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Bromotrichloromethane

HCID 6383
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
75-62-7
표준 SMILES
ClC(Cl)(Cl)Br
InChIKey
XNNQFQFUQLJSQT-UHFFFAOYSA-N
분자식
CBrCl3
평균 분자량
198.27 g/mol
단동위원소 질량
195.8249

개요

A potent liver poison. In rats, bromotrichloromethane produces about three times the degree of liver microsomal lipid peroxidation as does carbon tetrachloride.

이름 및 식별자

우선 이름
Bromotrichloromethane
IUPAC
bromo(trichloro)methane
영어명
Bromotrichloro methane
분자식
CBrCl3
분자량
198.2737

이름 및 동의어

BROMOTRICHLOROMETHANE75-62-7TrichlorobromomethaneMethane, bromotrichloro-Carbon bromotrichlorideMonobromotrichloromethaneCarbon trichlorobromideTrichloromethyl bromideDTXSID7023930IKJ30QXM63NSC-8017DTXCID003930
이름 더 보기
RefChem:121643200-886-0bromo(trichloro)methaneCBrCl3bromotrichloro methaneCaswell No. 118CCl3BrEPA Pesticide Chemical Code 008708

데이터베이스 식별자

CAS
75-62-7
PubChem CID
6383
DTXSID
DTXSID7023930
ChEMBL
CHEMBL160802
UNII
IKJ30QXM63
EC Number
200-886-0
Nikkaji
J48.655H

물성

구조 계산 물성보충 중

XLogP
2.9
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
0
무거운 원자 수
5
형식 전하
0
복잡도
28.4

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Halogenated Aliphatics, Saturated
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
OdorCHLOROFORM-LIKE ODOR
Density · 2건

2.012 @ 25 °C

2.012 @25 °C

Viscosity3.29X10-3 Pa.s @ -21 °C
Color/FormCOLORLESS HEAVY LIQUID
Solubility · 3건

INSOL IN WATER; SOL IN ALL PROP IN ALCOHOL & ETHER

MISCIBLE WITH MANY ORG LIQUIDS

Very soluble in ether and ethanol

Boiling Point · 2건

105 °C

104.2 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits very toxic fumes of /hydrogen chloride/ and /hydrogen bromide/.
Melting Point

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H302 (79.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 190 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 3건

Chemical: Methane, bromotrichloro-

REACH registered substance: Bromotrichloromethane (EC: 200-886-0)

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

Hazards SummaryIntraperitoneal LD50 (rat) = 119 mg/kg; Causes CNS depression; [ChemIDplus] Causes liver injury in animal studies; [HSDB]
Hazard Classes and CategoriesAcute Tox. 4 (79.5%)
Critical Temperature and PressureCritical temperature: 333 °C; critical pressure: 49 atm
Hazardous Reactivities and IncompatibilitiesDURING UNCATALYZED ADDITION OF BROMOTRICHLOROMETHANE TO ETHYLENE VIOLENT EXPLOSION OCCURRED.

안전 및 보호

Disposal Methods · 1건

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.

화학 및 산업

약리 정보

Mechanism of ActionCardiac arrhythmia, possibly aggravated by elevated levels of catecholamines due to stress ... is suggested as the cause of these adverse responses, which may lead to death. /Fluorocarbons/
Metabolism/Metabolites · 3건

AFTER ORAL ADMIN OF BROMOTRICHLOROMETHANE TO RATS, FORMATION OF RADICAL CBRCL2 AND CCL3 BY LIVER METABOLISM MAY OCCUR.

UTILIZING THE SPIN-TRAPPING AGENT PHENYL-TERT-BUTYL NITRONE, A FREE RADICAL, CCL3, WAS DETECTED WHICH IS PRODUCED FROM CARBON TETRACHLORIDE OR BROMOTRICHLOROMETHANE DURING ENZYMIC OXIDATION OF NADPH BY RAT LIVER MICROSOMES.

THE FREE CHLOROFORM RADICAL, BISALLYL RADICAL, & BROMODICHLOROMETHANE RADICAL WERE DETECTED IN RAT LIVERS POISONED WITH BROMOTRICHLOROMETHANE.

용도 및 제조

Uses · 4건

Used in organic synthesis and as a flame retardant; [HSDB]

ORGANIC SYNTHESIS

FLAME RETARDANT

Addition /to isoprene/ is induced using bromotrichloromethane in a 3:1 mol ratio to isoprene by x-irradiation at 60 Gy/min. The main reaction yields a mixture of ca 75% 1,4 and 25% 4,1 addition product

Methods of ManufacturingAt 225-275 °C bromination of the /chloroform/ vapor yields bromochloromethanes: CCl3Br, CCl2Br2, CClBr3
General Manufacturing InformationMethane, bromotrichloro-: ACTIVE

관련 반응

64건
반응 기록 만들기
HRID 63200 반응식
HRID 63200반응물로uspto-grants-2016_09
HRID 70027 반응식
HRID 70027반응물로uspto-grants-2014_09
HRID 100733 반응식
HRID 100733반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 102089 반응식
HRID 102089반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 126658 반응식
HRID 126658반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 229632 반응식
HRID 229632반응물로uspto-grants-2009_07
HRID 229634 반응식
HRID 229634반응물로uspto-grants-2009_07
HRID 245938 반응식
HRID 245938반응물로uspto-grants-2014_02
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화합물 노트

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-5.7 °C
Vapor Pressure · 3건

39.0 [mmHg]

39 mm Hg at 25 °C

39 [mm Hg] @25 °C

물리화학적 성질

녹는점
-5.7 °C · -5.7 °C
끓는 점
105 °C · 105 °C
밀도
2.012 g/cm3 · 2.012 g/cm3(Temp: 25 °C)
Protective Action Criteria (PAC) · 3건

0.71 [mg/m3]

7.9 [mg/m3]

47 [mg/m3]

독성 정보

Interactions · 5건

HEPATOCYTES FROM LIVERS OF RATS FED A SEMISYNTHETIC VITAMIN E-SUPPLEMENTED DIET WERE SLIGHTLY MORE PROTECTED FROM PEROXIDATION AND CELLULAR DAMAGE INDUCED BY BROMOTRICHLOROMETHANE TREATMENT THAN WERE HEPATOCYTES FROM RATS FED A VITAMIN E-DEFICIENT DIET.

WHEN INCUBATED FOR 15 MIN IN AIR WITH RAT LIVER MICROSOMES FROM PHENOBARBITAL-TREATED RATS, A NADPH-GENERATING SYSTEM, AND GSH (5 MILLIMOLAR), BROMOTRICHLOROMETHANE WAS CONVERTED TO DIGLUTATHIONYL DITHIOCARBONATE.

WHEN ISOLATED RAT HEPATOCYTES WERE INCUBATED WITH 2 MILLIMOLAR BROMOTRICHLOROMETHANE, INCR IN THE NUMBER OF CELLS TAKING UP TRYPAN BLUE, RELEASING LACTATE DEHYDROGENASE OR FORMING MALONDIALDEHYDE WAS OFFSET BY ADDING 1X10-4 MOLAR 2-HYDROXYESTRADIOL OR (+)-CYANIDANOL-3.

PROTECTIVE EFFECTS OF CADMIUM ACETATE IN TRICHLOROBROMOMETHANE POISONING.

For more Interactions (Complete) data for BROMOTRICHLOROMETHANE (6 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 567(SRC), determined from an estimated log Kow(2,SRC) and a regression-derived equation(3), indicates that bromotrichloromethane is expected to have low mobility in soil(SRC). Volatilization of bromotrichloromethane from moist soil surfaces is expected (SRC) given an estimated Henry's Law constant of 3.7X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of bromotrichloromethane from dry soil surfaces may exist(SRC) based on a measured vapor pressure of 39 mm Hg(5). Based upon the highly halogenated structure of bromotrichloromethane, biodegradation in soil is expected to be slow(6,SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 567(SRC), determined from an estimated log Kow of 2.5(2,SRC) and a regression-derived equation(3), indicates that bromotrichloromethane is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.7X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.7 hrs and 6.6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 49(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate. Based upon the highly halogenated structure of bromotrichloromethane, biodegradation in water is expected to be slow(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromotrichloromethane, which has a measured vapor pressure of 39 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Based on bromotrichloromethane's structural similarity to bromotrifluoromethane, it is expected to slowly degrade in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for bromotrichloromethane's reaction in air is estimated to be greater than 44 years(3), based on bromotrifluoromethane's rate constant of <5.0X10-16 cu cm/molecule-sec at 25 °C(3). Photolysis may occur based on bromotrichloromethane's structural similarity to other halogenated methane compounds but not at an environmentally important rate(4).

Food Survey ValuesBromotrichloromethane was identified as a volatile compound from bacon(1). Bromotrichloromethane was identified as a meat volatile from pork(2).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Milk ConcentrationsTrace amounts of bromotrichloromethane were identified in pasteurized milk(1).
EPA IRIS InformationBromotrichloromethane
Soil Adsorption/Mobility · 1건

The Koc of bromotrichloromethane is estimated as approximately 567(SRC), using an estimated log Kow of 2.5(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that bromotrichloromethane is expected to have low mobility in soil(SRC).

Natural Pollution SourcesBromotrichloromethane has been identified as a volatile compound in both bacon(1) and pork(2).
Human Toxicity ExcerptsToxic by ingestion and inhalation of fumes.
Artificial Pollution SourcesBromotrichloromethane's production and use in organic syntheses(1) may result in its release to the environment(SRC).
Environmental BiodegradationBiodehalogenation of bromotrichloromethane by hydrogenolysis occurred in cultures with Pseudomonas putida(1). Based upon the highly halogenated structure of bromotrichloromethane, biodegradation is expected to be slow(2).
Environmental Bioconcentration · 1건

An estimated BCF value of 49 was calculated for bromotrichloromethane(SRC), using an estimated log Kow of 2.5(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is moderate(SRC).

안전 데이터

신호 어
Warning
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302