Trichloroacetonitrile
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| Trichloroacetonitrile | ||
|---|---|---|
 | ||
| IUPAC name Trichloroacetonitrile | ||
| Identifiers | ||
| CAS number | 545-06-2 | |
| PubChem | 24900271 | |
| Jmol-3D images | Image 1 | |
| ||
| Properties | ||
| Molecular formula | C2Cl3N | |
| Molar mass | 144.39 g mol−1 | |
| Appearance | colourless liquid | |
| Density | 1.44 g/mL | |
| Melting point | -42 | |
| Boiling point | 83 to 84 °C; 181 to 183 °F; 356 to 357 K | |
| Solubility in water | insoluble | |
| Hazards | ||
| MSDS | MSDS | |
| Main hazards | GHS06, GHS09 | |
| Flash point | 195 °C; 383 °F; 468 K | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Trichloroacetonitrile is an organic compound with the formula CCl3CN. It is a colourless liquid, although commercial samples often are brownish. It is used commercially as a precursor to the fungicide etridiazole. It is prepared by dehydration of trichloroacetamide.[1]
In academic research, trichloroacetonitrile is used as a reagent in the Overman rearrangement, converting allylic alcohols into allylic amines.[2][3][4]
See also
References
- ↑ Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363
- ↑ T. Nishikawa, M. Asai, N. Ohyabu, M. Isobe (1998). "Improved Conditions for Facile Overman Rearrangement(1)". J. Org. Chem. 63 (1): 188–192. doi:10.1021/jo9713924. PMID 11674062.
- ↑ "Overman Rearrangement". Organic Chemistry Portal. organic-chemistry.org. Retrieved November 15, 2012.
- ↑ Y. K. Chen. A. E. Lurain, P. J. Walsh (2002). "A general, highly enantioselective method for the synthesis of D and L alpha-amino acids and allylic amines". J. Am. Chem. Soc. 124 (41): 12225–12231. doi:10.1021/ja027271p. PMID 12371863.
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