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Carbon tetrabromide

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Carbon tetrabromide Basic information
Product Name:Carbon tetrabromide
Synonyms:Carbon tetrabroMide, 98% 500GR;Carbon tetrabroMide, 98% 5GR;Fourcarbon broMide;TetrabroMoMethane ReagentPlus(R), 99%;Four broMide carbon;TetrabroMoMeth;Carbon tetrabromide for synthesis;Bromid uhlicity
CAS:558-13-4
MF:CBr4
MW:331.63
EINECS:209-189-6
Product Categories:element halide;Aromatic Hydrocarbons (substituted) & Derivatives;Organics;pharmaceutical
Mol File:558-13-4.mol
Carbon tetrabromide Structure
Carbon tetrabromide Chemical Properties
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
BRN 1732799
Dielectric constant7(22.0℃)
Exposure limitsACGIH: TWA 0.1 ppm; STEL 0.3 ppm
NIOSH: TWA 0.1 ppm(1.4 mg/m3); STEL 0.3 ppm(4 mg/m3)
CAS DataBase Reference558-13-4(CAS DataBase Reference)
NIST Chemistry ReferenceCarbon tetrabromide(558-13-4)
EPA Substance Registry SystemCarbon tetrabromide (558-13-4)
Safety Information
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
OEBB
OELTWA: 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 Data558-13-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Carbon tetrabromide English
SigmaAldrich English
ACROS English
ALFA English
Carbon tetrabromide Usage And Synthesis
DescriptionCarbon 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 PropertiesCarbon tetrabromide, is a colorless powder, white crystalline solid, or yellow-brown crystals. Slight odor
UsesCarbon 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.
DefinitionChEBI: A one-carbon compound substituted by 4 bromo groups.
ApplicationCarbon 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 DescriptionA 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 ReactionsInsoluble in water.
Reactivity ProfileCarbon tetrabromide is incompatible with the following: Strong oxidizers, hexacyclohexyldilead, lithium .
HazardA poison; narcotic in high concentration. Liver damage, eye, skin, and upper respiratory tract irritant.
Health HazardHighly 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 HazardNon-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 ProfilePoison 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 aidIf 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 FateCarbon tetrabromide inhibits protein synthesis and causes lipid peroxidation, both of which may be involved in cell injury or death mediated by free radicals.
storageColor 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.
ShippingUN2516 Carbon tetrabromide, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification MethodsReactive 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 evaluationCarbon 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.
IncompatibilitiesIncompatible 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 DisposalPurify 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.
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