ブロモクロロフルオロメタン

ブロモクロロフルオロメタン
	優先IUPAC名 Bromo(chloro)fluoromethane
	別称 Bromochlorofluoromethane
識別情報
CAS登録番号	593-98-6;
3D model (JSmol)	Interactive image;
ChemSpider	71390 ;
PubChem CID	79058;
CompTox Dashboard (EPA)	DTXSID70870651 ;
	InChI InChI=1S/CHBrClF/c2-1(3)4/h1H Key: YNKZSBSRKWVMEZ-UHFFFAOYSA-N ;
	SMILES C(F)(Cl)Br;
特性
化学式	CHBrClF
モル質量	147.37 g mol−1
密度	1.953 g/cm3
融点	-115 °C, 158 K, -175 °F
沸点	36 °C, 309 K, 97 °F
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

ブロモクロロフルオロメタン(英語: Bromochlorofluoromethaneは分子式CHFClBrで表されるトリハロメタンである。もっとも単純で、かつ安定に存在するキラル化合物であり、キラル化学の基礎研究に用いられている^[1]。現在では多くの分離法が存在するが、最初に合成されてから１世紀近くもの間、エナンチオマー同士の分離に成功しなかった^[2]^[3]^[4]^[5]^[6]^[7]。また、最新の量子力学の研究においてはパリティ対称性の破れの観測実験に使われている^[8]^[9]^[10]。

脚注

[脚注の使い方]

^ Berry, Kenneth L.; Sturtevant, Julian M. (1942). “Fluorochlorobromomethane”. Journal of the American Chemical Society 64 (7): 1599–1600. doi:10.1021/ja01259a031.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Pitzer, M.; Kunitski, M.; Johnson, A. S.; Jahnke, T.; Sann, H.; Sturm, F.; Schmidt, L. P. H.; Schmidt-Bocking, H. et al. (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.
^ Crassous, J.; Collet, A. (2000). “The bromochlorofluoromethane saga”. Enantiomer 5 (5): 429–438. PMID 11143807.
^ 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.
^ Darquié, Benoît; Stoeffler, Clara; Shelkovnikov, Alexander; Daussy, Christophe; Amy-Klein, Anne; Chardonnet, Christian; Zrig, Samia; Guy, Laure et al. (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.

[1] Berry, Kenneth L.; Sturtevant, Julian M. (1942). “Fluorochlorobromomethane”. Journal of the American Chemical Society 64 (7): 1599–1600. doi:10.1021/ja01259a031.

[2] 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.

[3] 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.

[4] 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.

[5] 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.

[6] 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.

[7] Pitzer, M.; Kunitski, M.; Johnson, A. S.; Jahnke, T.; Sann, H.; Sturm, F.; Schmidt, L. P. H.; Schmidt-Bocking, H. et al. (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.

[8] Crassous, J.; Collet, A. (2000). “The bromochlorofluoromethane saga”. Enantiomer 5 (5): 429–438. PMID 11143807.

[9] 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.

[10] Darquié, Benoît; Stoeffler, Clara; Shelkovnikov, Alexander; Daussy, Christophe; Amy-Klein, Anne; Chardonnet, Christian; Zrig, Samia; Guy, Laure et al. (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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

ブロモクロロフルオロメタン

脚注

Portal di Ensiklopedia Dunia