Bromochlorofluoromethane or fluorochlorobromomethane, is a chemical compound and trihalomethane derivative with the chemical formula CHBrClF. As one of the simplest possible stable chiral compounds, it is useful for fundamental research into this area of chemistry.[1] However, its relative instability to hydrolysis,[2] and lack of suitable functional groups, made separation of the enantiomers of bromochlorofluoromethane especially challenging,[3] and this was not accomplished until almost a century after it was first synthesised, in March 2005, though it has now been done by a variety of methods.[4][5][6][7] More recent research using bromochlorofluoromethane has focused on its potential use for experimental measurement of parity violation, a major unsolved problem in quantum physics.[8][9][10]
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| Names | |
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| Preferred IUPAC name
Bromo(chloro)fluoromethane | |
| Other names
Bromochlorofluoromethane
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| CHBrClF | |
| Molar mass | 147.37 g·mol−1 |
| Density | 1.953 g/cm3 |
| Melting point | −115 °C; −175 °F; 158 K |
| Boiling point | 36 °C; 97 °F; 309 K |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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See also
edit- Bromochlorodifluoromethane, used in fire extinguishers
- Bromochlorofluoroiodomethane, a theoretical derivative with iodine replacing the hydrogen
References
edit- ^ Berry, Kenneth L.; Sturtevant, Julian M. (1942). "Fluorochlorobromomethane". Journal of the American Chemical Society. 64 (7): 1599–1600. doi:10.1021/ja01259a031.
- ^ Thomas L. Gilchrist. Comprehensive Organic Functional Group Transformations. Volume 6. Synthesis: Carbon with Three or Four Attached Heteroatoms. p228. Pergamon / Elsevier, 1995. ISBN 0-08-042704-9
- ^ Hargreaves, Michael K.; Modarai, Borzoo (1969). "An optically active haloform: (+)-bromochlorofluoromethane". Journal of the Chemical Society D: Chemical Communications. 1: 16. doi:10.1039/C29690000016.
- ^ Canceill, Josette; Lacombe, Liliane; Collet, Andre (1985). "Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailor-made cryptophane and determination of its maximum rotation". Journal of the American Chemical Society. 107 (24): 6993–6996. doi:10.1021/ja00310a041.
- ^ Doyle, Thomas R.; Vogl, Otto (1989). "Bromochlorofluoromethane and deuteriobromochlorofluoromethane of high optical purity". Journal of the American Chemical Society. 111 (22): 8510–8511. doi:10.1021/ja00204a029.
- ^ Grosenick, Heiko; Schurig, Volker; Costante, Jeanne; Collet, André (1995). "Gas chromatographic enantiomer separation of bromochlorofluoromethane". Tetrahedron: Asymmetry. 6 (1): 87–88. doi:10.1016/0957-4166(94)00358-I.
- ^ Pitzer, M.; Kunitski, M.; Johnson, A. S.; Jahnke, T.; Sann, H.; Sturm, F.; Schmidt, L. P. H.; Schmidt-Bocking, H.; Dorner, R.; Stohner, J.; Kiedrowski, J.; Reggelin, M.; Marquardt, S.; Schiesser, A.; Berger, R.; Schoffler, M. S. (2013). "Direct Determination of Absolute Molecular Stereochemistry in Gas Phase by Coulomb Explosion Imaging" (PDF). Science. 341 (6150): 1096–1100. Bibcode:2013Sci...341.1096P. doi:10.1126/science.1240362. PMID 24009390. S2CID 206549826.
- ^ Crassous, J.; Collet, A. (2000). "The bromochlorofluoromethane saga". Enantiomer. 5 (5): 429–438. PMID 11143807.
- ^ Crassous, Jeanne; Monier, Franck; Dutasta, Jean-Pierre; Ziskind, Michaël; Daussy, Christophe; Grain, Christophe; Chardonnet, Christian (2003). "Search for Resolution of Chiral Fluorohalogenomethanes and Parity-Violation Effects at the Molecular Level". ChemPhysChem. 4 (6): 541–548. doi:10.1002/cphc.200200536. PMID 12836475.
- ^ Darquié, Benoît; Stoeffler, Clara; Shelkovnikov, Alexander; Daussy, Christophe; Amy-Klein, Anne; Chardonnet, Christian; Zrig, Samia; Guy, Laure; Crassous, Jeanne; Soulard, Pascale; Asselin, Pierre; Huet, Thérèse R.; Schwerdtfeger, Peter; Bast, Radovan; Saue, Trond (2010). "Progress toward the first observation of parity violation in chiral molecules by high-resolution laser spectroscopy". Chirality. 22 (10): 870–884. arXiv:1007.3352. doi:10.1002/chir.20911. PMID 20839292. S2CID 2722847.
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