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Dichlormethylbenzol

Benzal chloride

HCID 7411
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
29797-40-8
Standard-SMILES
ClC(Cl)c1ccccc1
InChIKey
CAHQGWAXKLQREW-UHFFFAOYSA-N
Summenformel
C7H6Cl2
Durchschnittliche Molmasse
161,03 g/mol
Monoisotopische Masse
159,98465555

Überblick

Benzylidene chloride appears as a colorless oily liquid with a faint aromatic odor. Insoluble in water and denser than water. Strongly irritates skin and eyes. Used to manufacture dyes.

Namen und Bezeichner

Bevorzugter Name
Benzal chloride
IUPAC
dichloromethylbenzene
Lokaler Name
Dichlormethylbenzol
Englischer Name
2,6-Dichlorotoluene
Summenformel
C7H6Cl2
Molmasse
161.03

Namen und Synonyme

Benzal chloride98-87-3(DICHLOROMETHYL)BENZENEBenzylidene chloridealpha,alpha-DichlorotolueneBenzyl dichlorideDichlorophenylmethaneBenzene, (dichloromethyl)-Benzylene chlorideChlorobenzalChlorure de benzylideneDTXSID6025014
Weitere Namen anzeigen
2,6-DCTDichlormethylbenzolar,ar'-DichlorotolueneDICHLOROTOLUENE MIXTURE1,3-DICHLORO-2-METHYLBENZENEDichlorotoluene, isomer mixturedichlorotoluene(flammableliquids,n.o.s.)dichlorotoluene(combustibleliquid,n.o.s.)DICHLOROTOLUENE,TECHNICALGRADEISOMERMIXTURE
Cloruro de bencilidenoToluene, alpha,alpha-dichloro-NSC-7915DTXCID405014222447TR16RefChem:916845202-709-2Dichloromethylbenzene

Datenbank-Bezeichner

CAS

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
1
Schwere Atome
9
Formalladung
0
Komplexität
75

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Halogenated Monoaromatics

Carcinogens

SpringerMaterials PropertiesBoiling point
LogP · 2 Einträge

log Kow= 3.217 (calculated)

3.22

Odor · 2 Einträge

PUNGENT ODOR

FAINT AROMATIC ODOR

Density · 4 Einträge

1.26 (EPA, 1998) - Denser than water; will sink

1.26

Relative density (water = 1): 1.26

1.26 @25 °C

Color/FormCOLORLESS OILY LIQUID
Solubility · 6 Einträge

less than 1 mg/mL at 63 °F (NTP, 1992)

INSOL IN WATER

SOL IN DILUTE ALKALI

> 10% in ethanol

> 10% in ether

Soluble in most org solvents.

Flash Point · 3 Einträge

198 °F (NTP, 1992)

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

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 13.2% (30 of 227) of reports.

Danger

H302 (86.8%): Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Benzene, (dichloromethyl)-

Chemical: Benzene, dichloromethyl-

Benzene, dichloromethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, dichloromethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Benzene, (dichloromethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, (dichloromethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 06-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/15963

Status: Active Update: 03-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11710

Other Safety InformationIMAP assessments - Benzene, (dichloromethyl)-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 3 Einträge

Fire may produce irritating or poisonous gases. Runoff from fire control water may give off poisonous gases and may cause pollution. Cylinder may explode in the heat of fire. Reacts with water to release hydrochloric acid. (EPA, 1998)

Chemie und Industrie

Verwendung und Herstellung

Uses · 4 Einträge

Used in dyes and to make benzaldehyde and cinnamic acid; [Hawley]

IN DYES /FORMER USE/

MANUFACTURE OF BENZALDEHYDE & CINNAMIC ACID. /FORMER USE/

To prepare benzoyl chloride.

ImpuritiesBenzyl chloride, benzaldehyde, benzoic acid, and benzotrichloride are impurities.
U.S. Production · 4 Einträge

2023: 75,000 - <500,000 lb

2023: 1,000,000 - <5,000,000 lb

(1977) AT LEAST 9.13X10+8 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Consumption PatternsESSENTIALLY 100% AS CHEM INTERMEDIATE FOR BENZALDEHYDE.
Industry Uses · 2 Einträge

Processing aids not otherwise specified

Intermediate

Methods of Manufacturing · 3 Einträge

CHLORINATION OF TOLUENE IN THE PRESENCE OF LIGHT & IN THE ABSENCE OF CATALYSTS THAT PROMOTE RING CHLORINATION.

Benzal chloride can be manufactured in 70% yield by chlorination with 2.0-2.2 moles of chlorine per mole toluene.

Benzal choride is ... formed by reaction of dichlorocarbene (CCl2) with benzene.

Formulations/Preparations... Available in USA as a technical grade with minimal purity of 95%.
General Manufacturing Information · 4 Einträge

All Other Chemical Product and Preparation Manufacturing

All Other Basic Organic Chemical Manufacturing

Benzene, (dichloromethyl)-: ACTIVE

Benzene, dichloromethyl-: ACTIVE

Vor- und nachgelagerte Produkte

Zugehörige Reaktionen

11
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 325262
HRID 325262als Eduktuspto-grants-1984_04
Reaktionsgleichung von HRID 442070
HRID 442070als Produktuspto-grants-1977_08
Reaktionsgleichung von HRID 483406
HRID 483406als Eduktuspto-grants-1993_07
Reaktionsgleichung von HRID 637821
HRID 637821als Produktuspto-grants-1985_12
Reaktionsgleichung von HRID 805019
HRID 805019als ProduktTest data from https://doi.org/10.1039/C8SC04228D
Reaktionsgleichung von HRID 1380015
HRID 1380015als Eduktuspto-grants-1986_04
Reaktionsgleichung von HRID 1416985
HRID 1416985als Eduktuspto-grants-1999_06
Reaktionsgleichung von HRID 1416987
HRID 1416987als Eduktuspto-grants-1999_06
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Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
29797-40-8、98-87-3
PubChem CID
7411
DTXSID
DTXSID6025014
ChEMBL
CHEMBL1412576
ChEBI
CHEBI:82273
UNII
222447TR16
EC Number
202-709-2、249-854-8
Nikkaji
J3.986A

93 °C

93 °C c.c.

Boiling Point · 4 Einträge

401 °F at 760 mmHg (EPA, 1998)

205 °C

205 °C

205 °C @760 [mm Hg]

Decompositionwhen heated to decomp ... emits toxic fumes of /hydrogen chloride/.
Melting Point · 4 Einträge

2.48 °F (EPA, 1998)

-16.4 °C

-17 °C

-17 °C

Vapor Density5.6 (technical grade) (NTP, 1992) - Heavier than air; will sink (Relative to Air)

Physikochemische Eigenschaften

Siedepunkt
196 · 196-203 °C(lit.)
Dichte
1.254 g/mL · 1.254 g/mL at 25 °C(lit.)
Dampfdruck
65.3 Pa · 65.3Pa at 25℃
Brechungsindex
20 · n20/D 1.55(lit.)
Wasserlöslichkeit
11.2 mg/L · 11.2mg/L at 20℃
LogP
4.25 · 4.25
CAS Datenbank
29797 · 29797-40-8(CAS DataBase Reference)
EPA chemische Informationen
Dichlorotoluene (29797-40-8)

· Combustible material: may burn but does not ignite readily.

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

Fire PotentialCombustible.
Health Hazards · 2 Einträge

Acute: vapors are highly irritating to eyes. May be fatal if inhaled, swallowed, or absorbed through skin. (EPA, 1998)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards SummaryA severe skin, eye, and respiratory tract irritant; [ICSC] Strong lachrymator; [HSDB] An irritant; Harmful if swallowed; Toxic by inhalation; May cause serious eye damage; Causes general anesthesia in animal experiments; [MSDSonline]
DOT ID and Guide1886 156
Reactive GroupHalogenated Organic Compounds
EC ClassificationSymbol: T; R: 22-23-37/38-40-41; S: (1/2)-36/37-38-45
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
Special Reports · 3 Einträge

USEPA; Chemical Hazard Information Profile: Benzal chloride (Draft) (1982)

ITC/USEPA; Information Review #204 (Draft) (Dichloromethyl)benzene (1980)

USEPA; Health and Environmental Effects Profile for Benzal Chloride (1988) EPA/600/X-85/046. /Includes/ listings of hazardous constituents of a wide range of waste streams under Section 3001 of the Resource Conservation and Recovery Act (RCRA) and to provide health related limits for emergency actions under Section 101 of the Comprehensive Environmental Response, Compensation and Liability Act (CERCLA).

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Keep unnecessary people away and isolate hazard area. Stay upwind and keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing.

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

Signs and Symptoms of Benzal Chloride Exposure: Benzal chloride may be very irritating to the skin, eyes, and mucous membranes. Eye irritation may be severe, and permanent eye damage may result. Lacrimation (tearing) is common. Other signs and symptoms of acute exposure may include headache, dizziness, weakness, fatigue, irritability, itching of the skin, profuse sweating, insomnia, tremors, unsteadiness, and central nervous system excitation or depression. Gastrointestinal effects may include nausea, vomiting, cramps, anorexia, and diarrhea. Pulmonary edema and disturbance of liver function may also occur.

General First Aid:

Safe StorageSeparated from food and feedstuffs. See Chemical Dangers. Ventilation along the floor.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Disposal Methods · 2 Einträge

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.

Spillage Disposal · 1 Eintrag

Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 1 Eintrag

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and Evacuation · 2 Einträge

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Immediate precautionary measure

Eye PreventionWear face shield.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Benzal chloride hydrolyzes rapidly in water (half-life of 7.4 minutes at 25 °C;) therefore, hydrolysis is expected to be a dominant fate process in moist soil. A theoretical Koc value of 510 can be estimated based on the molecular structure which indicates medium to low soil mobility; however, leaching in moist soils is not expected to be significant since the compound is expected to hydrolyze first. Evaporation of benzal chloride from dry surfaces is expected to occur. (SRC)

AQUATIC FATE: When released to water, benzal chloride will hydrolyze rapidly (half-life of 7.4 minutes at 25 °C and pH 7) and produce benzaldehyde as a hydrolysis product. Due to the rapid hydrolysis, aquatic volatilization, bioconcentration, and adsorption to sediments are not expected to be significant. (SRC)

ATMOSPHERIC FATE: Benzal chloride will react in the vapor-phase with photochemically produced radicals at an estimated half-life rate of 1.84 days. Hydrolysis in the presence of sufficient atmospheric moisture may be possible. (SRC)

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Signs and Symptoms · 4 Einträge

Cough. Laboured breathing. Sore throat.

Redness. Pain.

Redness. Pain.

Burning sensation. Further see Inhalation.

Soil Adsorption/Mobility · 1 Eintrag

Based on molecular topology and quantitative structure-activity relationship analysis, the Koc value for benzal chloride can be estimated to be about 510(1,SRC) which is indicative of medium to low soil mobility(SRC). Due to the relatively rapid hydrolysis in water, leaching of benzal chloride in moist soils is not expected to be significant since it is expected to hydrolyze first(SRC).

Natural Pollution SourcesBenzal chloride has not been reported to occur as such in nature.
Human Toxicity Excerpts · 3 Einträge

STRONG ... LACRIMATOR.

No data clearly relating cancer to exposure to benzal chloride were available to the /IARC/ Working Group. However, benzoyl chloride manufacturing workers, among whom an excess of respiratory cancer has been reported (6 cases in total), were also potentially exposed to benzal chloride.

... Categorized as moderately toxic /by inhalation and ingestion/.

Artificial Pollution Sources · 1 Eintrag

Benzal chloride is produced as a by-product during the commercial manufacture of benzyl chloride(1,2); currently, this is the only source by which benzal chloride is produced industrially(SRC). Fugitive emissions and waste streams from benzyl chloride manufacture are a potential source of benzal chloride(SRC). Since benzal chloride has no current industrial uses(SRC), commercial use of the compound is not a current source of pollution(SRC).

Environmental BiodegradationBenzal chloride was found to readily biodegrade in water(1).
Environmental Bioconcentration · 1 Eintrag

Based on a computer-calculated log Kow value of 3.217(1), the BCF value for benzal chloride can be estimated to be 164(2,SRC). Due to the relatively rapid hydrolysis of benzal chloride in water, bioconcentration in aquatic organisms is not likely to occur(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for benzal chloride at 25 °C can be estimated to be 0.0007 atm cu m/mol by a bond-structural contribution method(1,SRC) which can be used to estimate a volatilization half-life of 5.3 hr from a river 1 m deep flowing at 1 m/sec with a wind velocity of 3 m/sec(2,SRC). However, the hydrolysis half-life of 7.4 minutes at 25 °C indicates that volatilization from water is not significant relative to hydrolysis(SRC ). Benzal chloride fumes in air(3) and has a reported vapor pressure of 0.3 mm Hg at 20 °C(4) which suggests that evaporation from dry surfaces will occur(SRC).

Non-Human Toxicity Excerpts · 5 Einträge

Benzal chloride (redistilled commercial material, purity & impurities not specified) has been reported to be mutagenic in reversion assays using Salmonella typhimurium strain TA100 (the only strain tested) & in Escherichia coli strain WP2 hcr; mutagenicity required metabolic activation by a microsomal fraction of the livers of rats induced by Arochlor 1254. It was also positive in a rec-assay Bacillus subtilis.

The LC16, LC50, & LC84 values for 2 hr exposures to benzal chloride were 160, 400, & 1000 mg/cu m (24, 61 & 152 ppm), respectively, for rats, & 80, 210, & 550 mg/cu m (12, 32 & 84 ppm), respectively for mice. The order of decreasing toxicity among the chlorinated toluenes was: benzotrichloride > benzal chloride > benzyl chloride. Thus, in single 2 hr exposure of mice & rats to 100 mg/cu m (15.2 ppm), all 3 cmpd produced central nervous system excitation, irritation of the eyes & respiratory mucosa & slowed respiration in order of activity described above. Hyperemia of the extremities was also noted; at 1000 mg/cu m (152 ppm) mice exhibited motor automatism, & rats showed twitching of peripheral muscles. When rats were exposed to 100 mg/cu m of each of the compounds in inhalation chamber, continuously for 1 mo, the degree of wt loss was related to the same order of activity as in the acute studies.

... Two groups, each consisting of 19 or 20 female ICR mice, 7 wk old ... were given skin applications of 25 ul (22 mg) benzene (controls) or 25 ul of a 9.2% soln of benzal chloride in benzene (vol/vol; 2.9 mg benzal chloride /treatment; about 75-100 mg/kg body weight, assuming body weights of 24-40 g/ twice weekly for 50 wk (total dose, about 289 mg/animal). All mice were killed at wk 82. ... No skin tumor was observed in any control. Of the 19 benzal chloride treated mice, 14 (74%) had died by the end of the experiment; 12 (63%) developed tumors: 9 with squamous cell carcinomas of the skin (p < 0.01), 2 with skin fibrosarcoma, & 1 with a lymphoma; lung adenomas were reported in 5 treated mice & 2 controls. /Fukuda et al, 1981/.

Benzal chloride and benzotrichloride induced mutation and DNA damage in bacteria.

For more Non-Human Toxicity Excerpts (Complete) data for BENZAL CHLORIDE (6 total), please visit the HSDB record page.

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

As stipulated in 40 CFR 261.33, when dichloromethyl(benzene) 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 RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA.
Atmospheric Standards · 1 Eintrag

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzyl dichloride is produced, as an intermediate or final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 2 Einträge

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; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzal chloride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 1886
risk_code
22-23-37/38-40-41
hazard_code
T
safety_code
26-36/37/39-45
hazard_class
6.1
packing_group
II

Nachgelagerte Produkte

BenzylchloridMethyl-2-chlormethylbenzoat