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氟氯溴甲烷

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氟氯溴甲烷
IUPAC名
Bromo(chloro)fluoromethane
别名 Bromochlorofluoromethane
识别
CAS号 593-98-6
PubChem 79058
ChemSpider 71390
SMILES
 
  • C(F)(Cl)Br
InChI
 
  • InChI=1S/CHBrClF/c2-1(3)4/h1H
InChIKey YNKZSBSRKWVMEZ-UHFFFAOYSA-N
性质
化学式 CHBrClF
摩尔质量 147.37 g·mol−1
密度 1.953 g/cm3
熔点 -115 °C（158 K）
沸点 36 °C（309 K）
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

溴氯氟甲烷（英语：Bromochlorofluoromethane）或氟氯溴甲烷（fluorochlorobromomethane）是一种化合物，是一种三卤甲烷衍生物，化学式是CHBrClF。作为一种最简单的可能的稳定的手性化合物，它对于化学的手性化合物领域的基本研究十分有用。[1] 然而，其水解的相对不稳定[2] 和缺乏适当的官能团，使得分离溴氯氟甲烷的对映异构体尤其具有挑战性，[3] 尽管现在它已经可以通过各种各样的方法分离，这一过程直到它被第一次合成一个世纪后的2005年才完成。[4][5][6][7][8] 更多的使用溴氯氟甲烷的近期研究关注于它的潜在用途——用于奇偶校验违反的实验测量，量子力学的一个主要的未解决的问题。[9][10][11]

参见

参考文献

  1. ^ Berry, Kenneth L.; Sturtevant, Julian M. 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. ^ Hargreaves, Michael K.; Modarai, Borzoo. An optically active haloform: (+)-bromochlorofluoromethane. Journal of the Chemical Society D: Chemical Communications. 1969, 1: 16. doi: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. doi: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. doi: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. doi:10.1016/0957-4166(94)00358-I. 
  7. ^ Polavarapu, Prasad L. The Absolute Configuration of Bromochlorofluoromethane. Angewandte Chemie International Edition. 2002, 41 (23): 4544–4546. PMID 12458533. doi:10.1002/1521-3773(20021202)41:23<4544::aid-anie4544>3.0.co;2-s. 
  8. ^ Pitzer, M.; Kunitski, M.; Johnson, A. S.; Jahnke, T.; Sann, H.; Sturm, F.; Schmidt, L. P. H.; Schmidt-Bocking, H.; Dorner, R. Direct Determination of Absolute Molecular Stereochemistry in Gas Phase by Coulomb Explosion Imaging. Science. 2013, 341 (6150): 1096–1100. Bibcode:2013Sci...341.1096P. PMID 24009390. doi:10.1126/science.1240362. 
  9. ^ Crassous, J.; Collet, A. The bromochlorofluoromethane saga. Enantiomer. 2000, 5 (5): 429–438. PMID 11143807. 
  10. ^ 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. PMID 12836475. doi:10.1002/cphc.200200536. 
  11. ^ Darquié, Benoît; Stoeffler, Clara; Shelkovnikov, Alexander; Daussy, Christophe; Amy-Klein, Anne; Chardonnet, Christian; Zrig, Samia; Guy, Laure; Crassous, Jeanne. Progress toward the first observation of parity violation in chiral molecules by high-resolution laser spectroscopy. Chirality. 2010, 22 (10): 870–884. PMID 20839292. arXiv:1007.3352 可免费查阅. doi:10.1002/chir.20911. 
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