四臭化炭素

Carbon tetrabromide

HCID 11205CAS 558-13-4

基本情報

標準SMILES
BrC(Br)(Br)Br
InChIKey
HJUGFYREWKUQJT-UHFFFAOYSA-N
分子式
CBr4
平均分子量
331.63 g/mol
単同位体質量
327.6733484

概要

Carbon tetrabromide appears as a colorless crystalline solid. Much more dense than water and insoluble in water. Toxic by ingestion. Vapors are narcotic in high concentration. Used to make other chemicals.

名称と識別子

優先名称
Carbon tetrabromide
IUPAC
tetrabromomethane
現地名
四臭化炭素
英語名
Carbon tetrabromide
分子式
CBr4
分子量
331.63

名称と別名

Carbon tetrabromideTETRABROMOMETHANE558-13-4Methane, tetrabromo-Carbon bromideCBr4Methane tetrabromideCarbon bromide (CBr4)Bromid uhlicityTetrabrommethanMethane, tetrabromidetetrabromidocarbon
名称をさらに表示
四臭化炭素テトラブロモメタンテトラブロムメタン四臭化炭素, vacuum sublimed (99.998%-C) PURATREMPERBROMOMETHANETETRABROMOETHANETetrabroMoMethCarbon tetrabroMide, 98% 100GRcarbonbromidebromiduhlicity
TetrabromkohlenstoffKohlenstofftetrabromidNLH657095LNSC-6179DTXSID8060327CHEBI:47875Carboneum BromatumRefChem:58674

データベース識別子

CAS
558-13-4
PubChem CID
11205
DTXSID
DTXSID8060327
ChEBI
CHEBI:47875
UNII
NLH657095L
EC Number
209-189-6
Nikkaji
J2.667K

物性

構造計算による物性

XLogP
3.4
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
0
重原子数
5

実験および物理化学的性質

SolventsSolvents -> Brominated Solvents
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 件

log Kow= 3.42

3.42

Odor · 2 件

Slight odor.

Lacrymator

Density · 5 件

3.42 (NIOSH, 2024) - Denser than water; will sink

2.9608 @ 100 °C/4 °C

Relative density (water = 1): 3.42

3.42

3.42

Color/Form · 3 件

Colorless, monoclinic tablets

Colorless crystals

Colorless to yellow-brown crystals.

物理化学的性質

融点
88 · 88-90 °C(lit.)
沸点
190 °C · 190 °C(lit.)
比重(密度)
3 · 3,42 g/cm3
蒸気圧
40 mm · 40 mm Hg ( 96 °C)
屈折率
1.5942 · 1.5942
闪点
190 °C · 190°C

化学的性質

化学的特性Carbon tetrabromide, is a colorless powder, white crystalline solid, or yellow-brown crystals. Slight odor

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 111 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

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

危険有害性情報

Regulatory Information · 3 件

Chemical: Methane, tetrabromo-

Carbon tetrabromide: 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.)

DOT LabelPoison
Fire Hazards · 3 件

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialNot flammable by standard tests in air
Health Hazards · 2 件

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

Hazards Summary · 1 件

In an acute study of mice, carbon tetrabromide was determined to be 2.2 times more toxic to the liver than carbon tetrachloride. It causes significant eye irritation (tearing) in workers even at lower exposure levels. [ACGIH] A lachrymator; [HSDB] Inhalation of high concentrations can cause CNS depression; Causes corrosive burns to eyes [ICSC]

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. 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. Refer for medical attention .

Accidental Release Measures · 2 件

· 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.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

First Aid · 3 件

Excerpt from NIOSH Pocket Guide for Carbon tetrabromide:

General First Aid:

(General first aid procedures)

Safe StorageWell closed.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

Treatment · 1 件

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Target OrgansEyes, skin, respiratory system, liver, kidneys
Health Effects · 1 件

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that tetrabromomethane is expected to have very high mobility in soil(SRC). Volatilization of tetrabromomethane from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-4 atm-cu m/mole(SRC), from its vapor pressure, 0.72 mm Hg(3) and water solubility, 240 mg/l(4). Tetrabromomethane is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.72 mm Hg(4). Based upon the highly halogenated structure of tetrabromomethane, biodegradation is expected to be slow(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that tetrabromomethane is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces may occur based on an estimated Henry's Law constant of 4.9X10-4 atm-cu m/mole(SRC), from its vapor pressure, 0.72 mm Hg(4) and water solubility, 240 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 4.0 hrs and 8.2 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 86(SRC), from its log Kow value of 3.42(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate. Based upon the highly halogenated structure of tetrabromomethane, biodegradation is expected to be slow(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetrabromomethane, which has a vapor pressure of 0.72 mm Hg at 30 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. The rate constant for the vapor-phase reaction of tetrabromomethane with photochemically-produced hydroxyl radicals could not be estimated but is expected to be very slow since there are no abstractable hydrogens(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 3 件

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

inhalation, ingestion, skin and/or eye contact

Oral (L626) ; inhalation (L626) ; dermal (L626)

法規制情報

Atmospheric Standards · 1 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. Carbon tetrabromide is produced, as an intermediate or a final product, by process units covered under this subpart.

安全データ

OEB
B
OEL
TWA: 0.1 ppm (1.4 mg/m3), STEL: 0.3 ppm (4 mg/m3)
wgk
3
tsca
TSCA listed
rtecs
FG4725000
ridadr
UN 2516

化学と産業

薬理情報

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/
Biological Half-LifeFor bromide (depends on compound and route of administration) whole body: 1 hour to 12 days; [TDR, p. 214]
Metabolism/Metabolites · 3 件

UNDER ANAEROBIC REDUCING CONDITIONS POLYHALOGENATED METHANES, CBR4, FORM COMPLEXES WITH FERROUS CYTOCHROME P450. CARBON MONOXIDE DETECTED AS A METABOLIC PRODUCT OF THE INTERACTION.

Carbon tetrabromide is metabolized in vitro to produce carbon monoxide but the in vivo significance has not been established.

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

用途と製造

Uses · 4 件

Used in organic syntheses; [ACGIH]

Organic synthesis

CHEMICAL INTERMEDIATE

It is used as a solvent for greases, waxes and oils, in plastic and rubber industry for blowing, vulcanization, and polymerization, as a sedative and as an intermediate in manufacturing agrochemicals. Due to its non-flammability it is used as an ingredient in fire resistant chemicals. It is also used for separating minerals because of its high density. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

General Manufacturing InformationMethane, tetrabromo-: ACTIVE
応用分野 · 6 件

解説CBr4(331.63).CHBr3またはCS2に臭化ヨウ素を作用させて得られる.四臭化炭素は,淡黄色の固体で2形がある.α形は単斜晶系.融点90 ℃,沸点189 ℃(やや分解する).密度2.96 g cm-3(99.5 ℃).β形は立方晶系結晶.融点94.3 ℃.転移点46.7 ℃.正四面体構造で,原子間距離C-Br0.1942 nm.エタノール,エーテル,クロロホルムに可溶,水に不溶.有機合成の臭素化剤,半導体基板のエッチング剤,写真材料の製造などに用いられる.森北出版「化学辞典(第2版)

用途有機合成中間体 感光性物質用

用途有機合成原料、電子工業材料。

説明Carbon tetrabromide is considered a highly toxic chemical, may be fatal if inhaled, swallowed, or absorbed through skin. It is metabolized in vitro to produce carbon monoxide but the in vivo significance has not been established. Under anaerobic reducing conditions it forms complexes with ferrous cytochrome P450. Carbon monoxide is detected as a metabolic product of the interaction. Carbon tetrabromide’s production and use in organic syntheses may result in its release to the environment through various waste streams. Carbon tetrabromide has been isolated from red algae, Asparagopsis toxiformis, found in the ocean near Hawaii. It was detected in water from treated chlorinated seawater used for drinking at oil platforms. Occupational exposure to carbon tetrabromide may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. The general population may be exposed to carbon tetrabromide via ingestion of drinking water. Acute exposures to high concentrations may cause upper respiratory tract irritation and injury to lungs, liver (hepatotoxicity) and kidneys (nephrotoxicity). Chronic exposure effects at very low levels will be almost entirely limited to liver injury. It is a potent lachrymator even at low exposure concentrations. Although carbon tetrabromide may release bromine ions during metabolism, clinical bromism is not expected to occur.

使用Carbon tetrabromide is used to a limited extent as a chemical intermediate. It has been isolated from red algae, Asparagopsis toxiformis, found in the ocean near Hawaii.

一般的な説明A colorless crystalline solid. Much more dense than water and insoluble in water. Toxic by ingestion. Vapors are narcotic in high concentration. Used to make other chemicals.

調製方法 · 2 件

合成方法ブロモホルムまたは二硫化炭素と臭化ヨウ素の反応から合成される

純化方法Reactive bromide is removed from CBr4 by refluxing with dilute aqueous Na2CO3, then steam distilling, crystallising from EtOH, and drying in the dark under vacuum. [Sharpe & Walker J Chem Soc 157 1962.] It can be sublimed at 70o and low pressure. [Beilstein 1 IV 85.]

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補足説明

定義ChEBI: A one-carbon compound substituted by 4 bromo groups.

関連反応

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