cis-1,2-Dichloroethylene

HCID 643833

Basic information

CAS
156-59-2
Standard SMILES
Cl/C=C\Cl
InChIKey
KFUSEUYYWQURPO-UPHRSURJSA-N
Molecular formula
C2H2Cl2
Average molar mass
96.94 g/mol
Monoisotopic mass
95.95335542

Overview

1, 2-Dichloroethene, also called 1, 2-dichloroethylene, is a highly flammable, colorless liquid with a sharp, harsh odor. It is used to produce solvents and in chemical mixtures. You can smell very small amounts of 1, 2-dichloroethene in air (about 17 parts of 1, 2-dichloroethene per million parts of air [17 ppm]). There are two forms of 1, 2-dichloroethene; one is called cis-1, 2-dichloroethene and the other is called trans-1,2-di-chloroethene. Sometimes both forms are present as a mixture.

Names & identifiers

Preferred name
cis-1,2-Dichloroethylene
IUPAC
(Z)-1,2-dichloroethene
English name
cis-1,2-Dichloroethylene
Molecular formula
C2H2Cl2
Molecular weight
96.94

Names & synonyms

CIS-1,2-DICHLOROETHYLENEcis-1,2-Dichloroethene156-59-2(Z)-1,2-Dichloroethylenecis-DichloroethyleneAcetalyne dichlorideAcetylene dichloride, cis-Ethene, 1,2-dichloro-, (Z)-Ethylene, 1,2-dichloro-, (Z)-cis-1,2-dceHCC 1130cCCRIS 4605
Show more names
cis-Dichloroethenecis-DCEcisdichloroethylene1,2-cis-Dichloroethenecis-1,2-Dichlorethylencis-1,2-dichlorethylene
HSDB 5656R 1130cNSC 6149Ethene, 1,2-dichloro-, (1Z)-EINECS 205-859-7BRN 1071208AI3-28863CHEBI:28805

Database identifiers

CAS
156-59-2
PubChem CID
643833
DTXSID
DTXSID2024030
ChEMBL
CHEMBL1441128
ChEBI
CHEBI:28805
UNII
FYO9G15JYD
EC Number
205-859-7
Nikkaji
J2.558E

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
4

Experimental & physicochemical properties

Chemical ClassesVolatile Organic Compound (VOC)
Solvents · 2 items

Solvents -> Chlorinated Aliphatics

Solvents -> Chlorinated Aliphatics

SpringerMaterials PropertiesCoriolis coupling
PesticidesPesticide -> EPA IRIS
LogPlog Kow = 1.86
OdorSweetish

Physicochemical properties

Melting point
-80 °C · -80 °C (lit.)
Boiling point
60 °C · 60 °C (lit.)
Density
1.284 g/mL · 1.284 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.449(lit.)
Flash point
43 °F · 43 °F
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 4 items

Chemical: Ethene, 1,2-dichloro-, (Z)-

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

Ethene, 1,2-dichloro-, (1Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethene, 1,2-dichloro-, (1Z)- 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)

Ethene, 1,2-dichloro-, (1Z)-: HSNO Approval: HSR001121 Approved with controls

DOT LabelFlammable Liquid
Fire HazardsExcerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious); polymerization hazard]:
Fire Potential · 1 item

Sometimes thought to be nonflammable, however, it is a dangerous fire hazard when exposed to heat or flame. Reaction with solid caustic alkalies or their concentrated solutions produces chloracetylene gas, which ignites spontaneously in air.

Health HazardsExcerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious); polymerization hazard]:
Hazards Summary · 3 items

1, 2-Dichloroethene, also called 1, 2-dichloroethylene, is a highly flammable, colorless liquid with a sharp, harsh odor. It is used to produce solvents and in chemical mixtures. You can smell very small amounts of 1, 2-dichloroethene in air (about 17 parts of 1, 2-dichloroethene per million parts of air [17 ppm]). There are two forms of 1, 2-dichloroethene; one is called cis-1, 2-dichloroethene and the other is called trans-1,2-di-chloroethene. Sometimes both forms are present as a mixture.

Liver injury observed in acute animal toxicology studies; [ACGIH] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; [ICSC]1,2-Dichloroethylene (UN1150) has warning of explosive polymerization; [ERG 2016] See trans-1,2-Dichloroethylene and cis-1,2-Dichloroethylene.

Causes general anesthesia, convulsions, and fatty liver degeneration in inhalation lethal-concentration studies of rodents; [RTECS] Irritating and narcotic at high vapor concentrations; May cause irritation and CNS depression; Liver and kidney injury observed in experimental animals; [NTP] May polymerize; A moderate skin and eye irritant; Inhalation of high concentrations may have narcotic effects; [Acros Organics MSDS] See 1,2-Dichloroethylene, all isomers.

Safety & protection

Fire FightingExcerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious); polymerization hazard]:
First Aid · 1 item

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.

Exposure Control and Personal Protection · 2 items

200.0 [ppm]

200.0 [ppm]

Fire Fighting Procedures · 3 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

Storage Conditions · 1 item

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature 2-8 °C. Handle and store under inert gas. Air and moisture sensitive. Light sensitive.

Cleanup Methods · 2 items

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

A mixed culture containing methane-utilizing bacteria was obtained. Two chlorinated ethenes, cis- and trans-1,2-dichloroethylene, were shown to degrade to chlorinated products, which appear to degrade further.

Toxicology

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1 item

cis-1,2-Dichloroethylene was not detected (detection limit 0.015 ppb) in blood samples collected from the general population, number of samples, sample dates and locations were not available(1). cis-1,2-Dichloroethylene was one of 110 chemicals monitored in blood and urine samples of 321 firefighters that responded to the Sept 11, 2001 World Trade Center collapse and 47 firefighters that were used as a control group(2). cis-1,2-Dichloroethylene was determined to be not statistically different for these groups(2).

Treatment · 1 item

Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of seizures, administer a benzodiazepine IV. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes in case of eye exposure. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (T36)

Target Organs · 2 items

Dermal (Skin), Immunological (Immune System), Ocular (Eyes)

Urinary

Health Effects · 1 item

Breathing trans-1,2-DCE can cause sever liver and kidney damages, pulmonary capillary hyperemia, as well as alveolar septal distention; depression of the central nervous sustem can occur; moderate iritis and conjunctivitis can follow eye exposure; dermatitis and irritation of mucous membranes can follow dermal exposure. Symptoms associated with lethal oral doses included decreased activity, ataxia, suppressed or total loss of righting reflex, and depressed respiration. (L585)

Ecotoxicity ValuesLC50; Species: Lepomis machrochirus (bluegill); Conditions: static unmeasured bioassay; Concentration: 135,000 ug/L for 96 hr

Regulatory information

RCRA Requirements/SRP: The cis- isomer is not a listed hazardous waste./
CERCLA Reportable Quantities · 1 item

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 1000 lb or 454 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). /trans-1,2-Dichloroethylene/

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. /Dichloroethylenes (1,1-, and 1,2-dichloroethylene)/
State Drinking Water Standards(CA) CALIFORNIA 6 ug/l
State Drinking Water Guidelines · 2 items

(ME) MAINE 70 ug/l

(MN) MINNESOTA 50 ug/L

Federal Drinking Water StandardsMaximum contaminant levels (MCL) for organic contaminants apply to community and non-transient, non-community water systems: cis-1,2-Dichloroethylene, MCL 0.07 mg/L.

Safety data

F
1-8-10
OEB
A
OEL
TWA: 200.0 ppm; 790.0 mg/m3
PPE
Eyeshields, Faceshields, Gloves
wgk
2
tsca
TSCA listed

Chemistry & industry

Pharmacology

Biological Half-Life · 2 items

/Researchers/ have estimated elimination rate constants for the disappearance from human blood of certain halogenated VOCs, including cis-1,2-DCE. Estimates were based on decay of exhaled breath concentrations following a 10-minute shower exposure to contaminated water and published blood/air partition coefficients for the VOC in question. Two volunteers were exposed in separate showering episodes, in which estimated total absorbed doses of cis-1,2-DCE were 1.19 and 2.34 ug, respectively. ... In the first fast-elimination compartment (presumed to represent disappearance of cis-1,2-DCE from the blood), elimination half-lives of 0.82 and 2.37 minutes were estimated in the two subjects; corresponding half-lives in the slower, highly perfused tissue compartment were 8.96 and 29.33 minutes, respectively. These limited data suggest the potential for variability in the elimination of cis-1,2-DCE in humans.

Trans- and cis-1,2-dichloroethylene (DCE) isomers inhibit their own metabolism in vivo by inactivation of the metabolizing enzyme, presumably the cytochrome P450 isoform, CYP2E1. In this study, we examined cytochrome P450 isoform-specific inhibition by three chloroethylenes, cis-DCE, trans-DCE, and trichloroethylene (TCE) /in rats/, and evaluated several kinetic mechanisms of enzyme inhibition with physiological models of inhibition. Trans-DCE was more potent than cis-DCE, and both were much more effective than TCE in inhibiting CYP2E1. The kinetics of in vitro loss of p-nitrophenol hydroxylase (pNP-OH) activity (a marker of CYP2E1) in microsomal incubations and of the in vivo gas uptake results were most consistent with a mechanism in which inhibition of the metabolizing enzyme (CYP2E1) was presumed to be related to interaction of a reactive DCE metabolite with remaining substrate-bound, active CYP2E1. The kinetics of inhibition by TCE, a weak inhibitor in vitro, were very different from that of the dichloroethylenes. With TCE, parent compound concentrations influenced enzyme loss. Trans-DCE was a more potent inhibitor of CYP2E1 than cis-DCE based on both in vivo and in vitro studies. Quantitative differences in the inhibitory properties of the 1,2-DCE isomers may be due to the different stability of epoxides formed from bioactivation by CYP2E1. Epoxide intermediates of DCE metabolism, reacting by water addition, would yield dialdehyde, a potent cross-linking reagent.

Metabolism/Metabolites · 6 items

Cis- and trans-1,1-dichloroethylene bound to the active site of hepatic microsomal cytochrome P-450 with the production of a Type I difference spectrum and stimulated CO-inhibitable hepatic microsomal NADPH oxidation. Incubation of cis- and trans-1,2-dichloroethylene plus hepatic microsomes, NADPH-generating system-EDTA resulted in the production of measurable levels of 2,2-dichloroethanol and dichloroacetaldehyde but not of 2-chloroethanol, chloroacetaldehyde or chloroacetic acid and, also, resulted in decreased levels of hepatic microsomal cytochrome P-450 and heme. In addition, dichloroacetic acid was produced from trans-dichloroethylene under these experimental conditions. The omission of any component of the incubation mixture eliminated the above effects, while the inclusion of SKF-525A, metyrapone or CO:O2 (80, v/v) diminished these effects. The effects of beta-naphthoflavone and phenobarbital pretreatment on the values of Ks, delta Amax, Km and Vmax for the binding and metabolism of the 1,2-dichloroethylenes are reported. The binding and metabolism of the 1,2-dichloroethylenes and the 1,2-dichloroethylene-mediated inactivation of cytochrome P-450 were enhanced per mg of microsomal protein, but generally not per nmole of cytochrome P-450 by prior induction with beta-naphthoflavone or phenobarbital. It is concluded that multiple forms of hepatic microsomal cytochrome P-450 bind and metabolize the 1,2-dichloroethylenes. The role of cytochrome P-450 in the metabolic activation of the dichloroethylenes is considered.

Rats exposed to cis-1,2-dichloroethylene exhaled acetone at a rate of 1.95 umol/hr/kg.

Similarities and differences have been observed in the metabolism of cis- and trans-1,2-dichloroethene. Both isomers have been shown to bind to the active site of hepatic cytochrome P-450. In addition, classic inhibitors of cytochrome P-450 have been shown to inhibit the production of dichloroacetaldehyde from both isomers. The binding and metabolism of 1,2-dichloroethene do not appear to be specific for any one form of cytochrome P-450. The cis isomer had a 4-fold greater rate of turnover in hepatic microsomes in vitro than the trans isomer. This is consistent with studies on isolated perfused rat livers, where metabolism of the cis isomer occurred at a greater rate than metabolism of the trans isomer. In addition, differences between cis- and trans-1,2-dichloroethene in the rates of formation of dichloroethanol and dichloroacetic acid have been reported in rat hepatocytes.

Animal studies have shown that metabolism of the cis isomer occurs faster than metabolism of the trans isomer, and the cis isomer frequently inhibits activity or destroys cytochrome P-450 levels, while the trans isomer frequently increases the enzyme levels.

For more Metabolism/Metabolites (Complete) data for cis-1,2-Dichloroethylene (8 total), please visit the HSDB record page.

Metabolism of trans-1,2-dichloroethene is initially catalyzed by hepatic microsomal cytochrome P-450. This metabolism is believed to involve epoxidation of the ethylene double bond, forming dichlorinated epoxides. Dichlorinated epoxides, in turn, can undergo a non-enzymatic rearrangement. Studies on the metabolism of 1,2-dichloroethene by hepatic microsomes and hepatocytes provide evidence to suggest that dichloroacetaldehyde is the predominant metabolite of microsomal cytochrome P-450 and that it, in turn, is extensively converted to dichloroethanol and dichloroacetate by cytosolic and/or mitochondrial aldehyde and alcohol dehydrogenases present in hepatocytes. (L585)

Absorption, Distribution and Excretion · 2 items

In an experiment using isolated perfused liver from female Wistar rats, at equimolar concentrations in the perfusate (with chlorinated ethylenes added as vapors at constant rates that allowed for steady-state conditions of substrate uptake and conversion), uptake for cis-1,2-DCE was about 3 times faster than for trans-1,2-DCE.

/Researchers/ have estimated elimination rate constants for the disappearance from human blood of certain halogenated VOCs, including cis-1,2-DCE. Estimates were based on decay of exhaled breath concentrations following a 10-minute shower exposure to contaminated water and published blood/air partition coefficients for the VOC in question. Two volunteers were exposed in separate showering episodes, in which estimated total absorbed doses of cis-1,2-DCE were 1.19 and 2.34 ug, respectively. The kinetics of elimination of the parent compound from breath suggested the existence of two biological distribution compartments, which were presumed to represent the blood and 'highly perfused tissues' (e.g., liver). In the first fast-elimination compartment (presumed to represent disappearance of cis-1,2-DCE from the blood), elimination half-lives of 0.82 and 2.37 minutes were estimated in the two subjects; corresponding half-lives in the slower, highly perfused tissue compartment were 8.96 and 29.33 minutes, respectively. These limited data suggest the potential for variability in the elimination of cis-1,2-DCE in humans.

Uses & manufacturing

Uses · 6 items

Used as a solvent and chemical intermediate; [ACGIH] Used as a refrigerant, degreaser, dry cleaning agent, and solvent for perfumes, adhesives, lacquers, oils, and resins; [HSDB] Only the trans isomer is commercially available in the US--used for precision cleaning of electronic components and a small amount used as a blowing agent for specialty foams; [EPA Toxicological Review, 2010]

Metal Degreasing [Category: Clean]

Used as a solvent (fats, phenol, camphor, etc.) and as an intermediate; [Merck Index] Also used to make rubber, as a refrigerant, an additive to dye and lacquer solutions, to retard fermentation, and in medicines, perfumes, and thermoplastics; [NTP]

Painting (Solvents) [Category: Paint]

Cis- and trans-isomers of 1,2-dichloroethylene have had only limited use as solvents and chemical intermediates. Neither of the isomers has developed wide industrial usage in the USA partly because of their flammability.

1,2-Dichloroethylenes can be used as solvent for waxes, resins, lacquers, and thermoplastics; for the extraction of oil and fats from fish and meat; for vapor degreasing, as surface cleaning agent; for the extraction of rubber, as foam blowing additive; as refrigerant; in the manufacture of pharmaceuticals, and as source of HCl in silicone etching. /1,2-Dichloroethylenes/

U.S. Production · 3 items

2023: 50,000 - <250,000 lb

(1977) AT LEAST 5.0X10+8 G (CAPTIVE PRODN)

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5491]

Industry UsesIntermediate
Methods of Manufacturing · 3 items

Dichloroethylenes (cis: [156-59-2]; trans: [156-60-5]) often occur as an isomeric mixture during the production of chlorinated hydrocarbons, where they are produced by sidereactions, e.g., by thermal decomposition of 1,1,2-trichloroethane or from acetylene by chlorine addition. The isomers can be separated by fractional distillation.

In the thermal dehydrochlorination of 1,1,2-trichloroethane, the 1,2-dichloroethylenes are obtained together with the 1,1-isomer. With increasing temperature, formation of the 1,2-isomers increases. The trans isomer is preferentially formed. With catalysts, the individual ratios can be varied to some extent. /1,2-Dichloroethylenes/

The chlorination of acetylene with activated carbon catalyst yields almost exclusively the cis isomer. An excess of acetylene is required to suppress the formation of tetrachloroethane. Instead of carbon, mercury and iron salts can be used.

Use ClassificationChemical Classes -> Volatile organic compounds
General Manufacturing Information · 5 items

All Other Basic Organic Chemical Manufacturing

Ethene, 1,2-dichloro-, (1Z)-: ACTIVE

Because of the relatively low demand for 1,2- dichloroethylenes they are not deliberately produced in large quantities. They occur as byproducts in some processes, such as the production of vinyl chloride, trichloroethylene, and tetrachloroethylene and can be withdrawn and purified if required. /1,2-Dichloroethylenes/

The 1,2-dichloroethylenes are commercially unimportant, because they do not polymerize, have relatively low boiling points, and can form explosive mixtures with air. In applications where dichloroethylenes could be used as solvents and for low temperature extraction processes, they have been replaced by methylene chloride, which has a higher solvency, is readily available, and is based on less expensive feedstocks. /1,2-Dichloroethylenes/

Trans isomer is more widely used in industry than either the cis isomer or the commercial mixture.

Applications · 3 items

Usescis-DCE and other chloroethenes like tetrachloroethene (PCE), trichloroethene (TCE), and vinyl chloride (VC) are extensively used as solvents in different dry cleaning and metal degreasing industries.

Usescis-1,2-Dichloroethylene (cis-1,2-DCE) is generally used in the preparation of various enediynes for Bergman cyclization. Applications include the synthesis of:2-(6-substituted 3(Z)-hexen-1,5-diynyl)anilines to prepare corresponding substituted carbazoles.(Z)-1-aryl-3-henen-1,5-diynes to obtain the corresponding aryl substituted benzotriazoles.It is used as a linker to synthesize boron-dipyrromethene (BODIPY)-based photosensitizer for photodynamic therapy (PDT). cis-1,2-DCE can also be used as a precursor to synthesize intermediates of sporolide B.

General DescriptionA clear colorless liquid with an ether-like odor. Flash point 36-39°F. Denser than water and insoluble in water. Vapors heavier than air. Used in the making of perfumes.

Suppliers62 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海比阳实业有限公司+86-21-52699951; +8613917686115 · [email protected]

Additional notes

DefinitionChEBI: Cis-1,2-dichloroethene is a 1,2-dichloroethene.

Related reactions

17 records

Compound notes

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