Tribromoiodomethane

Tribromoiodomethane

Names
Preferred IUPAC name Tribromo(iodo)methane
Identifiers
CAS Number	14349-80-5  Y
3D model (JSmol)	Interactive image
ChemSpider	11570030
PubChem CID	12542274
InChI InChI=1S/CBr3I/c2-1(3,4)5 Key: JWCWGHDHZXYEGQ-UHFFFAOYSA-N
SMILES C(Br)(Br)(Br)I
Properties
Chemical formula	CBr3I
Molar mass	378.627 g·mol−1
Appearance	golden-yellow crystalline [1]
Density	3.7 g/cm³
Boiling point	226.8 °C (440.2 °F; 499.9 K)
Hazards
Flash point	91 °C
Related compounds
Related compounds	Tribromochloromethane, Tetrabromomethane, Dibromodiiodomethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tribromoiodomethane is a tetrahalomethane with the chemical formula CBr₃I. ^{[2] [3]} This is a halomethane containing three bromine atoms and one iodine atom attached to the methane backbone. ^[4]

Synthesis

The compound can be obtained by reacting carbon tetrabromide and sodium iodide in acetone with a yield of 30%. The remaining products of the reaction are brominated acetone and trace amounts of bromotriiodomethane. ^[5]

CBr₄ + NaI + acetone → CBr₃I + CBrI₃ + brominated acetone ^[6]

Tribromoiodomethane can also be produced by the reaction of nitrotribromomethane with a small amount of potassium iodide: ^[7]

CBr₃NO₂ + KI → CBr₃I + KNO₂

Uses

The compound can be used to introduce tribromomethyl groups into organic compounds.

References

1. Journal of the Chemical Society Volume 96, Part 1. Journal of the Chemical Society. 1909. p. 867. Retrieved 4 September 2025.
2. Luo, Yu-Ran (9 March 2007). Comprehensive Handbook of Chemical Bond Energies. CRC Press. p. 245. ISBN   978-1-4200-0728-2 . Retrieved 4 September 2025.
3. Comprehensive Organic Functional Group Transformations II: A Comprehensive Review of the Synthetic Literature 1995 - 2003. Elsevier. 16 December 2004. p. 3049. ISBN   978-0-08-052347-7 . Retrieved 4 September 2025.
4. Kotake, Munio (1963). Constants of Organic Compounds. Asakura Publishing Company. p. 15. Retrieved 4 September 2025.
5. Kennedy, John Rider; Vickrey, Thomas M.; Somayajulu, G. R.; Zwolinski, Bruno J. (1 July 1979). "Synthesis of dichloroiodomethane, trichloroiodomethane, dibromoiodomethane, and tribromoiodomethane". Journal of Chemical & Engineering Data . 24 (3): 251–252. doi:10.1021/je60082a003. ISSN   0021-9568 . Retrieved 4 September 2025.
6. Comprehensive Organic Functional Group Transformations, Volume 6 (1. ed.). Oxford: Pergamon Press. 1995. p. 223. ISBN   9780080427041 . Retrieved 4 September 2025.
7. Jacobson, Carl Alfred; Hampel, Clifford A. (1959). Encyclopedia of Chemical Reactions. Reinhold Publishing Corporation. p. 437. Retrieved 4 September 2025.