Bromochloroiodomethane

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Bromochloroiodomethane
Names
Preferred IUPAC name
bromo-chloro-iodomethane
Other names
IBCM, chlorobromoiodomethane[1]
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CHBrClI/c2-1(3)4/h1H
    Key: WUHPSARYLVYQOT-UHFFFAOYSA-N
  • C(Cl)(Br)I
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]
GHS07: Exclamation mark
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).

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

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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

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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

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The compound forms a pale yellow liquid that is soluble in organic solvents but poorly soluble in water.[4]

Uses

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The compound is primarily used as a reagent in organic synthesis and as a building block for more complex molecules.[4]

References

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  1. ^ "Bromochloroiodomethane | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp. Retrieved 30 August 2025.
  2. ^ "Bromochloroiodomethane | 1X200MG | CHBrClI | 676461 | 34970-00-8". hpc-standards.com. Retrieved 30 August 2025.
  3. ^ "Bromochloroiodomethane | CAS 34970-00-8 | SCBT - Santa Cruz Biotechnology". scbt.com. Retrieved 30 August 2025.
  4. ^ a b c "CAS 34970-00-8: bromo(chloro)iodomethane | CymitQuimica". cymitquimica.com. Retrieved 29 August 2025.
  5. ^ Manglik, Mr Rohit (24 November 2024). Advanced Organic Chemistry. EduGorilla Publication. p. 94. ISBN 978-93-7093-318-7. Retrieved 30 August 2025.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.