Bromodiiodomethane
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| Names | |
|---|---|
| Preferred IUPAC name
Bromo(diiodo)methane | |
| Other names
Diiodobromomethane
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| CHBrI2 | |
| Molar mass | 346.732 g·mol−1 |
| Appearance | light 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).
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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.
Natural occurrence
[edit]The compound is found in the oil of the alga Asparagopsis taxiformis.[2][3]
Synthesis
[edit]It can be obtained by reacting triiodomethane with bromine in carbon tetrachloride at 0 °C with a yield of 52%.[4]
Chemical properties
[edit]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
[edit]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
[edit]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
[edit]- ^ 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.
- ^ Buckingham, John (2 December 1993). Dictionary of Natural Products. CRC Press. p. 739. ISBN 978-0-412-46620-5. Retrieved 29 August 2025.
- ^ Buckingham, John (2 December 1993). Dictionary of Natural Products. CRC Press. p. 232. ISBN 978-0-412-46620-5. Retrieved 29 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.
- ^ a b c "Bromodiiodomethane | CAS 557-95-9 | SCBT - Santa Cruz Biotechnology". scbt.com. Retrieved 29 August 2025.
- ^ 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.
- ^ "CAS 557-95-9 Bromodiiodomethane - Alfa Chemistry". alfa-chemistry.com. Retrieved 29 August 2025.