氟氯溴甲烷
溴氯氟甲烷（英語：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]
| 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 |
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| InChI |
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| 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。 | |
参见 编辑
参考文献 编辑
- ^ Berry, Kenneth L.; Sturtevant, Julian M. Fluorochlorobromomethane. Journal of the American Chemical Society. 1942, 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. An optically active haloform: (+)-bromochlorofluoromethane. Journal of the Chemical Society D: Chemical Communications. 1969, 1: 16. doi:10.1039/C29690000016.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Crassous, J.; Collet, A. The bromochlorofluoromethane saga. Enantiomer. 2000, 5 (5): 429–438. PMID 11143807.
- ^ 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.
- ^ 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
. doi:10.1002/chir.20911.
