Bromochlorofluoromethane

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][8] More recent research using bromochlorofluoromethane has focused on its potential use for experimental measurement of parity violation, a major unsolved problem in quantum physics.[9][10][11]

Bromochlorofluoromethane
Names
Preferred IUPAC name
Bromo(chloro)fluoromethane
Other names
Bromochlorofluoromethane
Identifiers
3D model (JSmol)
ChemSpider
UNII
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).
Infobox references

See also

References
  1. Berry, Kenneth L.; Sturtevant, Julian M. (1942). "Fluorochlorobromomethane". Journal of the American Chemical Society. 64 (7): 1599–1600. doi: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. ISBN 0-08-042704-9
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. Polavarapu, Prasad L. (2002). "The Absolute Configuration of Bromochlorofluoromethane". Angewandte Chemie International Edition. 41 (23): 4544–4546. doi:10.1002/1521-3773(20021202)41:23<4544::aid-anie4544>3.0.co;2-s. PMID 12458533.
  8. 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". Science. 341 (6150): 1096–1100. Bibcode:2013Sci...341.1096P. doi:10.1126/science.1240362. PMID 24009390.
  9. Crassous, J.; Collet, A. (2000). "The bromochlorofluoromethane saga". Enantiomer. 5 (5): 429–438. PMID 11143807.
  10. 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.
  11. 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.
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