-dosing sequence was used to study some aspects of physiological distribution, metabolism, storage & rate of elimination of bromodichloromethane from rat adipose & blood serum. For the volatile cmpd, tissue levels fluctuated but did not indicate incr storage with time. Adipose tissue to blood serum levels never differed by more than a factor of 3. Within 3-6 days after dosing was terminated, most of the halogenated cmpd had left the examined tissues.

Bromodichloromethane may be absorbed readily by inhalation or ingestion, be distributed widely, preferentially to tissues with high lipid content, and be eliminated in part via expired breath.

Pharmacokinetics and tissue distribution of bromodichloromethane was examined in rats and monkeys. The compound was excreted primarily via the lung either unchanged or as metabolites.

For more Absorption, Distribution and Excretion (Complete) data for BROMODICHLOROMETHANE (13 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 4 Einträge

Used as chemical reagent/intermediate in organic synthesis; Also used as a fire extinguisher, solvent (fats, waxes, and resins), and as a heavy liquid for mineral and salt separations; [HSDB]

Chemical reagent, intermediate in organic synthesis.

Organic synthesis, solvent

Fire extinguisher fluid ingredient; solvent (fats, waxes, resins); synthesis intermediate; heavy liquid for mineral and salt separations.

U.S. Production · 2 Einträge

(1977) NOT PRODUCED COMMERCIALLY IN USA

(1979) NOT PRODUCED COMMERCIALLY IN USA

Methods of Manufacturing · 1 Eintrag

Treatment of the chlorine analog with slightly more than the stoichiometric quantity of anhydrous aluminum bromide, or with hydrogen bromide in the presence of an aluminum halide catalyst. After replacement of chlorine by bromine, the mixture is washed with cold water to remove the inorganic materials and the product is distilled.

Formulations/Preparations98+% grade
Use ClassificationChemical Classes -> Volatile organic compounds
General Manufacturing Information · 2 Einträge

Methane, bromodichloro-: ACTIVE

Bromodichloromethane is not manufactured for commercial use, but is formed in chlorinated drinking water as a result of the halogen substitution and oxidation reactions of chlorine with naturally occurring organic matter (e.g., humic or fulvic acids) in the presence of bromide.

Anwendungen · 1 Eintrag

VerwendenAs a chemical intermediate for organic synthesis and as a laboratory reagent; formerly used as a solvent and flame retardant. Currently, the major source of bromodichloromethane in the environment is from its formation as a by-product during chlorination of water.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

DL-Methionin-S-dioxidCyclopropan1,1-DichloracetonCHLORIDE STANDARDDibromchlormethanTrichlormethan

Nachgelagerte Produkte

2,6-Piperidinedione, 3,3-dimethyl-5-Methylthiophen-2-carbaldehyd3-METHYL-1H-INDOLE-2-CARBALDEHYDE

Ergänzende Hinweise

DefinitionChEBI: A one-carbon compound that is methane substituted by a bromo and two chloro groups. It occurs as a contaminant in drinking water.