Tribromoiodomethane

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Tribromoiodomethane
Names
Preferred IUPAC name
Tribromo(iodo)methane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CBr3I/c2-1(3,4)5
    Key: JWCWGHDHZXYEGQ-UHFFFAOYSA-N
  • C(Br)(Br)(Br)I
Properties
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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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

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

References

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  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.