Bromotrichloromethane

Bromotrichloromethane
Names
	Preferred IUPAC name Bromo(trichloro)methane
	Other names Carbon bromotrichloride
Identifiers
CAS Number	75-62-7 ;
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:
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

Physical properties

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

^ "Bromotrichloromethane". Sigma Aldrich. Retrieved 5 September 2025.
^ ^a ^b 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.
^ 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.
^ 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.
^ 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.
^ Gilchrist, Thomas L. (1995). Comprehensive Organic Functional Group Transformations (1 ed.). Oxford: Elsevier. p. 221. ISBN 0-08-042704-9. Retrieved 5 September 2025.
^ "Bromtrichlormethan". gestis.dguv.de. Retrieved 5 September 2025.

[1] "Bromotrichloromethane". Sigma Aldrich. Retrieved 5 September 2025.

[eros-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.

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