顺式-1,4-二氯-2-丁烯

1,4-Dichloro-2-butene

HCID 15122CAS 1476-11-5

基本信息

标准SMILES
ClCC=CCCl
InChIKey
FQDIANVAWVHZIR-UHFFFAOYSA-N
分子式
C4H6Cl2
平均分子量
124.99 g/mol
单同位素质量
123.98465555

概述

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

名称与标识

首选名称
1,4-Dichloro-2-butene
IUPAC
1,4-dichlorobut-2-ene
中文名
顺式-1,4-二氯-2-丁烯
英文名
cis-1,4-Dichloro-2-butene
分子式
C4H6Cl2
分子量
125

名称与别名

1,4-Dichlorobut-2-ene1,4-DICHLORO-2-BUTENE764-41-0DTXSID90273102-Butene, 1,4-dichloro-2-Butylene dichloride1,4-Dichloro-2-butyleneDTXCID4028123RefChem:416736212-121-81,4-DCB1,4-Dichlorobutene-2
展开更多名称
二氯丁烯吡哆醇杂质6吡哆素杂质6顺-1,4-二氯丁烯顺式-1,4-二氯丁烯顺-1,4-二氯-2-丁烯顺式-1,4-二氯-2-丁烯顺式-1-4-二氯-2-丁烯(Z)-1,4-二氯丁-2-烯1,4-二氯-2-丁烯(顺式)(Z)-1,4-dichlorobut-2-eneoro-2-butenecis-1,4-DichLcis-1,4-Dichloro-2-bPyridoxine Impurity 61,4-Dichlor-2-butencis(Z)-1,4-DichlorobuteneCIS-1,4-DICHLOROBUTENE4-dichloro-(z)-2-buten4-dichloro-cis-2-buten
1476-11-51,4-Dichloro-2-butene (cis+trans)ClCH2CH=CHCH2Cl1,4-Dichlorobutene-2 (65% trans-, 35% cis-)1,4-Dichloro-but-2-eneSCHEMBL205123CHEMBL3182125AKOS025243623

数据库标识

CAS
1476-11-5、764-41-0
PubChem CID
15122
DTXSID
DTXSID9027310
ChEMBL
CHEMBL3182125
EC Number
212-121-8

性质

结构计算性质

XLogP
1.7
极性表面积
0 Ų
氢键供体
0
氢键受体
0
可旋转键
2
重原子
6

实验与物化性质

Chemical ClassesOther Classes -> Halogenated Aliphatics, Unsaturated
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
OdorSweet, pungent
Density · 4 条

1.112 at 68 °F (USCG, 1999) - Denser than water; will sink

1.1858

Density: 1.183 (technical grade mixture) of cis and trans isomers.

1.185 No temp

Color/FormColorless liquid
Solubility · 3 条

Miscible with benzene, alc, carbon tetrachloride; immiscible with ethylene glycol and glycerol.

Soluble in ether.

Water solubility = 580 mg/l at 25 °C

物理化学性质

熔点
48 °C · −48 °C(lit.)
沸点
152 °C758 · 152 °C758 mm Hg(lit.)
密度
1.188 g/mL · 1.188 g/mL at 25 °C(lit.)
折射率
20 · n20/D 1.489(lit.)
闪点
132 °F · 132 °F
储存条件
2 · 2-8°C

化学性质

液体。熔点-48℃,沸点152℃ /101kPa。相对密度 1.88,折光率1.4884。

安全与法规

GHS分类

GHS Classification · 6 条

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

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

Danger

H226 (47.5%): 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)

危害信息

Regulatory Information · 5 条

Chemical: 2-Butene, 1,4-dichloro-

Hazard Traits - Carcinogenicity

2-Butene, 1,4-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butene, 1,4-dichloro- 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)

2-Butylene dichloride: HSNO Approval: HSR002956 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 2-Butene, 1,4-dichloro-: Environment tier I assessment
DOT LabelCorrosive Flammable Liquid
Fire HazardsSpecial Hazards of Combustion Products: Decomposition vapors contain phosgene and hydrogen chloride gases; both are toxic and irritating. (USCG, 1999)
Health HazardsInhalation 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 mouth and stomach. (USCG, 1999)
Hazards Summary · 1 条

Highly toxic; [Quick CPC] When heated, decomposes to toxic gases: phosgene and HCl; High inhalation exposure can cause pulmonary edema; [HSDB] Skin contact with liquid causes severe blistering; [CHRIS] Induces genetic damage in germ cells of humans or animals (3A); [MAK] Reacts with water forming hydrochloric acid; Vapor is irritating to nose and throat; Highly irritating to skin (blistering) and eyes (lachrymation); [CAMEO] Generally available in the US as a mixture of 95-98% trans- (CAS# 110-57-6) and 2-5% cis- (CAS#1476-11-5) isomers; [OECD SIDS] Causes burns and lachrymation; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Highly toxic by inhalation; Toxic by ingestion and skin absorption; [Aldrich MSDS] See 1,4-Dichloro-trans-2-butene.

安全与防护

Fire FightingExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
First AidINHALATION: remove from exposure; provide low-pressure oxygen if required; keep under observation until edema is ruled out.
Firefighting HazardsIf fire becomes uncontrollable or container is exposed to direct flame- evacuate for a radius of 1500 ft. If material leaking (not on fire), downwind evacuation must be considered. /Dichlorobutene, flammable liquid, corrosive/
Fire Fighting Procedures · 2 条

When fighting fires wear goggles and self-contained breathing apparatus. Extinguish with water, dry chemicals, foam, or carbon dioxide. /Dichlorobutene/

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 /Dichlorobutene/
Nonfire Spill ResponseExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

毒理信息

Ecotoxicity ValuesLD50 Poecilia reticulata (Guppy) << 40 mg/l/7 day
Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 215(2) indicates that 1,4-dichloro-2-butene is expected to have moderate mobility in soil(SRC). Volatilization of 1,4-dichloro-2-butene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 3 mm Hg(3), and water solubility, 580 mg/l(3). The potential for volatilization of 1,4-dichloro-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-2-butene was recovered in gas-traps after a 7-day period indicating soil volatilization had occurred(2). Soil degradation studies conducted over a 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-2-butene (cis-isomer)(2,4). The hydrolysis half-life of 1,4-dichloro-2-butene was measured as 3.2 days under neutral conditions(5), 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-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 5.8X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 3 mm Hg(4), and water solubility, 580 mg/l(4). 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(5), an estimated BCF of 14(SRC), from its water solubility(4) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low. The hydrolysis half-life of 1,4-dichloro-2-butene was measured as 3.2 days under neutral conditions(6). Limited soil data suggest that biodegradation will not be an important fate process in water since volatilization and hydrolysis are expected to occur rapidly(2,7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-dichloro-2-butene, which has a vapor pressure of 3 mm Hg at 25 °C(1) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-dichloro-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 is estimated to be 12 hours for the cis isomer and about 10 hours for the trans isomer(SRC), calculated from its rate constants of 3.3X10-11 cu cm/molecule-sec and 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) for the cis and trans isomers, respectively, using a structure estimation method(3). The half-life for the reaction with ozone is estimated to be 16 days for the cis isomer and about 8 days for the trans isomer(SRC), calculated from its rate constants of 7.1X10-19 cu cm/molecule-sec and 1.4X10-18 cu cm/molecule-sec at 25 °C(SRC) for the cis and trans isomers, respectively, using a structure estimation method(3).

Adverse EffectsDermatotoxin - Skin burns.
Soil Adsorption/Mobility · 1 条

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

TSCA Test Submissions · 2 条

Chronic toxicity and oncogenicity were evaluated in male Crl:CD(SD)BR rats exposed to 1,4-dichloro-2-butene (DCB) via inhalation at concentrations of (number of rats): 0 (160), 0.10 (150), 0.31 (150) or 1.0 ppm (128) for 6 hrs/day, 5 days/week for 3-19 months with rats surviving 19 months of exposure held without treatment for an additional 5 months. All groups exhibited infection by Corynebacterium kutscheri which especially affected the chronic toxicity portion of the tests. After adjusting for effects due to the infection, there was a statistical increase in mortality in the high dose group. There were significant dose-related increases in treated groups relative to controls in various nasal tumors (dose group(ppm)/month first observed): benign tumors in the respiratory region of the nasal cavity (1.0/10 months, 0.31/12 months, 0.10/19 months), and malignant tumors in the olfactory region (1.0/12 months, 0.31/19 months). The increase in tumor incidence was statistically significant at all exposure concentrations for benign tumors, at 1.0 ppm for malignant tumors and at 0.3 and 1.0 ppm for both types of tumors combined. The infection did not appear to affect tumor incidence although the infection reduced the numbers of rats at risk due to an increased mortality.

Chronic toxicity and oncogenicity were evaluated in male and female Charles River Chr:CD rats (140/sex/group) exposed to 1,4-dichloro-2-butene (DCB) via inhalation at concentrations of 0, 0.5 for 6 hrs/day, 5 days/week for 2 yrs or at 5.0 ppm for 7 months followed by 2.5 ppm for 17 months (reduced due to excessive body weight loss and respiratory difficulty). There were significant dose-related differences between high-dose level and control animals of both sexes in the following: body weights and mortality (decreased and increased respectively), poorly differentiated and highly invasive nasal carcinomas and tracheal epithelial metaplasia (increased at 1 yr sacrifice), benign nasal adenomas (at 18 months), and primarily malignant nasal tumors, many of which metastasized to the cervical lymph nodes and lungs, including adenomas/carcinomas, squamous cell carcinomas, mixed carcinomas, rhabdomyosarcomas, and carcinosarcomas and a few benign nasal tumors (at 2 yrs). Pulmonary squamous cell carcinomas were observed in 3 high-dose males. Greater incidences of benign adenomas or hemangiomas and malignant tumors were observed in both sexes at low-dose level. Also observed in high-dose level animals were increases in the following: rhinitis, tracheal luminal exudate, atelectasis, suppurative pneumonia, and hyperplasia of the bone marrow (statistical significance not reported).

Human Toxicity Excerpts · 5 条

PROTRACTED CONTACT WITH SKIN CAUSES DERMATITIS AND BLISTERING. HIGH CONCN OF VAPOR APPARENTLY HAVE DELAYED TOXIC EFFECT ON EYES, CAUSING ONSET OF IRRITATION AND LACRIMATION SEVERAL HR AFTER THE EXPOSURE, SEEMING SIMILAR TO DIMETHYL SULFATE AND OTHER ALKYLATING AGENTS IN MODE OF ACTION.

IRRITANT TO SKIN ... CAUSES BLISTERS.

HIGH CONCN OF VAPOR APPARENTLY HAVE DELAYED TOXIC EFFECT ON EYES, CAUSING ONSET OF IRRITATION & LACRIMATION SEVERAL HOURS AFTER EXPOSURE ...

... BOTH LIQ AND VAPOR ARE HIGHLY /IRRITATING AND TOXIC/ TO THE SKIN, EYES, LUNG, & INTERNAL ORGANS.

For more Human Toxicity Excerpts (Complete) data for 1,4-DICHLORO-2-BUTENE (6 total), please visit the HSDB record page.

法规信息

RCRA Requirements · 1 条

U074; As stipulated in 40 CFR 261.33, when 1,4-dichloro-2-butene, 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).

CERCLA Reportable Quantities · 1 条

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 1 lb or .454 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).

安全数据

F
8-21
wgk
3
tsca
TSCA listed
RTECS号
EM4900000
包装类别
I
危险等级
8

化学与工业

药理信息

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.

用途与制造

Uses · 5 条

Used as an intermediate in chemical manufacturing; [HSDB] Continuously manufactured and processed in closed systems and essentially used 100% as an intermediate; [OECD SIDS]

CHEM INT FOR 3,4-DICHLORO-1-BUTENE (A CHLOROPRENE INT), ADIPONITRILE (A HEXAMETHYLENEDIAMINE INT) & CHEM INT FOR 1,4-BUTANEDIOL (NON-US USE).

1,4-Dichloro-2-butene is used for resolving oil-in-water emulsions.

Used 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.

U.S. Production · 3 条

2023: 2,700,000 lb

(1977) AT LEAST 4.54X10+9 G

(1982) PROBABLY GREATER THAN 4.54X10+6 G

Consumption PatternsESSENTIALLY 100% AS A CHEM INT FOR 3,4-DICHLORO-1-BUTENE & ADIPONITRILE
Industry UsesMonomers
Methods of Manufacturing · 3 条

The isomers 3,4-dichlorobutene, cis-1,4-dichlorobutene & trans-1,4-dichlorobutene are produced /by the reaction of chlorine & butadiene/, & when the mixture is heated, an equilibrium results. The residue resulting from removal of the 3,4-isomer ... is normally used without further separation.

Chlorination of butadiene in chloroform or carbon disulfide below 0 °C gives a mixture of 3,4-dichloro-1-butene and 1,4-dichloro-2-butene, in a ratio of about 2:1

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. /Dichlorobutene isomers/

Formulations/Preparations · 2 条

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

1,4-Dichlorobutene, technical grade, 85%, is a mixture of both cis- and trans- isomers.

应用领域

用途吡咯芬的合成。

制备方法

生产方法用丁烯二醇以氯化亚硫酰氯化制得。

试剂价格

D2449 · 5G
顺-1,4-二氯-2-丁烯cis-1,4-Dichloro-2-butene — 40元
D2449 · 25G
顺-1,4-二氯-2-丁烯cis-1,4-Dichloro-2-butene — 160元

供应商50 家

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]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
邹平创新药业有限公司13561560789 · [email protected]

相关反应

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