Bromochloroiodomethane
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| Names | |
|---|---|
| Preferred IUPAC name
bromo-chloro-iodomethane | |
| Other names
IBCM, chlorobromoiodomethane[1] | |
| 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).
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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
[edit]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
[edit]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
[edit]The compound forms a pale yellow liquid that is soluble in organic solvents but poorly soluble in water.[4]
Uses
[edit]The compound is primarily used as a reagent in organic synthesis and as a building block for more complex molecules.[4]
References
[edit]- ↑ "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.
- 1 2 3 "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.
