Chemistry:Bromodiiodomethane
Bromodiiodomethane is a trihalomethane with the chemical formula CHBrI
2.[1] This is a halomethane containing one bromine atom and two iodine atoms attached to the methane backbone.
Natural occurrence
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
- ↑ 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. https://pubs.acs.org/doi/10.1021/jo011132t. Retrieved 29 August 2025.
- ↑ Buckingham, John (2 December 1993) (in en). Dictionary of Natural Products. CRC Press. p. 739. ISBN 978-0-412-46620-5. https://books.google.com/books?id=1W0NUD42fA4C&dq=Bromodiiodomethane&pg=PA739. Retrieved 29 August 2025.
- ↑ Buckingham, John (2 December 1993) (in en). Dictionary of Natural Products. CRC Press. p. 232. ISBN 978-0-412-46620-5. https://books.google.com/books?id=1W0NUD42fA4C&dq=Bromodiiodomethane&pg=PA739. 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. https://www.sciencedirect.com/science/article/abs/pii/S004040200200532X. Retrieved 29 August 2025.
- ↑ 5.0 5.1 5.2 "Bromodiiodomethane | CAS 557-95-9 | SCBT - Santa Cruz Biotechnology" (in en). scbt.com. https://www.scbt.com/p/bromodiiodomethane-557-95-9?srsltid=AfmBOoqFCkinEplVQ7MgfHj-Lkc8ToOEKkUN9e9TP25XmmHPyJ9qy1zx.
- ↑ 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. https://shop.thieme.de/en/Houben-Weyl-Methods-of-Organic-Chemistry-Vol.-E-17a-4th-Edition-Supplement/9783131819444. Retrieved 29 August 2025.
- ↑ "CAS 557-95-9 Bromodiiodomethane - Alfa Chemistry". alfa-chemistry.com. https://www.alfa-chemistry.com/product/bromodiiodomethane-cas-557-95-9-319249.html.
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