3-氯丙烯

Allyl chloride

HCID 7850CAS 107-05-1

基本信息

标准SMILES
C=CCCl
InChIKey
OSDWBNJEKMUWAV-UHFFFAOYSA-N
分子式
C3H5Cl
平均分子量
76.52 g/mol
单同位素质量
76.00797784

概述

Allyl chloride appears as a clear colorless liquid with an unpleasant pungent odor. Flash point -20 °F. Boiling point 113 °F. Less dense than water (7.8 lb / gal) and insoluble in water. Hence floats on water. Vapor irritates skin, eyes and mucous membranes. Vapors are heavier than air. Long exposure to low concentrations or short exposure to high concentrations may have adverse health effects from inhalation or skin absorption.

名称与标识

首选名称
Allyl chloride
IUPAC
3-chloroprop-1-ene
英文名
1 -Chloro-2-propene
分子式
C3H5Cl
分子量
0

名称与别名

ALLYL CHLORIDE107-05-13-Chloro-1-propene3-Chloropropene1-Propene, 3-chloro-3-ChloropropyleneChlorallylene2-Propenyl chloride1-Chloro-2-propeneAllylchloridChloroallylene3-Chloropropene-1
展开更多名称
3-ChlorpropenPropene, 3-chloro-3-Chloro-1-propyleneChloro-2-propenealpha-ChloropropyleneNCI-C04615p-AminopropiofenonDTXSID4039231

数据库标识

CAS
107-05-1
PubChem CID
7850
DTXSID
DTXSID4039231
ChEMBL
CHEMBL451126
ChEBI
CHEBI:82379
UNII
V2RFT0R50S
EC Number
203-457-6
Nikkaji
J4.048G

性质

结构计算性质

XLogP
1.5
极性表面积
0 Ų
氢键供体
0
氢键受体
0
可旋转键
1
重原子
4

实验与物化性质

Chemical Classes · 3 条

Hazardous Air Pollutants (HAPs)

Carcinogens

Volatile Organic Compound (VOC)

SolventsSolvents -> Chlorinated Aliphatics
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
LogP · 2 条

2.1

3.0

OdorPungent, unpleasant odor.

物理化学性质

熔点
-135 °C · -135 °C
沸点
44 · 44-45 °C
密度
0.938 g/cm3 · 0.938 g/cm3

安全与法规

GHS分类

GHS Classification · 6 条

Danger

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

P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

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

P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

危害信息

Regulatory Information · 6 条

Chemical: 1-Propene, 3-chloro-

Hazard Traits - Neurotoxicity; Ocular Toxicity; Respiratory Toxicity

1-Propene, 3-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propene, 3-chloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14318

Allyl chloride: Does not have an individual approval but may be used under an appropriate group standard

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 - 1-propene, 3-chloro-: Human health tier II assessment
DOT LabelFlammable Liquid Poison
Fire Hazards · 3 条

Special Hazards of Combustion Products: Releases irritating hydrogen chloride gas on combustion (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers.

Fire PotentialDangerous fire and explosion hazard when exposed to heat or flame ...
Health Hazards · 2 条

Causes marked irritation of skin and may burn. Burns the eyes; effect may be delayed. (USCG, 1999)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

安全与防护

Fire Fighting · 2 条

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:

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

First Aid Measures · 4 条

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

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

Rinse mouth. Give a slurry of activated charcoal in water to drink. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2 条

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

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

First Aid · 3 条

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.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from food and feedstuffs and incompatible materials. See Chemical Dangers. Dry.
Firefighting HazardsVapor is heavier than air (vapor-air density at 100 °F, 2.2) and may travel considerable distance to source of ignition and flash back.

毒理信息

Target Organs · 2 条

Nervous

Eyes, skin, respiratory system, liver, kidneys

Ecotoxicity Values · 5 条

LC50 Poecilia reticulata (Guppy) 10 mg/L/24 hr, /Conditions of bioassay not specified in source examined/

LC50 Poecilia reticulata (Guppy) 57.68 mg/L/24 hr (95% confidence interval: 48.87-68.76 mg/L); static /formulated product/

LC50 Poecilia reticulata (Guppy) 53.54 mg/L/48 hr (95% confidence interval: 43.01-71.14 mg/L); static /formulated product/

LC50 Poecilia reticulata (Guppy) 51.08 mg/L/96 hr (95% confidence interval: 41.03-67.02 mg/L); static /formulated product/

For more Ecotoxicity Values (Complete) data for ALLYL CHLORIDE (18 total), please visit the HSDB record page.

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 51(SRC), determined from a water solubility of 3,370 mg/L(2) and a regression-derived equation(3), indicates that allyl chloride is expected to have high mobility in soil(SRC). Volatilization of allyl chloride from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.10X10-2 atm-cu m/mole(SRC), using a vapor pressure of 368 mm Hg(4), and water solubility of 337 mg/L(5). Allyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). A BOD of 62% in the Japanese MITI test(6) indicates that biodegradation is expected to be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 51(SRC), determined from a water solubility of 3,370 mg/L(2) and a regression-derived equation(3), indicates that allyl chloride 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 1.10X10-2 atm-cu m/ mol derived from it's vapor pressure, 368 mm Hg(4), and water solubility, 337 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 3 hours and 3 days, respectively(SRC). According to a classification scheme(6), a measured BCF range of <0.14 to <1.3(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Allyl chloride will undergo hydrolysis at pH=7 with a half-life of approximately 8 days(8). Based on a BOD of 62% in the Japanese MITI test(7), biodegradation is expected to be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), allyl chloride, which has a vapor pressure of 368 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase allyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 0.8 days(SRC), calculated from its rate constant of 1.70X10-11 cu cm/molecule-sec at 25 °C(3). Allyl chloride does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Sensorimotor
Exposure Routes · 2 条

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Ecotoxicity Excerpts · 1 条

/AQUATIC SPECIES/ The 14 day LC50 value of allyl chloride to the guppy (poecilia reticulata) was determined. These data were investigated through the construction of a quantitative structure-activity relationship. Both hydrophobicity and alkylating potency of the compound were found to be necessary parameters for the satisfactory description of the LC50 data. The log LC50 experimental data for allyl chloride was 1.20 umol/L as compared to the calculated quantitative structure-activity relationship value of 2.82 umol/L.

法规信息

Atmospheric Standards · 2 条

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

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Allyl chloride is included on this list.

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 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).

Clean Water Act Requirements · 1 条

Allyl chloride is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

State Drinking Water Guidelines · 3 条

(NH) NEW HAMPSHIRE 7.4 ug/L

(MN) MINNESOTA 30 ug/L

(FL) FLORIDA 35 ug/L

化学与工业

药理信息

Biological Half-LifeNo reports found; [TDR, p. 67]
Metabolism/Metabolites · 4 条

Allyl chloride ... dosed sc to male rats ... /was/ metabolized to allylmercapturic acid, S-allylcysteine, and S-allylcysteine S-oxide. 3-hydroxypropylmercapturic acid was /also/ a metabolite of allyl chloride ... .

Allyl glutathione and S-allyl-L-Cysteine have been detected in the bile of a rat given allyl chloride.

Allyl chloride is presumed to be metabolized to allyl alcohol, which could then be further metabolized via two pathways to form either acrolein or glycidol, from which a variety of metabolites could result. Metabolites identified in rat urine are 3-hydroxypropylmercapturic acid and allyl mercapturic acid and its sulfoxide. Allyl glutathione and S-allyl-L-cysteine have been detected in the bile of dosed rats. In-vitro metabolism of allyl chloride results in haem destruction in microsomal cytochrome P450.

...The biotransformation of allyl chloride (AC) in rats to select potential urinary biomarkers of exposure /was investigated/. ...The earlier described urinary metabolites of AC [allyl mercapturic acid (ALMA) and 3-hydroxypropyl mercapturic acid (HPMA)], as well as two urinary metabolites of ECH [alpha-chlorohydrin (alpha-CH) and 3-chloro-2-hydroxypropyl mercapturic acid (CHPMA)], were determined in this study. After ip administration of AC, in doses ranging from 66 to 590 umol/kg, control rats excreted 30 +/- 6.5% of the AC dose as ALMA. HPMA was a minor urinary metabolite of AC (<3% of the AC dose), and, for this metabolite, no clear dose-excretion relationship was found. Two other minor urinary metabolites were also found as well, namely CHPMA and alpha-CH, suggesting the formation of ECH. CHPMA excretion was linear from 66 to 330 umol/kg AC and amounted to 0.21 +/- 0.08% of the AC dose. alpha-CH excretion was linear in the dose range used and was excreted for 0.13 +/- 0.02% of the AC dose. In addition, we investigated the influence of three different enzyme inducers on the urinary metabolite profile of AC, namely pyrazole, beta-naphthoflavone, and phenobarbital. Pyrazole only increased the urinary excretion of alpha-CH. beta-Naphthoflavone induction only enhanced the ALMA excretion significantly. Phenobarbital inducted both the excretion of CHPMA and alpha-CH.

用途与制造

Uses · 6 条

Almost all of the allyl chloride produced is used to make epichlorohydrin and glycerin. Allyl chloride derivatives are found in varnish, plastics, adhesives, perfumes, pharmaceuticals, and insecticides.

Used in the manufacture of organic chemicals; [ACGIH] Used to make glycerin and epoxy resin; [Rosenstock, p. 676]

In the synthesis of allyl compounds.

Synthesis of intermediates for manufacture of polymers, resins, & plastics

Thermosetting resins for varnishes, plastics, adhesives; synthesis of pharmaceuticals & insecticides.

Chemical intermediate for diuretics

U.S. Production · 6 条

2023: 100,000,000 - <500,000,000 lb

1-Propene, 3-chloro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Data not published.

(1986) > 500 million - 1 billion pounds

(1990) > 500 million - 1 billion pounds

For more U.S. Production (Complete) data for ALLYL CHLORIDE (9 total), please visit the HSDB record page.

Consumption PatternsPrimarily as a chemical intermediate for epichlorohydrin
Industry UsesMonomers
Methods of Manufacturing · 3 条

Allyl chloride is produced on a large scale by the high-temperature (300-600 °C) chlorination of propene ... At these temperatures, chlorination proceeds by a free-radical chain mechanism, whereby the hydrogen atom in the allyl position is substituted preferentially by the chlorine, giving allyl chloride

Manufactured by chlorination of propylene; Samples, Hilbert, US 3054831 (1962 to Union Carbide).

First prepared by the reaction of allyl alcohol with phosphorous chloride

Formulations/PreparationsDry & liquid grades

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相关反应

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