Bromochlorofluoroiodomethane
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| Names | |||
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| Preferred IUPAC name
Bromo(chloro)fluoro(iodo)methane | |||
| Other names
Bromochlorofluoroiodomethane
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| Identifiers | |||
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| CBrClFI | |||
| Molar mass | 273.27 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Bromochlorofluoroiodomethane is a hypothetical haloalkane with all four stable halogen substituents present in it.[1]
Overview
This compound can be seen as a methane molecule, whose four hydrogen atoms are each replaced with a different halogen atom. As the mirror images of this molecule are not superimposable, the molecule has two enantiomers. As one of the simplest such molecules, it is often cited as the prototypical chiral compound.[2] However, since there is no synthetic route known to produce bromochlorofluoroiodomethane, the related simple chiral compound bromochlorofluoromethane is used instead when such a compound is required for research.
Of the chiral halomethanes it has been calculated to have the second lowest thermodynamic stability with only CHClBrI being lower.[3]
References
- ^ "bromochlorofluoroiodomethane | chemical compound | Britannica". www.britannica.com. Retrieved 2021-12-27.
- ^ Comprehensive Organic Functional Group Transformations: Carbon with Three or Four Attached Heteroatoms, Volume 6, Thomas L. Gilchrist (Editor), ISBN 978-0-08-042704-1
- ^ Novak, Igor (1 April 1990). "Electronic Structure of Chiral Halomethanes". Bulletin of the Chemical Society of Japan. 63 (4): 1278–1280. doi:10.1246/bcsj.63.1278. ISSN 0009-2673. Retrieved 28 September 2025.