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
Show more names
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
- Formal charge
- 0
- Complexity
- 19.2
Experimental & physicochemical properties
Solvents
Solvents -> Chlorinated Aliphatics
Solvents -> Chlorinated Aliphatics
Density
1.2837 at 68 °F (NTP, 1992) - Denser than water; will sink
1.2837 g/cu cm at 20 °C
1.2837 @ 20°C
Color/Form
Liquid
Colorless liquid
Solubility
1 to 5 mg/mL at 61 °F (NTP, 1992)
In water, 6.41X10+3 mg/L at 25 °C
In water, 3.5X10+3 mg/L at 25 °C
Slightly soluble in water
Miscible with ethanol, ethyl ether, acetone; very soluble in benzene, chloroform
Flash Point
39 °F (NTP, 1992)
2 °C
6.0 °C (42.8 °F) - closed cup
2.2 to 3.9 °C (closed cup)
Boiling Point
140 °F at 760 mmHg (NTP, 1992)
60 °C
BP: 58-60 °C
60.1 °C @760 [mm Hg]
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
- solubility
- soluble in Chloroform
- form
- Liquid
- color
- Clear colorless
- Water Solubility
- 3.5 g/L · 3.5g/L(25 ºC)
- Specific Heat Capacity
- 1.2 J/ · Cp(liquid): 1.2 J/(g·K); Cp(gas): 0.67 J/(g·K), at 25℃
- Merck
- 14 · 14,92
- BRN
- 1071208 · 1071208
- Henry's Law Constant
- 2.3 · 2.3×10-3 mol/(m3Pa) at 25℃, Schwardt et al. (2021)
- Exposure limits
- 800 mg/m3 · PC-TWA: 800 mg/m3
- Dielectric constant
- 9.2 · 9.1999999999999993
- Stability
- Volatile
- InChI
- 1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1-
- InChIKey
- KFUSEUYYWQURPO-UPHRSURJSA-N
- EPA Primary Drinking Water Standard
- 0.07 · MCL:0.07,MCLG:0.07
- SMILES
- Cl\C=C/Cl
- CAS DataBase Reference
- 156 · 156-59-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-4
- FDA UNII
- 9 G15JYD · FYO9G15JYD
- EPA Substance Registry System
- -1 · cis-1,2-Dichloroethylene (156-59-2)
- Toxicological Profile|ATSDR
- -1 · CIS-1,2-DICHLOROETHYLENE|Toxicological Profile|ATSDR
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H302+H332-H315-H412
- Precautionary statements
- 210 · P210-P233-P273-P301+P312-P303+P361+P353-P304+P340+P312
- PPE
- Eyeshields, Faceshields, Gloves
- Hazard Codes
- F,Xn,T
- Risk Statements
- 11 · 11-20-52/53-39/23/24/25-23/24/25
- Safety Statements
- 7 · 7-16-29-61-45-36/37
- RIDADR
- 1150 · UN 1150 3/PG 2
- OEB
- A
- OEL
- 200 ppm; · TWA: 200.0 ppm; 790.0 mg/m3
- WGK Germany
- 2 · 2
- RTECS
- 9420000 · KV9420000
- F
- 1 · 1-8-10
- TSCA
- TSCA listed
- HazardClass
- 3.1 · 3.1
- PackingGroup
- II
- HS Code
- 29032990 · 29032990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 InhalationAcute · Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Flam. Liq. 2Skin Irrit. 2
- Hazardous Substances Data
- 156 · 156-59-2(Hazardous Substances Data)
- Toxicity
- 20 gm/m3/6H · cat,LCLo,inhalation,20gm/m3/6H (20000mg/m3),BEHAVIORAL: GENERAL ANESTHETICBEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD,Archiv fuer Hygiene und Bakteriologie. Vol. 116, Pg. 131, 1936.
Safety & regulation
GHS classification
GHS Classification
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
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
Fire Potential
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.
Hazards Summary
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.
Special Reports
USEPA; Health Effects Assessment for cis-1,2-dichloroethylene (1984) EPA/540/1-86/015
Rev Environ Contam Toxicol 106: 93-101 (1988). A review article on the pharmacokinetics of cis-1,2-dichloroethylene.
Safety & protection
First Aid
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
200.0 [ppm]
200.0 [ppm]
Fire Fighting Procedures
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
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
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.
Disposal Methods
SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.
Preventive Measures
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.
Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Use explosion-proof equipment. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
For more Preventive Measures (Complete) data for cis-1,2-Dichloroethylene (7 total), please visit the HSDB record page.
Threshold Limit Values (TLV)
200.0 [ppm]
200.0 [ppm]
8 hr Time Weighted Avg (TWA): 200 ppm.
Peak Exposure Recommendation: Transient increases in workers' exposure levels may exceed 3 times the value of the TLV-TWA level for no more than 15 minutes at a time, on no more than 4 occasions spaced 1 hour apart during a workday, and under no circumstances should they exceed 5 times the value of the TLV-TWA level. In addition, the 8-hour TWA is not to be exceeded for an 8-hour work period.
Toxicology
Body Burden
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
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
Dermal (Skin), Immunological (Immune System), Ocular (Eyes)
Urinary
Health Effects
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)
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), a reported Koc of 49(2), indicates that cis-1,2-dichloroethylene is expected to have very high mobility in soil(SRC). Volatilization of cis-1,2-dichloroethylene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.08X10-3 atm-cu m/mole(3). cis-1,2-Dichloroethylene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 200 mm Hg at 25 °C(4). A 0% of Theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is an important environmental fate process in soil(SRC). The half-life of cis-1,2-dichloroethylene in two soil field biodegradation studies was 17 and 25 days(6).
AQUATIC FATE: Based on a classification scheme(1), a reported Koc of 49(2), indicates that cis-1,2-dichloroethylene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.08X10-3 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hours and 4 days, respectively(SRC). cis-1,2-dichloroethylene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5). According to a classification scheme(6), an estimated BCF of 8(SRC), from its log Kow of 1.86(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. The half-life of cis-1,2-dichloroethylene in two aquatic field biodegradation studies was 36 and 47 days(9). The concentration of cis-1,2-dichloroethylene was reduced to <2% and to trace concentrations after 16 and 40 weeks, respectively, when incubated in a serum bottle at 17 °C with methanogenic aquifer material obtained adjacent to a landfill site(10); this indicates that anaerobic biodegradation is an important environmental fate process in groundwater(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cis-1,2-dichloroethylene, which has a vapor pressure of 200 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cis-1,2-dichloroethylene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone and nitrate radical(SRC); the half-lives for these reactions in air are estimated to be 6.1, 180 and 240 days(SRC), calculated from its rate constants of 2.62X10-12(3), 6.3X10-20(4) and 1.38X10-16 cu cm/molecule-sec(5), respectively. cis-1,2-Dichloroethylene does not contain chromophores that absorb at wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
cis-1,2-Dichloroethylene was not detected in 70 different food type samples (whole milk, vanilla ice milk, American, Swiss, cheddar or cream cheese, sour cream, vanilla ice cream, sherbet, popsicles, mixed nuts, ground beef, homemade meatloaf, chuck roast, pork bacon, hot dogs, bologna, salami, tuna, fish sticks, quarter pounder, chicken nuggets, fried chicken, french fries, quarter pounder/cheese, taco/tostada, cheese pizza, cheese/pepperoni pizza, strawberries, raisins, avocados, tomatoes, bananas, apples, oranges, coleslaw, scrambled eggs, peanut butter, cream style corn, white bread, blueberry muffins, corn chips, potato chips, fruit-flavored cereal, graham crackers, butter crackers, commercial chocolate cake, chocolate snack cake, cake doughnuts, brownies, sugar cookies, sweet rolls, chocolate chip cookies, sandwich cookies, apple pie, milk chocolate candy bar, caramels, cola, low-calorie cola, fruit-flavored drink, orange juice, margarine, butter, olive/safflower oil, milk or soy-based infant formula, strained/junior beef, carrots or apple juice) during the US FDA Total Diet Program that was run 1996 to 2000 with samplings done four times a year(1).
Adverse Effects
Neurotoxin - Acute solvent syndrome
Neurotoxin - Acute solvent syndrome
Toxicity Summary
IDENTIFICATION AND USE: cis-1,2-Dichloroethylene is a colorless liquid. The cis-isomer of 1,2-dichloroethylene has had only limited use as a solvent and chemical intermediate. It has not developed wide industrial usage in the US partly because of its flammability. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: cis-1,2-Dichloroethylene at 16,000 ppm anesthetized rats in 8 minutes and killed them in 4 hours. The results of repeated exposures of cats and rabbits to vapor concentration of 0.16 to 0.19% in the air was reported. Animals exposed to cis-1,2-dichloroethylene at this concentration showed loss of appetite and some respiratory irritation but no histological changes. cis-1,2-Dichloroethylene was administered daily by gavage to male and female rats at the following dose levels: 1.0, 3.0, 10.0 and 22.0 mmol/kg/day for 14 days. Doses gavaged during the 90-day subchronic study were 0.33, 1.00, 3.00 and 9.00 mmol/kg/day. There were no compound-related deaths or histopathological changes demonstrated. Significant increases in relative liver weights were seen after 14- and 90-days of treatment in both sexes. This study demonstrates some indication of toxicity at subacute and subchronic exposure levels as low as 0.33 mmol/kg/day. Implications of liver abnormalities were demonstrated at an exposure level of 1 mmol/kg/day while kidney abnormalities (relative weights) were demonstrated at an exposure level of 0.33 mmol/kg/day. 1,2-dichloroethylene cis and trans were tested for their ability to induce point mutation, mitotic gene conversion and mitotic recombination in a diploid strain (D7) of the yeast Saccharomyces cerevisiae in a suspension test with and without a mammalian microsomal activation system. In this test both cis and trans isomers were toxic but not genetically active even with metabolic activation. The clastogenic potential of cis-1,2-dichloroethylene was examined using Chinese hamster cells in culture and showed no significant increase in the incidence of chromosome aberrations when used with and without metabolic activation. cis-1,2-Dichloroethylene bound to the active site of hepatic microsomal cytochrome P450 with production of a type-I difference spectrum and stimulated co-inhibitable hepatic microsomal NADPH oxidation.
Trans-1,2-dichloroethene is a volatile, lipophilic molecule that easily moves through the respiratory and gastrointestinal systems. It has a high affinity for lipids and blood, but little accumulation in tissues. 1,2-Dichloroethene isomers inhibit liver enzymes involved in metabolism and may increase the “toxic” response to other chemicals. Reactive metabolites of trans-1,2-dichloroethene modify the heme moiety of hepatic microsomal cytochrome P-450, resulting in a loss of both cytochrome P-450 and heme. Trans-1,2-dichloroethene can also mixed-function oxidase activities. Metabolism of trans-1,2-dichloroethene can lead to dose-related decrease in the levels of serum glutamicoxaloacetic transaminase (SGOT) and serum glutamic-pyruvic transaminase (SGPT). (L585)
Ecotoxicity Excerpts
/AQUATIC SPECIES/ The responses of 27 organic compounds, mainly chloromethanes, -ethanes, -ethenes, and -phenols, were investigated by exposing rainbow trout fingerlings to low microgram-per-liter concentrations in a darkened flow-through system for up to 1 hr. Responses by the fish were followed continuously by observing ventilation rates (frequency and amplitude), swimming patterns, and general activity using the low-voltage electric fields generated by the fishes' activity. The lowest level of response was found for trichloroethylene at 5 ug/L. Dichloromethane, 1,1- and 1,2-dichloroethane, 1,1,1- and 1,1,2-trichloroethane, cis-1,2-dichloroethylene, 1,3-dichloropropene, and allyl acetate were responded to at concentrations of 10 ug/L, carbon tetrachloride at 15 ug/L, and 4-chlorophenol and 2,4-dichlorophenol at levels of 30 ug/L. Unsubstituted phenol was not responded to at levels of up to 50 ug/L.
Regulatory information
CERCLA Reportable Quantities
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/
State Drinking Water Guidelines
(ME) MAINE 70 ug/l
(MN) MINNESOTA 50 ug/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
- rtecs
- KV9420000
- ridadr
- UN 1150 3/PG 2
- hs_code
- 29032990
- Toxicity
- cat,LCLo,inhalation,20gm/m3/6H (20000mg/m3),BEHAVIORAL: GENERAL ANESTHETICBEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD,Archiv fuer Hygiene und Bakteriologie. Vol. 116, Pg. 131, 1936.
- risk_code
- 11-20-52/53-39/23/24/25-23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xn,T
- safety_code
- 7-16-29-61-45-36/37
- hazard_class
- 3.1
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H225-H302+H332-H315-H412
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Flam. Liq. 2Skin Irrit. 2
- Precautionary statements
- P210-P233-P273-P301+P312-P303+P361+P353-P304+P340+P312
- Hazardous Substances Data
- 156-59-2(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Biological Half-Life
/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
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
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
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
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]
Methods of Manufacturing
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.
General Manufacturing Information
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers62 total
Additional notes
DefinitionChEBI: Cis-1,2-dichloroethene is a 1,2-dichloroethene.
Related reactions
Compound notes
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