Bromofluoroiodomethane

Bromofluoroiodomethane

Names
Preferred IUPAC name Bromo(fluoro)iodomethane
Other names bromo-fluoro-iodo-methane
Identifiers
CAS Number	1512-27-2  Y
3D model (JSmol)	Interactive image
ChemSpider	9656646
PubChem CID	11481826
InChI InChI=1S/CHBrFI/c2-1(3)4/h1H Key: FMFUPOAGBUBEFH-UHFFFAOYSA-N
SMILES FC(Br)I
Properties
Chemical formula	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

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

1. 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.
2. "bromofluoroiodomethane". chemsrc.com. Retrieved 31 August 2025.
3. "Bromofluoroiodomethane | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp. Retrieved 31 August 2025.
4. 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.
5. 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.
6. 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.
7. 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.