Pentachlorobenzene

HCID 11855CAS 608-93-5

Grundinformationen

Standard-SMILES
Clc1cc(Cl)c(Cl)c(Cl)c1Cl
InChIKey
CEOCDNVZRAIOQZ-UHFFFAOYSA-N
Summenformel
C6HCl5
Durchschnittliche Molmasse
250,3 g/mol
Monoisotopische Masse
247,85208843

Überblick

Pentachlorobenzene appears as white crystals. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Pentachlorobenzene
IUPAC
1,2,3,4,5-pentachlorobenzene
Englischer Name
Pentachlorobenzene
Summenformel
C6HCl5
Molmasse
0

Namen und Synonyme

PENTACHLOROBENZENE608-93-51,2,3,4,5-PentachlorobenzeneBenzene, pentachloro-DTXSID7024247D62GWO6832NSC-1857Benzene, 1,2,3,4,5-pentachloro-DTXCID804247CHEBI:47136RefChem:171303210-172-0
Weitere Namen anzeigen
RCRA waste number U183QCBCCRIS 5927HSDB 2863C6HCl5NSC 1857EINECS 210-172-0RCRA waste no. U183

Datenbank-Bezeichner

CAS
608-93-5
PubChem CID
11855
DTXSID
DTXSID7024247
ChEMBL
CHEMBL44628
ChEBI
CHEBI:47136
UNII
D62GWO6832
EC Number
210-172-0
Nikkaji
J2.078H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,2
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Halogenated Monoaromatics
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Pesticides · 2 Einträge

Pesticide -> EPA IRIS

Pesticide (Pentachlorobenzene (PCB)) -> USDA PDB

LogP · 3 Einträge

log Kow = 5.18

5.03/5.63

5.2

OdorPleasant aroma
Density · 5 Einträge

1.8342 (NTP, 1992) - Denser than water; will sink

1.8342 at 16.5 °C

Liquid density: 1.609 g/cu cm at 84 °C

Relative density (water = 1): 1.8

1.8342 @ 16°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H228: Flammable solid [Danger Flammable solids]

P210, P240, P241, P264, P270, P273, P280, P301+P317, P330, P370+P378, P391, and P501 (click each P-code to see the statement)

Danger

H228 (100%): Flammable solid [Danger Flammable solids]

P210, P240, P241, P264, P270, P273, P280, P301+P317, P330, P370+P378, P391, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

Hazard Traits - Bioaccumulation; Environmental Persistence; Environmental tox

S - indicates a substance that is identified in a final Significant New Use Rule.

Substance: Pentachlorobenzene

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.)

Other Safety InformationEvaluation - Benzene, 1,2,3,4,5-pentachloro- (PeCB)
DOT LabelClass 9
Fire Hazards · 2 Einträge

Flash point data for this compound are not available but it is probably non-flammable. (NTP, 1992)

Combustible under specific conditions. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialNot flammable or combustible.
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

A fire in your laboratory involving this chemical should be extinguished with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest.

Remove contaminated clothes. 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. Refer for medical attention .

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 StorageProvision to contain effluent from fire extinguishing.
Fire Fighting Procedures · 3 Einträge

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray, powder, foam, carbon dioxide.

Use water spray to cool unopened containers.

Storage Conditions · 2 Einträge

Keep container tightly closed in a dry and well-ventilated place.

Provision to contain effluent from fire extinguishing.

Toxikologische Informationen

Body Burden · 3 Einträge

Pentachlorobenzene concentrations were reported as follows: Slovenia Province, Yugoslavia: human adipose tissue, 1979-80, 15 samples, not detected to 3 ppb, 1.2 ppb average (fat basis), human milk, 1981, 12 samples, 18 ppb (fat basis)(1); human milk, 6 samples, 0-3.4 ppb, 2.0 ppb average, 2 whole milk(2). In an analysis of human adipose autopsy samples from six municipalities in Ontario, Canada, pentachlorobenzene was qualitatively detected (1.9 ppb detection limit) as follows(3): Cornwall, 4% of 21 patients; London, 3% of 37 patients; St. Catherines, 12% of 17 patients; Windsor, 14% of 36 patients; Toronto, 0% of 7 patients; Welland, 0% of 7 patients(3). Pentachlorobenzene was not detected in the tissue of 7 patients from Toronto or 23 patients from Welland(4).

Pentachlorobenzene /was found/ at /a concentration of/ 0.009 ppm in samples of human adipose tissue in Japan.

A survey of human milk from the general and indigenous (Canadian Indian and Inuit mothers) population of Canada found pentachlorobenzene residues in 17% of the 18 indigenous population samples at an avg concn of positive samples of 2 ppb (milkfat basis) and trace levels (whole milk basis) and in 97% of the general population samples (number of samples not reported) at an average concentration of positive samples of 3 ppb (milkfat basis) and 0.1 ppb (whole milk basis)(1).

Target OrgansHepatic
Ecotoxicity Values · 5 Einträge

LC50; Species: /Lepomis macrochirus/ (Bluegill sunfish); Concentration: 2.27 mg/L for 24 hr; 0.55 mg/L for 48 hr; 0.25 mg/L for 96 hr /Conditions of bioassay not specified/

LC50; Species: /Cyprinidon variegatus/ (Sheepshead minnow); Concentration: >32.0 mg/L for 24 hr; 9.55 mg/L for 48 hr; 0.83 mg/L for 96 hr /Conditions of bioassay not specified/

LC50; Species: Poecilia reticulata (guppy); Concentration: 0.178 ppm for 14 days /Conditions of bioassay not specified/

EC50; Species: Pseudokirchneriella subcapitata (Green Algae); Conditions: freshwater, static; Concentration: 32000 ug/L for 24 hr; Effect: population, chlorophyll A concentration /formulation/

For more Ecotoxicity Values (Complete) data for PENTACHLOROBENZENE (9 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an experimentally-derived Koc range of 3162 to 5.24X10+6(2-4), indicates that pentachlorobenzene is expected to have slight to no mobility in soil(SRC). Volatilization of pentachlorobenzene from moist soil surfaces may be an important fate process(SRC) given a Henry's Law constant of 7.03X10-4 atm-cu m/mole at 25 °C(5), however, strong adsorption to soil will attenuate the importance of volatilization(SRC). Pentachlorobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.002 mm Hg at 25 °C(6). Pentachlorobenzene was shown to be resistant to degradation in laboratory soil tests with half-lives of 194 and 345 days reported in duplicate experiments(7). Pentachlorobenzene is resistant to biodegradation under aerobic conditions(8). Anaerobic biodegradation in soil and sediments yields lower chlorinated benzenes, but the rate can be highly variable(8). Higher organic matter contents seem to drastically increase the persistency(8); the true field half life of pentachlorobenzene is estimated around 6 years in organic soil and sediment in the temperate zone(8).

AQUATIC FATE: Based on a classification scheme(1), an experimentally-derived Koc range of 3162 to 5.24X10+6(2-4), indicates that pentachlorobenzene 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 7.03X10-4 atm-cu m/mole(6), but adsorption may attenuate this process(SRC). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 6.6 hours and 6.9 days, respectively, when adsorption is ignored(SRC). The volatilization half-life from a model pond is about 11 months when adsorption is considered(7,SRC). According to a lassification scheme(8), a BCF range 1085 to 20,000(9), suggests that bioconcentration in aquatic organisms is very high(SRC). Pentachlorobenzene may be susceptible to direct photolysis from surface water. When irradiated with light >290 nm in water, it resulted in 41% photodegradation after 24 hrs(10). Pentachlorobenzene is resistant to biodegradation in sediments under aerobic conditions(9). In anaerobic sediment-water slurries pentachlorobenzene is considered persistent, with a possible exception at temperatures above 10 °C in combination with low organic matter contents(9). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pentachlorobenzene, which has a vapor pressure of 0.002 mm Hg at 25 °C(2), is expected to exist almost entirely in the vapor phase in the ambient atmosphere. Vapor-phase pentachlorobenzene 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 about 277 days(SRC) from its estimated rate constant of 5.8X10-14 cu cm/mole-sec(3). Pentachlorobenzene absorbs UV light >290 nm(4), therefore, pentachlorobenzene may be susceptible to direct photolysis by sunlight(SRC). Although pentachlorobenzene is expected to exist primarily in the vapor-phase in the atmosphere, it has been detected in atmospheric dust that settles to the ground via dry deposition(5). Pentachlorobenzene has also been measured in rain and snow precipitation samples(6) which indicates it can be removed from air via wet deposition(SRC). Monitoring data indicate that pentachlorobenzene is subject to long range transport(6).

Food Survey Values · 4 Einträge

Pentachlorobenzene was detected in 20 of 1,500 composite foods in the US with a daily intake of 0.3 ug in 1975 and in 12 of 1,500 composite food samples in the US with a daily intake of 0.03 ug in 1976(1). In 1976-1977 pentachlorobenzene was detected in 15 of 300 composite food samples in the US at trace concentrations to 0.003 ppm(2) and in 1977-1978 was detected in 22 of 240 composite food samples at concentrations of trace amounts to 0.005 ppm(3). Pentachlorobenzene was detected in 3 of 117 infant food samples at concentrations of trace amounts to 0.005 ppm and in 10 of 132 toddler food composites at concentrations of trace amounts to 0.010 ppm(4). Pentachlorobenzene was detected in 4 of 98 infant food samples at concentrations of 0.002-0.012 ppm and in 13 of 110 toddler food composites at concentrations of trace amounts to 0.008 ppm(5). Pentachlorobenzene has been found in the following crude seed oils: Yugoslavian corn oil (0.010 ppm), rape seed oil (0.001 ppm), sunflower oil (0.005 ppm), walnut oil (0.005 ppm), and poppy oil (0.005 ppm); US soybean oil (trace concentration); Chinese peanut oil (0.005 ppm) and sesame seed oil (trace concentration); Turkish hazelnut oil (0.001 ppm)(6).

Pentachlorobenzene was detected in 2 percent of all food products sampled in the US between 1982-1984 and 1 percent of food products sampled between 1984-1986(1). Pentachlorobenzene was detected in 15 of 230 ready to eat foods in the US at an average concentration of 0.0012 ug/g(2).

Pentachlorobenzene was detected in 15 of 20 composite samples of fats and oils at a range of trace levels to 0.003 ppm(1), 1 of 20 composite samples of meat, fish and poultry at trace levels, 1 of 20 composite samples of grain and cereal at a concn of 0.002 ppm and in 1 of 20 composite samples of potatoes at 0.008 ppm obtained from 20 US cities(1). Pentachlorobenzene was detected in 9 of 20 composite samples of fats and oils at a concentration range of trace levels to 0.019 ppm and in 2 of 20 composite samples of sugars and sugar adjuncts at trace levels and 0.001 ppm in 20 US cities(2). Pentachlorobenzene was detected in 21 of 27 composite samples of fats and oils at a range of trace levels to 0.004 ppm, in 1 of 27 composite samples of root vegetables at trace levels and in 2 of 27 composite samples of sugars and sugar adjuncts at trace levels collected in 27 US cities(3).

... in peanut butter samples: avg: 16 ppb, range: 1.8-62 ppb ...

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

U183; As stipulated in 40 CFR 261.33, when pentachlorobenzene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

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. Pentachlorobenzene is included on this list. Effective date: 10/4/82; Sunset date: 10/4/92.

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 10 lb or 4.54 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. /Chlorinated benzenes/
State Drinking Water Guidelines · 2 Einträge

(AZ) ARIZONA 6 ug/l

(FL) FLORIDA 5.6 ug/l

Sicherheitsdaten

Alarmwort
Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H228

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 6 Einträge

The biliary excretion of metabolites of hexachlorobenzene was studied in rats dosed intragastrically with (14)c-hexachlorobenzene. By GLC-mass spectrometry, 1.8% of the (14)C excreted in the 24 hour bile was shown to be due to pentachlorobenzene.

Pentachlorobenzene is a metabolite of hexachlorobenzene in chick embryo liver cell primary culture.

Pentachlorobenzene yields chlorobenzene in rabbit. From table/

When pentachlorobenzene was added to culture of mold, degradation produced following metabolites: pentachlorophenol, 2,3,4,5- & 2,3,4,6-tetrachlorophenol; 1,2,3,4-tetrachlorobenzene; 1,2,4,5- &/or 1,2,3,5-tetrachlorobenzene; 2,3,4-, 2,4,6- & 3,4,5-trichlorophenol; & 1,3,5-trichlorobenzene.

For more Metabolism/Metabolites (Complete) data for PENTACHLOROBENZENE (8 total), please visit the HSDB record page.

Pentachlorobenzene has known human metabolites that include Pentachlorophenol.

MeSH Pharmacological Classification · 2 Einträge

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

Absorption, Distribution and Excretion · 5 Einträge

... Pentachlorobenzene ... accumulated to appreciable extent in both maternal & fetal tissues /after daily oral administration of 50, 100 & 200 mg/kg to rats on days 6-15 of gestation or 22-day-old fetuses/.

The mean levels of chlorobenzenes (including pentachlorobenzene) in human milk and adipose tissue were determined and ranged from traces to 25 ug/kg for human milk and from not detected to 146 ug/kg for adipose tissue. The distribution of different chlorobenzene isomers in adipose tissue and milk was different.

Single oral doses of 0.5 mg/kg of (14)c-pentachlorobenzene were given to male and female rhesus monkeys. The chemical was readily absorbed and evidence indicates that the lymphatic system was involved in the absorption process. The major excretory pathway was via the feces. It is suggested that the metabolic system involved some mechanism other than the hepatic cytochrome p450. It is suggested that two different hydroxylation pathways could be involved. The first calls for oxidation of the pentachlorobenzene to pentachlorophenol, aND the 2ND calls for nucleophilic displacement reactions of pentachlorobenzene to tetrachlorophenols in sites which are metabolically active, other than the liver.

The reported data are part of a continuing monitoring program of chlorinated hydrocarbons in adipose tissue of canadians in order to monitor disappearance of restricted organochlorine pesticides as well as the appearance of new environmental contaminants. Human adipose tissues were obtained during autopsies on accident victims. Pentachlorobenzene was found in all tissues sampled, regardless of geographic region, age, or sex of the subject. Amounts recovered were erratic, however, making quantitative determinations invalid.

For more Absorption, Distribution and Excretion (Complete) data for PENTACHLOROBENZENE (8 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 4 Einträge

Used as a chemical intermediate for pentachloronitrobenzene; [HSDB]

Chemical intermediate for pentachloronitrobenzene

Pentachlorobenzene is not known to have any commercial uses at present. In the past, pentachlorobenzene was one component of a chlorobenzenes mixture used to reduce the viscosity of PCB /polychlorinated biphenyl/ products employed for heat transfer. Pentachlorobenzene has also been used in a chlorobenzenes mixture with PCBs in electrical equipment. Pentachlorobenzene was used in the past as an intermediate in manufacture of pentachloronitrobenzene (quintozene), however, quintozene is now made by chlorination of nitrobenzene. Pentachlorobenzene may also have been used in the past as a fungicide and flame retardant.

Formerly used as a dye carrier

U.S. Production(1977) AT LEAST 4.54X10+8 G
Consumption PatternsESSENTIALLY 100% AS A CHEM INT FOR PENTACHLORONITROBENZENE
Methods of Manufacturing · 2 Einträge

Chlorination of benzene gives a mixture of tetra-, penta-, and hexachlorobenzenes, from which pentachlorobenzene can be isolated by combined distillation and crystallization steps.

When BHC /benzene hexachloride/ is chlorinated in carbon tetrachloride, various substitution derivatives are formed. By use of liquid chlorine, higher substituted derivatives can be obtained. BHC vapor in a mixture with oxygen (air) and chlorine at 470 °C in the presence of a catalyst containing alumina, copper chloride, and potassium chloride yields a mixture of hexachlorobenzene and pentachlorobenzene.

Use ClassificationFood Contaminant -> CONTAMINANT; Food Contaminant -> -> JECFA Functional Classes
General Manufacturing Information · 2 Einträge

Benzene, 1,2,3,4,5-pentachloro-: ACTIVE

Technical grade PCNB /pentachloronitrobenzene/ contains ... less than 0.1% pentachlorobenzene ...

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