Bromodiiodomethane

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Bromodiiodomethane
Bromodiiodomethane.png
Names
Preferred IUPAC name
Bromo(diiodo)methane
Other names
Diiodobromomethane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/CHBrI2/c2-1(3)4/h1H
    Key: PTGIGXMFLYACDM-UHFFFAOYSA-N
  • C(Br)(I)I
Properties
CHBrI2
Molar mass 346.732 g·mol−1
Appearancelight yellow solid
Density 3.6±0.1 g/cm³
Melting point 49 °C (120 °F; 322 K)
Boiling point 221.5 °C (430.7 °F; 494.6 K)
soluble
Hazards
Flash point 87.8±18.4 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bromodiiodomethane is a trihalomethane with the chemical formula CHBrI2. [1] This is a halomethane containing one bromine atom and two iodine atoms attached to the methane backbone.

Contents

Natural occurence

The compound is found in the oil of the alga Asparagopsis taxiformis . [2] [3]

Synthesis

It can be obtained by reacting triiodomethane with bromine in carbon tetrachloride at 0 °C with a yield of 52%. [4]

Chemical properties

The pronounced reactivity of bromodiiodomethane is attributed to its molecular structure, which contains two iodine and two bromine atoms. [5]

It can react with antimony pentachloride to produce bromochloroiodomethane. It can form bromoiodocarbene in the presence of benzyltriethylammonium chloride in a concentrated solution of sodium hydroxide, and react with alkenes to form a three-membered ring. [6]

Physical properties

Bromodiiodomethane forms a light yellow solid [7] that is highly soluble in water, ethanol, and various organic solvents. It exhibits significant reactivity, making it valuable in the synthesis of a wide array of compounds, including dyes and other organic materials. [5]

Uses

Its role as a reagent spans multiple scientific disciplines such as organic synthesis, chromatography, and spectroscopy. In organic synthesis, it is a crucial component, while in chromatography, it aids in separating complex mixtures. Additionally, in spectroscopy, it facilitates the structural analysis of organic molecules. [5]

References

  1. ↑ Novak, Igor; Li, Dong Bo; Potts, Anthony W.; Shareef, Abdulla; Kovač, Branka (1 May 2002). "Halogen−Halogen Interactions in Halomethanes". The Journal of Organic Chemistry . 67 (10): 3510–3513. doi:10.1021/jo011132t. ISSN   0022-3263. PMID   12003569 . Retrieved 29 August 2025.
  2. ↑ Buckingham, John (2 December 1993). Dictionary of Natural Products. CRC Press. p. 739. ISBN   978-0-412-46620-5 . Retrieved 29 August 2025.
  3. ↑ Buckingham, John (2 December 1993). Dictionary of Natural Products. CRC Press. p. 232. ISBN   978-0-412-46620-5 . Retrieved 29 August 2025.
  4. ↑ 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.
  5. 1 2 3 "Bromodiiodomethane | CAS 557-95-9 | SCBT - Santa Cruz Biotechnology". scbt.com . Retrieved 29 August 2025.
  6. ↑ de Meijere, A.; Baird, M.S.; Bertrand, G.; de Kimpe, N.; Fedorynski, M. (2014). Houben-Weyl Methods of Organic Chemistry Vol. E 17a, 4th Edition Supplement: Carbocyclic Three-Membered Ring Compounds, Cyclopropanes: Synthesis (4 ed.). Stuttgart: Thieme. p. 697. ISBN   978-3-13-181944-4 . Retrieved 29 August 2025.
  7. ↑ "CAS 557-95-9 Bromodiiodomethane - Alfa Chemistry". alfa-chemistry.com. Retrieved 29 August 2025.
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