Bromochloroiodomethane

Bromochloroiodomethane

Names
Preferred IUPAC name bromo-chloro-iodomethane
Other names IBCM, chlorobromoiodomethane [1]
Identifiers
CAS Number	34970-00-8  Y
3D model (JSmol)	Interactive image
PubChem CID	37017
CompTox Dashboard (EPA)	DTXSID9021502
InChI InChI=1S/CHBrClI/c2-1(3)4/h1H Key: WUHPSARYLVYQOT-UHFFFAOYSA-N
SMILES C(Cl)(Br)I
Properties
Chemical formula	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)
Solubility in water	poorly soluble
Hazards
GHS labelling: [2]
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319
Precautionary statements	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

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 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

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. "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.