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1,4-Dichloro-cis-2-butene

HCID 6432115
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Basic information

CAS
1476-11-5
Standard SMILES
ClC/C=C\CCl
InChIKey
FQDIANVAWVHZIR-UPHRSURJSA-N
Molecular formula
C4H6Cl2
Average molar mass
124.99 g/mol
Monoisotopic mass
123.98465555

Overview

1,4-Dichloro-2-butene can cause cancer according to The Environmental Protection Agency (EPA).

Names & identifiers

Preferred name
1,4-Dichloro-cis-2-butene
IUPAC
(Z)-1,4-dichlorobut-2-ene
English name
cis-1,4-Dichloro-2-butene
Molecular formula
C4H6Cl2
Molecular weight
125

Names & synonyms

cis-1,4-Dichloro-2-butene1,4-DICHLORO-cis-2-BUTENE2-Butene, 1,4-dichloro-, (Z)-cis-1,4-dichlorobut-2-eneCCRIS 2651HSDB 5832(Z)-1,4-Dichlorobutene2-Butene, 1,4-dichloro-, cis-EINECS 216-021-5BQS2752I902-Butene, 1,4-dichloro-, (2Z)-1,4-DICHLORO-2-BUTENE, CIS-
Show more names
oro-2-butenecis-1,4-DichLcis-1,4-Dichloro-2-bPyridoxine Impurity 61,4-Dichlor-2-butencisCIS-1,4-DICHLOROBUTENE4-dichloro-(z)-2-buten4-dichloro-cis-2-buten
1,4-DICHLORO-2-BUTENE, (2Z)-cis1,4Dichloro2buteneRefChem:4167292Butene, 1,4dichloro, cis2Butene, 1,4dichloro, (Z)1476-11-5(Z)-1,4-dichlorobut-2-eneCIS 1,4-DICHLOROBUTENE

Database identifiers

CAS
1476-11-5、764-41-0
PubChem CID
6432115
DTXSID
DTXSID3027405
ChEMBL
CHEMBL3182662
UNII
BQS2752I90
EC Number
216-021-5
Nikkaji
J7.746A

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
2
Heavy atoms
6
Formal charge
0
Complexity
34.8

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Halogenated Aliphatics, Unsaturated
SpringerMaterials PropertiesSchoenflies notation
Density1.188 @ 25 °C/4 °C
Viscosity0.0035678 Pa-sec @ melting point
Color/FormColorless liquid
Solubility · 2 items

Sol in alcohol, ether, acetone, benzene

In water , 580 mg/l @ 25 °C

Boiling Point152.5 °C
DecompositionDecomposition vapors contain phosgene and hydrogen chloride gases; both are toxic and irritating. /Dichlorobutene/
Melting Point · 3 items

-48 °C

Heat of Vaporization: 4.9201X10+7 J/kmol @ melting point

Surface Tension: 0.045796 Newtons/m @ melting point

Vapor Pressure

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H226 (98%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P320, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 2-Butene, 1,4-dichloro-, (Z)-

2-Butene, 1,4-dichloro-, (2Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Fire PotentialFlammable /Dichlorobutene/
Hazards Summary · 1 item

A skin, eye, and respiratory tract irritant; A lachrymator; May cause kidney, liver, and heart injury; [HSDB] Very toxic by inhalation and toxic by skin contact and ingestion; Causes burns; Inhalation may produce pneumonitis and pulmonary edema; [MSDSonline] See 1,4-Dichloro-2-butene.

Special Reports · 1 item

A REVIEW WITH 17 REFERENCES ON ACUTE TOXICITY OF CHLOROPRENE, 1,3-DICHLORO-2-BUTENE, & 1,4-DICHLORO-2-BUTENE. DATA INCL MUTAGENIC, SKIN, EYE & INHALATION TESTING, LETHAL, & TERATOGENIC DOSE VALUES.[CLARY JJ; ENVIRON HEALTH PERSPECT 21: 269-74 (1977)]

Flammable Limits1.5-4% /Dichlorobutene/

Chemistry & industry

Pharmacology

Metabolism/MetabolitesAN OXIDATION OF THE DOUBLE BOND IN CERTAIN HALO-OLEFINS, WHICH IS DEPENDENT ON MICROSOMAL MONO-OXYGENASES PROBABLY IS A COMMON PATHWAY IN THE FORMATION OF BIOLOGICALLY REACTIVE INTERMEDIATES.

Uses & manufacturing

Uses · 4 items

Intermediate for the production of other chemicals; [HSDB]

Dichloroprenes are used as nematocides and as intermediates in the manufacture of pesticides. /Dichloroprenes/

Occurs as an intermediate in the production of chloroprene...is a starting material in the production of adiponitrile, butane-1,4-diol, and tetrahydrofuran.

From 1951 to 1983 DuPont operated a butadiene chlorination process...the intermediate 1,4-dichloro-2-butene was converted to 3-hexenedinitrile...and then hydrogenated to adiponitrile

Methods of Manufacturing · 2 items

PREPARATION OF TRANS-1,4-DICHLOROBUTENE BY THE CHLORINATION OF BUTADIENE WAS FIRST REPORTED IN 1930, AND THIS METHOD IS USED FOR ITS COMMERCIAL PRODUCTION. THE ISOMERS 3,4-DICHLOROBUTENE, CIS-1,4-DICHLOROBUTENE & TRANS-1,4-DICHLOROBUTENE ARE PRODUCED, AND WHEN THE MIXTURE IS HEATED, AN EQUILIBRIUM RESULTS.

Obtained in a yield of 93% by chlorination of butadiene in the vapor phase at 300-350 °C...dichlorobutene isomers are also formed in the oxychlorination of C4 cracking fractions containing butadiene and isobutene /cis and trans-isomers/

Formulations/Preparations · 3 items

95% mixture of cis- and trans-isomers

98%: Cis-trans equilibrium mixture /Dichlorobutene/

1,4-DICHLOROBUTENE AVAILABLE IN USA CONTAINS 95-98% TRANS ... & 2-5% CIS ISOMER.

General Manufacturing Information2-Butene, 1,4-dichloro-, (2Z)-: ACTIVE
Applications · 1 item

Related reactions

140 records
New reaction record
HRID 55611 reaction equation
HRID 55611As reactantuspto-grants-1997_04
HRID 233175 reaction equation
HRID 233175As reactantuspto-grants-1997_01
HRID 233861 reaction equation
HRID 233861As reactantuspto-grants-1997_01
HRID 235404 reaction equation
HRID 235404As reactantuspto-grants-1997_01
HRID 264181 reaction equation
HRID 264181As reactantuspto-grants-1997_07
HRID 265494 reaction equation
HRID 265494As reactantuspto-grants-1997_07
HRID 266976 reaction equation
HRID 266976As reactantuspto-grants-1997_07
HRID 329264 reaction equation
HRID 329264As reactantuspto-grants-1977_04
Page 1 of 18

Compound notes

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· 2 items

4.09 [mmHg]

4.09 mm Hg @ 25 °C

Surface Tension24 dynes/cm = 0.024 N/m at 20 °C /Dichlorobutene/
Refractive IndexIndex of refraction: 1.4887 @ 25 °C/D

Physicochemical properties

Melting point
48 °C · −48 °C(lit.)
Boiling point
152 °C758 · 152 °C758 mm Hg(lit.)
Density
1.188 g/mL · 1.188 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.489(lit.)
Flash point
132 °F · 132 °F
storage temp.
2 · 2-8°C
solubility
Chlorform (Sparingly), Methanol (Slightly)
form
Liquid
color
Clear colorless to yellow
Water Solubility
Not miscible or difficult to mix in water. Soluble in alcohol, ether, acetone and benzene.
Sensitive
Moisture & Light Sensitive
BRN
1719692 · 1719692
Henry's Law Constant
3 · 3.0×10-2 mol/(m3Pa) at 25℃, Hiatt (2013)
Stability
Light Sensitive, Moisture Sensitive
CAS DataBase Reference
1476 · 1476-11-5(CAS DataBase Reference)
FDA UNII
2752 I90 · BQS2752I90
NIST Chemistry Reference
2 · 2-Butene, 1,4-dichloro-, (Z)-(1476-11-5)
EPA Substance Registry System
-1 · cis-1,4-Dichloro-2-butene (1476-11-5)
Symbol(GHS)
2 · GHS02,GHS05,GHS06,GHS08,GHS09
Signal word
Danger
Hazard statements
226 · H226-H301+H311-H314-H330-H350-H400
Precautionary statements
210 · P210-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazard Codes
T+,N
Risk Statements
45 · 45-24/25-26-34-50/53
Safety Statements
53 · 53-26-28-36/37/39-45-60-61
RIDADR
3390 · UN 3390 6.1/PG 1
WGK Germany
3 · 3
RTECS
4900000 · EM4900000
F
8 · 8-21
TSCA
TSCA listed
HazardClass
8 · 8
PackingGroup
I
HS Code
29032990 · 29032990
Hazardous Substances Data
1476 · 1476-11-5(Hazardous Substances Data)
Excepted Quantities
Forbidden
Hazard Classes and Categories
Flam. Liq. 3 (98%)
Explosive Limits and PotentialVapor may explode if ignited in an enclosed area. /Dichlorobutene/
Skin, Eye, and Respiratory Irritations · 3 items

... BOTH LIQUID AND VAPOR ARE HIGHLY DANGEROUS TO THE SKIN, EYES, LUNG, & INTERNAL ORGANS. /DICHLOROBUTENES/

Lacrimator

Inhalation of vapor irritates nose and throat. Contact with eyes causes intense irritation. /Dichlorobutene/

Critical Temperature and PressureCritical temp = 640 deg K; Critical pressure = 3.78X10+6 Pa

Safety & protection

Firefighting HazardsFlashback along vapor trail may occur. /Dichlorobutene/
Fire Fighting Procedures · 1 item

If material on fire or involved in fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. Use water spray to knock-down vapors. /Dichlorobutene/

Storage ConditionsStorage temperature: Ambient with open venting and equipped with a flame arrester. /Dichlorobutene/
Disposal Methods · 2 items

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.

/1,4-Dichloro-2-butene/ may be disposed of by the use of the following incineration methods: Rotary kiln with a temperature of 820-1600 °C and a residence time of seconds for liquids and gases, and hours for solids. Liquid injection with a temperature of 650-1600 °C with a residence time of 0.1-2 seconds. Fluidized bed with a temperature of 450-980 °C with a residence time of seconds for liquids and gases, longer for solids. /1,4-Dichloro-2-butene/

Preventive Measures · 4 items

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Dichlorobutene/

Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Dichlorobutene/

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.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Threshold Limit Values (TLV) · 3 items

8 hr Time Weighted Avg (TWA): 0.005 ppm, skin. /1,4-Dichloro-2-butene/

Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded. /1,4-Dichloro-2-butene/

A2; Suspected human carcinogen. /1,4-Dichloro-2-butene/

Personal Protective Equipment (PPE) · 3 items

Rubber gloves; chemical splash goggles; rubber boots & apron; barrier cream; organic canister mask. /Dichlorobutene/

Chemical protective clothing composed of polyvinyl alcohol (PVA), Viton (a proprietary fluoroelastomer), or Saranex (a multilayer laminate greater than 0.15 cm in thickness of polyethylene and Saran) is highly recommended, having break through times greater than one hour. Butyl rubber or polyethylene may be used but data suggest break through times of approximately an hour or more. Protective clothing composed of natural rubber, nitrile, chlorinated polyethylene, or polyvinyl chloride (material less than 0.015 cm thick) is not recommended since break through times were found to be significantly less than one hour. /1,4-Dichloro-2-butene/

Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. /Dichlorobutene/

Toxicology

Environmental Fate · 4 items

Aquatic Fate: Z-1,4-Dichloro-2-butene /hydrolysis/ yields 4-chloro-3-hydroxy-1-butene, E-1-chloro-4-hydroxy-1-butene, E-1-chloro-4-hydroxy-1-butene, and Z-1-chloro-4-hydroxy-1-butene.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 215(2) indicates that 1,4-dichloro-cis-2-butene is expected to have moderate mobility in soil(SRC). Volatilization of 1,4-dichloro-cis-2-butene from moist soil surfaces is expected to be an important fate process(SRC) given a an estimated Henry's Law constant of 1.2X10-3 atm-cu m/mole(SRC), based upon its vapor pressure, 4.09 mm Hg(3), and water solubility, 580 mg/l(4). The potential for volatilization of 1,4-dichloro-cis-2-butene from dry soil surfaces may exist(SRC) based upon its vapor pressure(3). In a soil degradation study, approximately 5-15% of initially added 1,4-dichloro-cis-2-butene was recovered in gas-traps after a 7-day period indicating soil volatilization had occurred(2). Soil degradation studies conducted over a one week incubation period in a sandy loam and silt loam soils found degradation half-lives of 1.8 to 2.5 days in both sterile and non-sterile soils(2); degradation rates in non-sterile soils were not significantly faster than in sterile soils indicating that abiotic or evaporative processes were more important than biological processes for 1,4-dichloro-cis-2-butene(2,5). The hydrolysis half-life of 1,4-dichloro-cis-2-butene was measured as 3.2 days under neutral conditions(6), suggesting hydrolysis may be an important fate process in moist soils.

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 215(SRC), indicates that 1,4-dichloro-cis-2-butene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-3 atm-cu m/mole(SRC), based upon its vapor pressure, 4.09 mm Hg(4), and water solubility, 580 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hours and 5 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 17(SRC), from its water solubility(5) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low. The hydrolysis half-life of 1,4-dichloro-cis-2-butene was measured as 3.2 days under neutral conditions(7). Limited soil data suggest that biodegradation will not be an important fate process in water since volatilization and hydrolysis are expected to occur rapidly(2,8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-dichloro-cis-2-butene, which has a vapor pressure of 4.09 mm Hg at 25 °C(1) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-dichloro-cis-2-butene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC). The half-life for the reaction in air with hydroxyl radicals is estimated to be 12 hours(SRC), calculated from its rate constants of 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(3). The half-life for the reaction in air with ozone is estimated to be 16 days(SRC), calculated from its rate constants of 7.1X10-19 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(3).

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.
Soil Adsorption/Mobility · 1 item

Using sandy loam and silt loam soils, the Koc of 1,4-dichloro-cis-2-butene was experimentally determined to be 215(1). According to a classification scheme(2), this Koc value suggests that 1,4-dichloro-cis-2-butene will have moderate mobility in soil(SRC).

Human Toxicity Excerpts · 3 items

Inhalation of vapor irritates nose and throat. Contact with eyes causes intense irritation and tears. Contact of liquid with skin causes severe blistering and dermatitis. Ingestion causes severe irritation of the mouth and stomach. /Dichlorobutene/

... BOTH LIQUID AND VAPOR ARE HIGHLY DANGEROUS TO THE SKIN, EYES, LUNG, & INTERNAL ORGANS. /DICHLOROBUTENES/

Symptomatology: 1A) Inhalation, high vapor concn: gasping, refusal to breathe, coughing, substernal pain, & extreme respiratory distress at vapor concn over 1500 ppm. Irritation of eyes & upper respiratory mucosa appears promptly after exposure to concentrated vapors. Lacrimation & headache are prominent. Coma may occur rapidly. B) Inhalation, low vapor concn: central nervous depression & moderate irritation of respiratory system. Headache is frequent. 2) Dermal: severe skin irritation with marked inflammatory response of epidermis & underlying tissues. 3) Oral: acute gastrointestinal distress with pulmonary congestion & edema. Central nervous depression, perhaps even in the absence of impaired oxygen uptake. 4) By any route, possible late injuries to liver, kidneys & heart. 5) After inhalation exposures, malaise, headache, chest & abdominal discomfort & irritability have been reported to persist for several weeks & perhaps for several years.

Artificial Pollution Sources · 1 item

1,4-Dichloro-cis-2-butene's production and use as a starting material in the manufacture of adiponitrile, butane-1,4-diol and tetrahydrofuran(1) may result in its release to the environment through various waste streams(SRC). It also occurs as an intermediate in the production of chloroprene(1).

Environmental Biodegradation · 1 item

Soil degradation studies conducted with 1,4-dichloro-cis-2-butene over a one week incubation period in a sandy loam and silt loam soils found degradation half-lives of 1.8 to 2.5 days in both sterile and non-sterile soils(1); degradation rates in non-sterile soils were not significantly faster than in sterile soils indicating that abiotic or evaporative processes were more important than biological processes for 1,4-dichloro-cis-2-butene(1,2).

Environmental Bioconcentration · 1 item

An estimated BCF of 17 was calculated for 1,4-dichloro-cis-2-butene(SRC), using a water solubility of 580 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 1,4-dichloro-cis-2-butene is estimated as 1.2X10-3 atm-cu m/mole(SRC) based upon its vapor pressure, 4.09 mm Hg(1), and water solubility, 580 mg/l(2). This Henry's Law constant indicates that 1,4-dichloro-cis-2-butene is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 5 days(SRC). 1,4-Dichloro-cis-2-butene's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1,4-dichloro-cis-2-butene from dry soil surfaces may exist(SRC) based upon the vapor pressure of this compound(1). In a soil degradation study, approximately 5-15% of initially added 1,4-dichloro-cis-2-butene was recovered in gas-traps after a 7-day period suggesting volatilization will be important(4).

Evidence for CarcinogenicityA2; Suspected human carcinogen. /1,4-Dichloro-2-butene/
Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 1,4-dichloro-cis-2-butene with photochemically-produced hydroxyl radicals has been estimated as 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 1,4-dichloro-cis-2-butene with ozone has been estimated as 7.1X10-19 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). The neutral hydrolysis rate constant of 1,4-dichloro-cis-2-butene has been experimentally determined to be 0.0090/hr at 25 °C which corresponds to a half-life of 3.2 days(3).

Probable Routes of Human ExposureOccupational exposure to 1,4-dichloro-cis-2-butene may occur through inhalation and dermal contact with this compound at workplaces where 1,4-dichloro-cis-2-butene is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 item

1,4-Dichloro-cis-2-butene's production and use as a starting material in the manufacture of adiponitrile, butane-1,4-diol and tetrahydrofuran may result in its release to the environment through various waste streams. It also occurs as an intermediate in the production of chloroprene. If released to air, a vapor pressure of 4.09 mm Hg at 25 °C indicates 1,4-dichloro-cis-2-butene will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-dichloro-cis-2-butene will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules. The half-life for the reaction in air with hydroxyl radicals is estimated to be 12 hours and the reaction with ozone molecules is about 16 days. If released to soil, 1,4-dichloro-cis-2-butene is expected to have moderate mobility based upon a Koc of 215. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1.2X10-3 atm-cu m/mole. 1,4-Dichloro-cis-2-butene may volatilize from dry soil surfaces based upon its vapor pressure. The hydrolysis half-life of 1,4-dichloro-cis-2-butene was measured as 3.2 days under neutral conditions, suggesting hydrolysis may be an important fate process in moist soils and water. Limited soil data suggest that biodegradation may occur, but will not be an important fate process since volatilization and hydrolysis are expected to occur rapidly. If released into water, 1,4-dichloro-cis-2-butene is not expected to adsorb to suspended solids and sediment based upon the Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 2 hours and 5 days, respectively. An estimated BCF of 17 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to 1,4-dichloro-cis-2-butene may occur through inhalation and dermal contact with this compound at workplaces where 1,4-dichloro-cis-2-butene is produced or used. (SRC)

Safety data

F
8-21
wgk
3
tsca
TSCA listed
rtecs
EM4900000
ridadr
UN 3390 6.1/PG 1
hs_code
29032990
risk_code
45-24/25-26-34-50/53
Signal word
Danger
Symbol(GHS)
GHS02,GHS05,GHS06,GHS08,GHS09
hazard_code
T+,N
safety_code
53-26-28-36/37/39-45-60-61
hazard_class
8
packing_group
I
Hazard statements
H226-H301+H311-H314-H330-H350-H400
Excepted Quantities
Forbidden
Precautionary statements
P210-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazardous Substances Data
1476-11-5(Hazardous Substances Data)

UsesIt is employed as an intermediate for the production of other chemicals such as in the production of chloroprene. It is also used as a starting material in the production of adiponitrile, butane-1,4-diol, and tetrahydrofuran. It is also used in the preparation of functionalized 3,5-disubstituted cyclopent-2-enones.

Upstream & downstream products

Upstream raw materials

cis-2-Butene-1,4-diolDiethyl etherPyridineThionyl chloride2,5-Dihydrofuran1,4-Dichloro-2-butynetrans-1,4-Dichloro-2-buteneCyclohexene1,3-Butadiene

Downstream products

Methyl 3-cyclopentenecarboxylate1,4-Butanediol2-chloro-1,3-butadieneTetrahydrofuranCinnamyl chloride2-Buten-1-amine, 4-chloro-DL-1,4-Dichloro-2,3-butanediolcis-N-(4-Chlorobutenyl)phthalimide