1,1,2-Trichloroethane

HCID 6574CAS 79-00-5

基本情報

標準SMILES
ClCC(Cl)Cl
InChIKey
UBOXGVDOUJQMTN-UHFFFAOYSA-N
分子式
C2H3Cl3
平均分子量
133.4 g/mol
単同位体質量
131.93003314

概要

1,1,2-Trichloroethane is a colorless, sweet-smelling liquid. It does not burn easily, can be dissolved in water, and evaporates easily. It is used as a solvent (a chemical that dissolves other substances) and as an intermediate in the production of the chemical, 1,1-dichloroethane. 1,1,2-Trichloroethane is sometimes present as an impurity in other chemicals, and it may be formed when another chemical breaks down in the environment under conditions where there is no air.

名称と識別子

優先名称
1,1,2-Trichloroethane
IUPAC
1,1,2-trichloroethane
現地名
1,1,2-トリクロロエタン
英語名
1,1,2-Trichloroethane
分子式
C2H3Cl3
分子量
133.4

名称と別名

1,1,2-TRICHLOROETHANE79-00-5VinyltrichlorideEthane, 1,1,2-trichloro-beta-TrichloroethaneVinyl trichloride1,1,2-TrichlorethaneEthane trichloridebeta-TNCI-C04579Caswell No. 875ADTXSID5021380
名称をさらに表示
1,1,2-トリクロロエタン1,1,2-トリクロロエタン (1mg/mlメタノール溶液) [水質分析用]ビニルトリクロリドエタントリクロリドβ-トリクロロエタン1,2,2-トリクロロエタン1,1,2-トリクロロエタン標準原液1,1,2トリクロロエタン1,1,2‐トリクロロエタン1,1,2‐トリクロロエタン標準原液1,1,2-トリクロロエタン STANDARD1,1,2-トリクロロエタン 溶液1,1,2-トリクロロエタン Standard, 2.0 mg/mL in MeOH1,1,2-トリクロロエタン, 0.2 mg/mL in MeOH1,1,2-トリクロロエタン, 100 µg/mL in MeOH1,1,2-tce1,1,2-Trichlorethan1,2,2-TrichloroethaneEthane,1,1,2-trichloro-1,1,2-Trichloroethane,98%R-140freon140CHCl2CH2Cl
Trojchloroetan(1,1,2)Trichloroethane, 1,1,2-1,1,2-Trichloraethan28E9ERN9WUEPA Pesticide Chemical Code 081203BRN 1731726NSC-405074CHEBI:36018

データベース識別子

CAS
79-00-5
PubChem CID
6574
DTXSID
DTXSID5021380
ChEBI
CHEBI:36018
UNII
28E9ERN9WU
EC Number
201-166-9
Nikkaji
J1.962C

物性

構造計算による物性

XLogP
1.9
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
1
重原子数
5

実験および物理化学的性質

Chemical Classes · 3 件

Hazardous Air Pollutants (HAPs)

Carcinogens

Volatile Organic Compound (VOC)

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

log Kow = 1.89

2.35

Odor · 2 件

Pleasant odor

Sweet chloroform-like odor

物理化学的性質

融点
-37 °C · -37 °C
沸点
110 · 110-115 °C (lit.)
比重(密度)
1.435 g/mL · 1.435 g/mL at 25 °C (lit.)
蒸気圧
30.3 at · 30.3 at 25 °C (quoted, Mackay et al., 1982)
屈折率
20 · n20/D 1.471(lit.)
闪点
11 °C · 11 °C

化学的性質

化学的特性1,1,2-Trichloroethane is a colorless, nonflammable (must be pre-heated before ignition can occur) liquid Sweet, chloroform-like odor.

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Danger

H302+H312+H332 (30.4%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P316, P317, P318, P321, P330, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Ethane, 1,1,2-trichloro-

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

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

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

Status: Active Update: 12-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/1878

Restricted substance: 1,1,2-Trichloroethane

Other Safety InformationIMAP assessments - Ethane, 1,1,2-trichloro-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 件

Special Hazards of Combustion Products: Toxic gases including hydrogen chloride and very small amounts of phosgene and chlorine are produced.

Combustible under specific conditions. Heating will cause rise in pressure with risk of bursting.

Fire PotentialNonflammable /liquid/
Health Hazards · 1 件

Inhalation causes irritation of the nose, throat, and lungs. High concentrations may cause death by respiratory failure. Highly toxic by ingestion; may cause liver or kidney damage or myocardial irritability. Causes severe irritation of the gastrointestinal tract. Vapor may produce superficial skin burns or defatting type dermatitis and may irritate the eyes. (USCG, 1999)

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

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

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

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

Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Refer for medical attention . Do NOT induce vomiting.

First Aid · 2 件

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 procedures)

Safe StorageSeparated from strong oxidants, strong bases and metals. Well closed. Ventilation along the floor. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
Exposure Control and Personal Protection10.0 [ppm]
Fire Fighting Procedures · 2 件

Wear special protective clothing and positive pressure self-contained breathing apparatus.

Extinguish fire using agent suitable for surrounding fire. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.

毒性情報

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1 件

1,1,2-Trichloroethane was not detected in any human adipose sample analyzed as part of the USEPA NHATS study for fiscal year 1982(1). The breath of 9 human subjects from NJ was found to contain a median 1,1,2-trichloroethane conc of 0.2 ug/cu m(2); the median background conc in ambient air was 2.8 ug/cu m(2). 1,1,2-Trichloroethane was identified, not quantified, in samples of blood obtained in October 2001 from firefighters that responded to the collapse of the World Trade Center(3).

Treatment · 1 件

Following ingestion, administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old. Consider gastric lavage after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion. In case of seizures, administer a benzodiazepine IV. 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 eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. (T36)

Cancer Sites · 2 件

Hepatic

[in animals: liver cancer]

Interactions · 3 件

Acetone potentiation of 1,1,2-trichloroethane hepatotoxicity was found to be strongly dose-dependent for both acetone and 1,1,2-trichloroethane. An oral dose of 0.5 ml of acetone/kg was the most effective potentiating pretreatment when administered 16 hr prior to 1,1,2-trichloroethane. Surprisingly, higher doses of acetone did not potentiate the hepatotoxicity of 1,1,2-trichloroethane, but may have decreased the severity of this toxicity. Acetone potentiation of hepatotoxicity was most pronounced at or near the hepatotoxic threshold for 1,1,2-trichloroethane. While acetone treatment alone did not affect hepatic glutathione (GSH) stores the most consistent effect produced by acetone pretreatment was a significant potentiation of 1,1,2-trichloroethane-induced depletion of hepatic GSH. These findings suggest that critical doses of acetone may enhance the subsequent hepatotoxicity of 1,1,2-trichloroethane via mechanisms that affect the interaction of 1,1,2-trichloroethane and hepatic GSH stores.

Mice pretreated with isopropanol (2.5 ml/kg) by gavage showed an increased hepatotoxic response to threshold doses of 1,1,2-trichloroethane as measured by serum glutamic-pyruvic transaminase activity.

Polybrominated biphenyls (PBBs) were shown to increase the renal toxicity of 1,1,2-trichloroethane as measured by decreases in para-aminohippurate accumulation in renal cortical slices. PBBs are known to increase the activities of microsomal mixed-function oxygenases in the kidney and liver, so increased metabolism of 1,1,2- trichloroethane and the increased presence of metabolites more toxic than the parent compound itself may be responsible for the increased toxicity of 1,1,2-trichloroethane in the kidney. However, the study also showed that PBBs did not increase the hepatotoxic effects of 1,1,2-trichloroethane, as indicated by relative liver weight or SGOT levels.

Target Organs · 3 件

Hepatic (Liver), Immunological (Immune System), Neurological (Nervous System), Respiratory (From the Nose to the Lungs)

Hematologic

Eyes, respiratory system, central nervous system, liver, kidneys

法規制情報

FDA Requirements1,1,2-Trichloroethane is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 2 件

U227; As stipulated in 40 CFR 261.33, when 1,1,2-trichloroethane 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).

F002; When 1,1,2-trichloroethane is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F002), as stated in 40 CFR 261.31, and must be managed according to state and/or federal hazardous waste regulations.

TSCA Requirements · 1 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethane, 1,1,2-trichloro- is included on this list.

Atmospheric Standards · 2 件

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. 1,1,2-Trichloroethane is produced, as an intermediate or 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. 1,1,2-Trichloroethane is included on this list.

CERCLA Reportable Quantities · 1 件

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 100 lb or 45.4 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 RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Chlorinated ethanes/

安全データ

OEB
A
OEL
TWA: 10 ppm (45 mg/m3) [skin] (Chloroethanes)
wgk
3
IDLA
100 ppm
tsca
TSCA listed
rtecs
KJ3150000

化学と産業

薬理情報

Biological Half-Life · 1 件

The half-life following 1 hour inhalation exposure to 1005 ppm of 1,1,2-trichloroethane in mice was determined to be 625 minutes in the heart, 203 minutes in the fat, 147 minutes in the brain, 127 minutes in the spleen, 122 minutes in the lungs, 43 minutes in the kidney, 39 minutes in the blood, and 19 minutes in the liver. The half-life in the whole body was calculated to be 49.3 minutes.

Metabolism/Metabolites · 5 件

1,1,2-Trichloroethane is extensively metabolized in mice given 100-200 mg/kg bw by intraperitoneal injection, 73-87% of the dose being eliminated in the urine and 16-22% in expired air. Several urinary metabolites have been identified: chloroacetic acid, S-carboxymethyl-L-cysteine, thiodiacetic acid, 2,2-dichloroethanol and oxalic acid.

The primary metabolites identified by high-performance liquid chromatography in rats and mice given 1,1,2-trichloroethane by gavage were chloroacetic acid, S-carboxymethylcysteine, and thiodiacetic acid.

Although percent of the orally-administered dose metabolized was identical in rats and mice (81%), the actual amount of 1,1,2-trichloroethane metabolized was much higher in mice. The chemical was given to each species at the MTD, which was 4.3 times greater in mice; mice experienced a higher body burden than rats, but were able to metabolize the same percentage of it. The inherent ability of mice to metabolize 1,1,2- trichloroethane at a higher rate than rats may contribute to the greater susceptibility of mice to 1,1,2-trichloroethance cytotoxicity and carcinogenity. It is not known how the rate of 1,1,2-trichloroethane metabolism in humans compares to that in mice and rats. Metabolism in humans is likely to be qualitatively similar to that in animals, however.

INCUBATION OF CHLOROETHANES, HEPATIC MICROSOMES, AN NADPH-GENERATING SYSTEM & EDTA RESULTS IN PRODUCTION OF CHLORINATED METABOLITES. ... MAJOR METABOLITE OF 1,1,2-TRICHLOROETHANE WAS DICHLOROACETATE.

After 1,1,2-trichloroethane enters the body, it is carried by the blood to organs and tissues such as the liver, kidney, brain, heart, spleen, and fat. The primary metabolites identified are chloroacetic acid, S-carboxymethylcysteine, and thiodiacetic acid. S-carboxymethycysteine and thiodiacetic acid are formed from 1,1,2-trichloroethane following conjugation with glutathione. Chloroacetic acid is formed by hepatic cytochrome P-450. This reaction is thought to proceed via the acyl chloride. Cytochrome P-450 can also produce free radicals from 1,1,2-trichloroethane. Experiments show that most 1,1,2-trichloroethane leaves the body unchanged in the breath and as other substances that it is changed into in the urine in about 1 day. (L422)

Absorption, Distribution and Excretion · 5 件

When (38)Cl-1,1,2-trichloroethane was administered by inhalation at a dose of about 5 mg per subject, about 3% of the compound was eliminated in the breath within 1 hr, and urinary excretion of (38)Cl amounted less than 0.01% of the dose/min.

Studies in humans indicate that 1,1,2-trichloroethane is absorbed rapidly after inhalation exposure. A volunteer took one breath of radiolabeled 1,1,2-trichloroethane and expired 10% of the inspired dose in the alveolar air after 12 seconds and about 0.5% after 40 seconds of breath-holding. More than 90% of the administered dose was retained in the body after 50 minutes. These data indicate that 1,1,2- trichloroethane was extensively absorbed into the bloodstream.

EXCRETION--RETENTION OF CHLORINATED ALIPHATIC CMPD IN MICE: 1,1,2-TRICHLOROETHANE EXCRETED 80% IN URINE, 1% IN FECES, 19% IN EXPIRED AIR, AND 2% RETENTION. /FROM TABLE/

In mice, 15 minutes after application of 0.5 ml of 1,1,2-trichloroethane, 99.7% was retained in the body and 0.3% was expired in the breath. The absorption rate was calculated to be 130 nmoles/min/sq cm of skin. The rapid absorption through the skin may well be due to the highly lipid soluble character of 1,1,2-trichloroethane.

For more Absorption, Distribution and Excretion (Complete) data for 1,1,2-TRICHLOROETHANE (15 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

1,1,2-Trichloroethane is primarily used as a chemical intermediate in the production of 1,1- dichloroethene. It is also used as a solvent for chlorinated rubbers, fats, oils, waxes, and resins.

Used primarily for synthesis of vinylidene chloride; also used as a solvent in pharmaceutical manufacturing; [ACGIH] Used in lacquers, adhesives, and resins; [HSDB] Used as a solvent for fats, waxes, natural resins, and alkaloids; [Merck Index]

Painting (Solvents) [Category: Paint]

Used in adhesives, production of Teflon tubing, in lacquer, and coating formulations.

Intermediate in the production of vinylidine chloride, as a solvent and component of adhesives.

Solvent for fats, oils, waxes, resins, other products; organic synthesis.

Impurities... 1,1,2-trichloroethane is available as a commercial grade product, either stablized or unstabilized, at a purity of >99%. The stabilized product contains sec-butanol (0.5%) and 1,2-butylene oxide (0.25%).
U.S. Production · 5 件

2023: 10,000,000 - <50,000,000 lb

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Data not available

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3136]

1,1,2-Trichloroethane 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).

Industry UsesIntermediate
Methods of Manufacturing · 3 件

PREPD BY CATALYTIC CHLORINATION OF ETHANE OR ETHYLENE.

... Reaction of acetylene gas with a mixture of hydrogen chloride and chlorine in the presence of catalyst or by chlorination of ethylene followed by chlorination of the 1,2-dichloroethane intermediate.

Industrial production of 1,1,2-trichloroethane proceeds by two routes: 1) selective chlorination of 1,2-dichloroethane and 2) addition of chlorine to vinyl chloride..

Formulations/Preparations · 2 件

In the USA, 1,1,2-trichloroethane is available as a commercial grade product, either stablized or unstabilized, at a purity of >99%. The stabilized product contains sec-butanol (0.5%) and 1,2-butylene oxide (0.25%).

Grade: Technical

応用分野 · 4 件

用途塩化ビニリデン原料,塩素化ゴム溶剤,油脂?ワックス?天然樹脂等溶剤,アルカロイド抽出剤,金属洗浄剤 (NITE CHRIP)

用途溶剤、抽出剤、有機合成原料、その他、燻蒸剤として用いられることもある。工業的には塩化ビニリデンの原料や洗浄剤、代替フロンの原料として使われる。

使用The use of 1,1,2-trichloroethane is quite restrictive. It is used to a slight extent as a specialty solvent and mostly as a chemical intermediate; a solvent for fats, waxes, natural resins, alkaloids, and various other organic materials; as an intermediate in production of vinylidene chloride and teflon tubing; and as a component of adhesives. The availability of other less toxic solvents discourages its use. More than 95% of this compound manufactured in the United States is consumed in producing vinylidene chloride. Domestic production is about 410 million pounds. It must not be confused with its much less toxic isomer, 1,1,1- trichloroethane.

一般的な説明A clear light colored liquid. Flash point between 0 and 74°F. Insoluble in water and slightly denser than water. Hence sinks in water. May be toxic by inhalation.

調製方法

純化方法Purify the chloroethane as for 1,1,1-trichloroethane above. [Beilstein 1 IV 139.]

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補足説明

定義ChEBI: A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1 and 2.

関連反応

59 件

関連ノート

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