Bromochlorofluoromethane

Bromochlorofluoromethane
Names
Preferred IUPAC name
Bromo(chloro)fluoromethane
Other names
Bromochlorofluoromethane
Identifiers
593-98-6
3D model (Jmol) Interactive image
ChemSpider 71390 YesY
PubChem 79058
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

Bromochlorofluoromethane or fluorochlorobromomethane, is a chemical compound and trihalomethane deriative 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]

See also

References

  1. ↑ Kenneth L. Berry and Julian M. Sturtevant. Fluorochlorobromomethane. Journal of the American Chemical Society 1942; 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. ↑ Michael K. Hargreaves and Borzoo Modarai. An optically active haloform: (+)-bromochlorofluoromethane. J. Chem. Soc. D; 1969: 16-16. DOI: 10.1039/C29690000016
  4. ↑ Canceill J, Lacombe L, Collet A. Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailor-made cryptophane and determination of its maximum rotation. J Am Chem Soc 1985; 107: 6993–6996.
  5. ↑ Doyle TR, Vogl O. Bromochlorofluoromethane and deuteriobromochlorofluoromethane of high optical purity. J. Am. Chem. Soc. 1989; 111(22):8510–8511. DOI: 10.1021/ja00204a029
  6. ↑ Heiko Grosenick, Volker Schurig, Jeanne Costante, André Collet. Gas chromatographic enantiomer separation of bromochlorofluoromethane. Tetrahedron: Asymmetry January 1995; 6(1):87–88. doi:10.1016/0957-4166(94)00358-I
  7. ↑ Polavarapu PL. The absolute configuration of bromochlorofluoromethane. Angew Chem Int Ed Engl. 2002 Dec 2;41(23):4544-6. PMID 12458533
  8. ↑ Pitzer M, Kunitski M, Johnson AS, Jahnke T, Sann H, Sturm F, Schmidt LP, Schmidt-Böcking H, Dörner R, Stohner J, Kiedrowski J, Reggelin M, Marquardt S, Schießer A, Berger R, Schöffler MS. Direct determination of absolute molecular stereochemistry in gas phase by Coulomb explosion imaging. Science. 2013 Sep 6;341(6150):1096-100. doi: 10.1126/science.1240362 PMID 24009390
  9. ↑ Crassous J, Collet A. The bromochlorofluoromethane saga. Enantiomer. 2000;5(5):429-38. PMID 11143807
  10. ↑ Crassous J, Monier F, Dutasta JP, Ziskind M, Daussy C, Grain C, Chardonnet C. Search for resolution of chiral fluorohalogenomethanes and parity-violation effects at the molecular level. Chemphyschem. 2003 Jun 16;4(6):541-8. PMID 12836475
  11. ↑ Darquié B, Stoeffler C, Shelkovnikov A, Daussy C, Amy-Klein A, Chardonnet C, Zrig S, Guy L, Crassous J, Soulard P, Asselin P, Huet TR, Schwerdtfeger P, Bast R, Saue T. Progress toward the first observation of parity violation in chiral molecules by high-resolution laser spectroscopy. Chirality. 2010 Nov;22(10):870-84. doi: 10.1002/chir.20911 PMID 20839292
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