tetrabromomethane

• ChemBase ID: 90364
• Molecular Formular: CBr4
• Molecular Mass: 331.6267
• Monoisotopic Mass: 327.673348
• SMILES: BrC(Br)(Br)Br
• Canonical SMILES: BrC(Br)(Br)Br
• InChI: InChI=1S/CBr4/c2-1(3,4)5
• InChIKey: HJUGFYREWKUQJT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrabromomethane
• IUPAC Traditional name: carbon tetrabromide
• Synonyms: Tetrabromomethane; Carbon tetrabromide; Tetrabromomethane; Carbon bromide; Methane tetrabromide; Tetrabromomethane; Carbon tetrabromide; 四溴化碳; 四溴化碳; 四溴甲烷

Database IDs

• CAS Number: 558-13-4
• EC Number: 209-189-6
• MDL Number: MFCD00000117
• Beilstein Number: 1732799
• PubChem SID: 24888767; 24892347; 162077179
• PubChem CID: 11205
• CHEBI ID: 47875
• Chemspider ID: 10732
• Gmelin ID: 26450
• MeSH Name: carbon+tetrabromide
• Wikipedia Title: Tetrabromomethane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.5968134
• LogD (pH = 7.4): 3.5968134
• Log P: 3.5968134
• Molar Refractivity: 2.3038 cm^3
• Polarizability: 15.332903 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless crystals
• Melting Point: 88-90 °C(lit.); 88-90°C; 90-95°C; 92-93 °C; 94.45°C (367.6K)
• Boiling Point: 189.65°C (462.8K); 190 °C(lit.); 190°C; 190°C
• Density: 2.9; 3.42 g mL^-1; 3.420
• Vapor Pressure: 40 mmHg ( 96 °C); 5.33 kPa (at 96.3 °C)
• Heat Capacity: 145.9 J K^-1 mol^-1
• Std enthalpy of combustion: -426.2–-419.6 kJ mol^-1
• Std enthalpy of formation: 26.0–32.8 kJ mol^-1

Safety Information

• Storage Warning: Toxic/Harmful/Irritant/Corrosive/Light Sensitive
• RTECS: FG4725000
• European Hazard Symbols: Nature polluting (N); X; Irritant (Xi); Harmful (Xn)
• UN Number: 2516; UN2516
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22-37/38-41; R37/38, R41, R52/53
• Safety Statements: 26-36; 26-36/37/39-60; S26, S36
• TSCA Listed: 是
• GHS Pictograms: GHS corrosion; GHS exclamation mark; GHS05; GHS07
• GHS Signal Word: DANGER; Danger
• NFPA704:
  

  0

  2

  0
• LD50: 1.8 g kg^-1 (oral, rat); 56 mg kg^-1 (intravenous, mouse)
• GHS Hazard statements: 302, 315, 318, 335; H302-H315-H318-H335; H318-H315-H302-H335
• GHS Precautionary statements: 261, 280, 305+351+338; P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 2516 6.1/PG 3

Product Information

• Purity: ≥97.0% (GC); 98% (dry wt.), may cont. up to ca 6% water; 99%
• Grade: purum; ReagentPlus®
• Empirical Formula (Hill Notation): CBr4

DETAILS

Sigma Aldrich - C11081

Packaging
5, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Brominating agent for Li ester enolates, where bromine tends to give erratic results: J. Org. Chem., 43, 3687 (1978). Exchange reaction with n-BuLi or PhLi in ether at -111^o generates tribromomethyllithium, giving 91% yield on carbonation: Chem. Ber., 101, 3230 (1968).
• In combination with triphenylphosphine, effects the dibromomethylenation of aldehydes to 1,1-dibromoalkenes: J. Am. Chem. Soc., 84, 1745 (1962). Dehydrobromination of the products with n-BuLi provides a valuable aldehyde to alkyne homologation: Tetrahedron Lett., 3769 (1972); 31, 3141 (1990). An improved procedure, suitable for sensitive aldehydes, has been described using triethylamine in the dibromomethylenation step to suppress side reactions, and the hindered base sodium bis(trimethylsilylamide) (NaHMDS) for the elimination step: Tetrahedron Lett., 35, 3529 (1994); Synth. Commun., 25, 3641 (1995):
  
• Also frequently used in combination with triphenylphosphine for the conversion of alcohols to alkyl bromides under mild conditions, applicable to sensitive substrates such as allylic or carbohydrate molecules: Chem. Ind. (London), 1017 (1969); J. Org. Chem., 36, 403 (1971); Synth. Commun., 24, 1117 (1994).