Carbon tetrabromide Property

Melting point:

88-90 °C(lit.)

Boiling point:

190 °C(lit.)

Density 

3,42 g/cm³

vapor pressure 

40 mm Hg ( 96 °C)

refractive index 

1.5942

Flash point:

190°C

storage temp. 

Store below +30°C.

solubility 

soluble in Chloroform

form 

Crystalline Solid

color 

White to off-white

Water Solubility 

insoluble

BRN 

1732799

Exposure limits

ACGIH: TWA 0.1 ppm; STEL 0.3 ppm
NIOSH: TWA 0.1 ppm(1.4 mg/m3); STEL 0.3 ppm(4 mg/m3)

Dielectric constant

7（22.0℃）

CAS DataBase Reference

558-13-4(CAS DataBase Reference)

NIST Chemistry Reference

Carbon tetrabromide(558-13-4)

EPA Substance Registry System

Carbon tetrabromide (558-13-4)

Safety

Hazard Codes 

Xi,T+,N,Xn

Risk Statements 

37/38-41-36-26-52/53-22

Safety Statements 

26-36-45-27-24-61

RIDADR 

UN 2516 6.1/PG 3

OEB

B

OEL

TWA: 0.1 ppm (1.4 mg/m3), STEL: 0.3 ppm (4 mg/m3)

WGK Germany 

3

RTECS 

FG4725000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29033036

Hazardous Substances Data

558-13-4(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Carbon tetrabromide Chemical Properties,Usage,Production

Description

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.

Chemical Properties

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

Uses

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.

Definition

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

Application

Carbon tetrabromide (CBr4) is a multifunctional chemical reagent widely used in chemical and pharmaceutical industries. It mainly includes:
(1) As a thiophilic reagent, it promotes the one-pot oxidative condensation of amines with N,N'-disubstituted thioureas to give a variety of guanidine derivatives^[1].
(2) As a bromine radical precursor, used in the electrochemical radical bromination and cyclisation sequence of enoic acid to prepare bromomethylated γ-lactone derivatives^[2].
(3) As a precursor of hydrogen atom transfer reagent, used to generate aromatic carbonyl compounds^[3].
(4) As raw materials or intermediates for organic synthesis. Synthesis of N-sulfonylformamidine from CBr4 and formamide under UVA irradiation. Activated imine intermediates (Vilsmeier-Haack reagent derivatives) were obtained via a photoinduced reaction between CBr4 and formamide^[4].

General Description

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Carbon tetrabromide is incompatible with the following: Strong oxidizers, hexacyclohexyldilead, lithium .

Hazard

A poison; narcotic in high concentration. Liver damage, eye, skin, and upper respiratory tract irritant.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways.

Safety Profile

Poison by subcutaneous and intravenous routes. Narcotic in high concentration. Mixture with Li particles is an impact-sensitive explosive. Explodes on contact with hexacyclohexylddead. When heated to decomposition it emits toxic fumes of Br-. See also CHLORINATED HYDROCARBONS, ALIPHATIC.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24-48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray.

Environmental Fate

Carbon tetrabromide inhibits protein synthesis and causes lipid peroxidation, both of which may be involved in cell injury or death mediated by free radicals.

storage

Color Code—Green: General storage may be used.Prior to working with carbon tetrabromide you should betrained on its proper handling and storage. Store in tightlyclosed containers in a cool, well-ventilated area away fromoxidizers and other incompatible materials listed above.

Shipping

UN2516 Carbon tetrabromide, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

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.]

Toxicity evaluation

Carbon tetrabromide is a colorless nonflammable solid at room temperature. It is insoluble in water, but soluble in several organic solvents such as alcohol, ether, and chloroform. Its specific gravity is 3.42, melting point is 90°C, boiling point is 189°C, and vapor pressure is 0.72 torr at 25°C. Production and use of carbon tetrabromide may result in its release in the environment through various hazardous waste streams. Carbon tetrabromide is expected to have very high mobility in soil and volatilizes slowly from dry soil surface. Its biodegradation is expected to be slow and to exist solely as a vapor in the ambient atmosphere. It is not expected to adsorb to suspended solids and sediment in the water column. Its potential for bioconcentration in aquatic organisms is moderate.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, lithium and hexacyclohexyldiilead, since violent reactions may occur.

Waste Disposal

Purify by distillation and return to suppliers.

References

[1] B. YADAV; S. K S; N Srivastava. Carbon Tetrabromide-Mediated Guanylation of Amines with N,N′-Disubstituted Thioureas: An Easy Access to Guanidines[J]. Russian Journal of Organic Chemistry, 2024. DOI:10.1134/S1070428023100093.
[2] KYEONG SEOP KIM;Dae Y K. Electrochemical bromolactonization of alkenoic acids with carbon tetrabromide: Synthesis of bromomethylated γ-lactones[J]. Accounts of Chemical Research, 2022. DOI:10.1080/00397911.2022.2028843.
[3] CHUNBO BO. Visible-Light-Initiated Air-Oxygenation of Alkylarenes to Carbonyls Mediated by Carbon Tetrabromide in Water[J]. ACS Applied Polymer Materials, 2023. DOI:10.1002/cssc.202301015.
[4] QUENTIN CHEVRIER, LéO BETTONI*; Synthesis of N-Sulfonyl Formamidines by Direct Condensation between Sulfonamide and Formamide Enabled by a Photogenerated Vilsmeier-Type Reagent[J]. ACS Applied Electronic Materials, 2024. DOI:10.1021/acs.joc.4c0216010.1021/acs.joc.4c02160.