氟氯溴甲烷

溴氯氟甲烷（英語：Bromochlorofluoromethane）或氟氯溴甲烷（fluorochlorobromomethane）是一種化合物，是一種三鹵甲烷衍生物，化學式是CHBrClF。作為一種最簡單的可能的穩定的手性化合物，它對於化學的手性化合物領域的基本研究十分有用。^[1] 然而，其水解的相對不穩定^[2] 和缺乏適當的官能團，使得分離溴氯氟甲烷的對映異構體尤其具有挑戰性，^[3] 儘管現在它已經可以通過各種各樣的方法分離，這一過程直到它被第一次合成一個世紀後的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關注於它的潛在用途——用於奇偶校驗違反的實驗測量，量子力學的一個主要的未解決的問題。^[9][10][11]

氟氯溴甲烷
IUPAC名 Bromo(chloro)fluoromethane
別名	Bromochlorofluoromethane
識別
CAS號	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
性質
化學式	CHBrClF
摩爾質量	147.37 g·mol−1
密度	1.953 g/cm3
熔點	-115 °C（158 K）
沸點	36 °C（309 K）
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

參見

• 二氟一氯一溴甲烷，在滅火器中使用
• 氟氯溴碘化碳，一理論上的碘替代氫的衍生物

參考文獻

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 . doi:10.1002/chir.20911.