Bromochloroiodomethane
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| Names | |
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| Preferred IUPAC name
bromo-chloro-iodomethane | |
| Other names
IBCM, chlorobromoiodomethane[1]
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| CHBrClI | |
| Molar mass | 255.28 g·mol−1 |
| Appearance | Light-sensitive liquid |
| Density | 2.9 g/cm³ |
| Boiling point | 157.4 °C (315.3 °F; 430.5 K) |
| poorly soluble | |
| Hazards | |
| GHS labelling:[2] | |
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| Warning | |
| H315, H317, H319 | |
| P280, P305, P338, P351 | |
| Flash point | 69.2±18.4 °C |
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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Bromochloroiodomethane is a trihalomethane with the chemical formula CHBrClI.[3] This complex organic compound is characterized by having three halogen atoms—bromine, chlorine, and iodine—bonded to a methane backbone.[4] The compound has R and S configurations.[5][6]
Synthesis
It can be prepared by reacting a solution of bromodiiodomethane in carbon tetrachloride with a solution of antimony pentachloride in dichloromethane at 0 °C.[7]
Chemical properties
Like other trihalomethanes, it can be deprotonated in situ at low temperatures to give chlorobromoiodomethyl anions. For example, it can react with phenylmercuric chloride in the presence of potassium tert-butoxide to form phenyl(chlorobromoiodomethyl)mercury.[8]
Physical properties
The compound forms a pale yellow liquid that is soluble in organic solvents but poorly soluble in water.[4]
Uses
The compound is primarily used as a reagent in organic synthesis and as a building block for more complex molecules.[4]
References
- ^ "Bromochloroiodomethane | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp. Retrieved 30 August 2025.
- ^ "Bromochloroiodomethane | 1X200MG | CHBrClI | 676461 | 34970-00-8". hpc-standards.com. Retrieved 30 August 2025.
- ^ "Bromochloroiodomethane | CAS 34970-00-8 | SCBT - Santa Cruz Biotechnology". scbt.com. Retrieved 30 August 2025.
- ^ a b c "CAS 34970-00-8: bromo(chloro)iodomethane | CymitQuimica". cymitquimica.com. Retrieved 29 August 2025.
- ^ Manglik, Mr Rohit (24 November 2024). Advanced Organic Chemistry. EduGorilla Publication. p. 94. ISBN 978-93-7093-318-7. Retrieved 30 August 2025.
- ^ Flowers, James L.; Review, Princeton; Silver, Theodore (2004). Cracking the MCAT with CD-ROM. The Princeton Review. p. 751. ISBN 978-0-375-76352-6. Retrieved 30 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 29 August 2025.
- ^ Charette, A.B.; Aggarwal, V.K.; Aitken, R.A.; Cordero, F.; Cicchi, S. (2014). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 22: Three Carbon-Heteroatom Bonds: Thio-, Seleno-, and Tellurocarboxylic Acids and Derivatives; Imidic Acids and Derivatives; Ortho Acid Derivatives (1. Auflage ed.). Stuttgart: Thieme. p. 662. ISBN 978-3-13-171961-4. Retrieved 29 August 2025.