| Identification | More | [Name]
Carbon tetrabromide | [CAS]
558-13-4 | [Synonyms]
CARBON TETRABROMIDE
PERBROMOMETHANE
TETRABROMOETHANE
TETRABROMOMETHANE
Bromid uhlicity
bromiduhlicity
Carbon bromide
Carbon bromide (CBr4)
carbon(IV)bromide
carbonbromide
carbonbromide(cbr4)
CBr4
Kohlenstofftetrabromid
Methane tetrabromide
Methane, tetrabromo-
methane,tetrabromide
Methane,tetrabromo-
methanetetrabromide
Tetrabrommethan
tetrabromo-methan | [EINECS(EC#)]
209-189-6 | [Molecular Formula]
CBr4 | [MDL Number]
MFCD00000117 | [Molecular Weight]
331.63 | [MOL File]
558-13-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Carbon tetrabromide, is a colorless powder,
white crystalline solid, or yellow-brown crystals. Slight
odor | [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 | [Fp ]
190°C | [storage temp. ]
Store below +30°C. | [solubility ]
soluble in Chloroform | [form ]
Crystalline Solid | [color ]
White to off-white | [Water Solubility ]
insoluble | [Detection Methods]
GC | [BRN ]
1732799 | [Dielectric constant]
7（22.0℃） | [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) | [Uses]
Organic synthesis. | [CAS DataBase Reference]
558-13-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Carbon tetrabromide(558-13-4) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
558-13-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,T+,N | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R36:Irritating to the eyes.
R26:Very Toxic by inhalation.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S27:Take off immediately all contaminated clothing .
S24:Avoid contact with skin .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [OEB]
B | [OEL]
TWA: 0.1 ppm (1.4 mg/m3), STEL: 0.3 ppm (4 mg/m3) | [RIDADR ]
UN 2516 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
FG4725000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29033036 | [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. | [Hazardous Substances Data]
558-13-4(Hazardous Substances Data) |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
CARBON TETRABROMIDE(558-13-4) is incompatible with the following: Strong oxidizers, hexacyclohexyldilead, lithium . | [Air & Water Reactions]
Insoluble in water. | [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. | [Potential Exposure]
CBr4 is used in organic synthesis. | [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. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy. | [Shipping]
UN2516 Carbon tetrabromide, Hazard Class:
6.1; Labels: 6.1-Poisonous materials. | [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.
| [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 | [Chemical Properties]
Crystalline colorless | [Waste Disposal]
Purify by distillation and
return to suppliers. | [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]. | [Definition]
ChEBI: A one-carbon compound substituted by 4 bromo groups. | [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. | [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. | [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.
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