Bromotrichloromethane

Bromotrichloromethane

Names
Preferred IUPAC name Bromo(trichloro)methane
Other names Carbon bromotrichloride
Identifiers
CAS Number	75-62-7  Y
3D model (JSmol)	Interactive image
ChemSpider	6143
ECHA InfoCard	100.000.806
EC Number	200-886-0
PubChem CID	6383
UNII	IKJ30QXM63
CompTox Dashboard (EPA)	DTXSID7023930
InChI InChI=1S/CBrCl3/c2-1(3,4)5 Key: XNNQFQFUQLJSQT-UHFFFAOYSA-N
SMILES C(Cl)(Cl)(Cl)Br
Properties
Chemical formula	CBrCl3
Molar mass	198.27 g·mol−1
Appearance	colorless liquid
Density	2.401 g/cm³
Melting point	21 °C (70 °F; 294 K)
Boiling point	105 °C (221 °F; 378 K)
Solubility in water	practically insoluble
Hazards
GHS labelling: [1]
Pictograms
Signal word	Warning
Flash point	32.6 °C
Related compounds
Related compounds	Bromodichloromethane Tribromochloromethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bromotrichloromethane is a tetrahalomethane with the chemical formula CBrCl₃. This is a halomethane containing one bromine atom and three chlorine atoms. ^{[2] [3]} Bromotrichloromethane is a volatile, non-flammable, colorless liquid with a pungent odor that is practically insoluble in water but miscible with organic solvents. ^[4]

Synthesis

Bromotrichloromethane can be obtained by treating carbon tetrachloride with hydrogen bromide or aluminum bromide. ^[5] It can also be obtained by reacting trichloromethane with bromine at 225 to 400 °C or potassium trichloroacetate with bromine at 120 °C. ^[6]

Cl₃CCO₂K + Br₂ → CBrCl₃ + CO₂ + KBr

Uses

Bromotrichloromethane is used as a chain transfer agent for the radical polymerization of methacrylates and as a brominating agent. ^[7]

It is used for the addition of Br-CCl₃ across double bonds. ^[2]

References

1. "Bromotrichloromethane". Sigma Aldrich . Retrieved 5 September 2025.
2. Shinokubo, Hiroshi; Oshima, Koichiro; Gu, Zhenhua; Zakarian, Armen; Castiglione, Davide; Pace, Vittorio (2025). "Bromotrichloromethane (CBRCL ₃ )". Encyclopedia of Reagents for Organic Synthesis. pp. 1–10. doi:10.1002/047084289X.rn00250.pub3. ISBN   978-0-471-93623-7.
3. Crich, David (30 May 2013). Reagents for Radical and Radical Ion Chemistry. John Wiley & Sons. p. 12. ISBN   978-1-118-63489-9 . Retrieved 5 September 2025.
4. Anderson, Bruce; Peyster, Ann de; Gad, Shayne C.; Hakkinen, P. J. Bert; Kamrin, Michael; Locey, Betty; Mehendale, Harihara M.; Pope, Carey; Shugart, Lee (31 May 2005). Encyclopedia of Toxicology. Elsevier. ISBN   978-0-08-054800-5 . Retrieved 5 September 2025.
5. Skell, P. S; Baxter, H. N; Tanko, J. M (1 January 1986). "Reactions of BrCl with alkyl radicals" . Tetrahedron Letters . 27 (43): 5181–5184. doi:10.1016/S0040-4039(00)85163-1. ISSN   0040-4039 . Retrieved 5 September 2025.
6. Gilchrist, Thomas L. (1995). Comprehensive Organic Functional Group Transformations (1 ed.). Oxford: Elsevier. p. 221. ISBN   0-08-042704-9 . Retrieved 5 September 2025.
7. "Bromtrichlormethan". gestis.dguv.de. Retrieved 5 September 2025.