Bromochlorofluoromethane Explained

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]}

See also

• Bromochlorodifluoromethane, used in fire extinguishers
• Bromochlorofluoroiodomethane, a theoretical derivative with iodine replacing the hydrogen

Notes and References

1. Berry. Kenneth L.. Sturtevant. Julian M.. Fluorochlorobromomethane. Journal of the American Chemical Society. 1942. 64. 7. 1599–1600. 10.1021/ja01259a031.
2. Thomas L. Gilchrist. Comprehensive Organic Functional Group Transformations. Volume 6. Synthesis: Carbon with Three or Four Attached Heteroatoms. p228. Pergamon / Elsevier, 1995.
3. Hargreaves. Michael K.. Modarai. Borzoo. An optically active haloform: (+)-bromochlorofluoromethane. Journal of the Chemical Society D: Chemical Communications. 1969. 1. 16. 10.1039/C29690000016.
4. Canceill. Josette. Lacombe. Liliane. Collet. Andre. 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. 1985. 107. 24. 6993–6996. 10.1021/ja00310a041.
5. Doyle. Thomas R.. Vogl. Otto. Bromochlorofluoromethane and deuteriobromochlorofluoromethane of high optical purity. Journal of the American Chemical Society. 1989. 111. 22. 8510–8511. 10.1021/ja00204a029.
6. Grosenick. Heiko. Schurig. Volker. Costante. Jeanne. Collet. André. Gas chromatographic enantiomer separation of bromochlorofluoromethane. Tetrahedron: Asymmetry. 1995. 6. 1. 87–88. 10.1016/0957-4166(94)00358-I.
7. 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.. Direct Determination of Absolute Molecular Stereochemistry in Gas Phase by Coulomb Explosion Imaging. Science. 2013. 341. 6150. 1096–1100. 10.1126/science.1240362. 24009390. 2013Sci...341.1096P. 206549826 .
8. Crassous . J.. Jeanne Crassous. Collet. A. . The bromochlorofluoromethane saga. Enantiomer. 2000. 5. 5. 429–438. 11143807.
9. Crassous. Jeanne. Monier. Franck. Dutasta. Jean-Pierre. Ziskind. Michaël. Daussy. Christophe. Grain. Christophe. Chardonnet. Christian. Search for Resolution of Chiral Fluorohalogenomethanes and Parity-Violation Effects at the Molecular Level. ChemPhysChem. 2003. 4. 6. 541–548. 10.1002/cphc.200200536. 12836475.
10. 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. Progress toward the first observation of parity violation in chiral molecules by high-resolution laser spectroscopy. Chirality. 2010. 22. 10. 870–884. 10.1002/chir.20911. 20839292. 1007.3352. 2722847 .