Bromofluoroiodomethane
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| Names | |
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| Preferred IUPAC name
Bromo(fluoro)iodomethane | |
| Other names
bromo-fluoro-iodo-methane
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| Properties | |
| CHBrFI | |
| Molar mass | 238.826 g·mol−1 |
| Appearance | Light yellow liquid |
| Density | 2.9 g/cm3 |
| Boiling point | 102[1] °C (216 °F; 375 K) |
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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Bromofluoroiodomethane is a trihalomethane with the chemical formula CHBrFI.[2] This complex organic compound is characterized by having three halogen atoms—fluorine, bromine, and iodine—attached to a methane backbone.[3] The molecule is chiral.[4][5]
Synthesis
The compound can be prepared by reacting silver bromoacetate with iodine at 180-260 °C in a vacuum, or by reacting diiodomethane with mercury difluoride at 60 °C.[6]
- CHBrI2 + HgF2 ⟶ CHBrFI + HgI2
Ethyl zinc iodide reacts with difluoroiodomethane to produce difluoromethyl zinc iodide, which is tautomerized with fluoroiodomethyl zinc fluoride. It can also react with bromine to produce bromofluoroiodomethane.[7]
References
- ^ Mázor, L. (3 September 2013). Analytical Chemistry of Organic Halogen Compounds: International Series in Analytical Chemistry. Elsevier. p. 220. ISBN 978-1-4831-6065-8. Retrieved 31 August 2025.
- ^ "bromofluoroiodomethane". chemsrc.com. Retrieved 31 August 2025.
- ^ "Bromofluoroiodomethane | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp. Retrieved 31 August 2025.
- ^ Webb, G. A. (2007). Nuclear Magnetic Resonance: Volume 36. Royal Society of Chemistry. p. 114. ISBN 978-0-85404-362-0. Retrieved 31 August 2025.
- ^ Aggarwal, V. K. (2005). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Thieme. p. 656. ISBN 978-3-13-118731-4. Retrieved 31 August 2025.
- ^ Li, Dong Bo; Ng, Siu-Choon; Novak, Igor (15 July 2002). "Novel synthetic approaches to CHBrFI, CHClFI and CHBrClI". Tetrahedron. 58 (29): 5923–5926. doi:10.1016/S0040-4020(02)00532-X. ISSN 0040-4020. Retrieved 31 August 2025.
- ^ Beaulieu, Louis-Philippe B.; Schneider, Jakob F.; Charette, André B. (29 May 2013). "Highly Enantioselective Simmons–Smith Fluorocyclopropanation of Allylic Alcohols via the Halogen Scrambling Strategy of Zinc Carbenoids". Journal of the American Chemical Society. 135 (21): 7819–7822. Bibcode:2013JAChS.135.7819B. doi:10.1021/ja402393w. ISSN 0002-7863. PMID 23659635. Retrieved 31 August 2025.