Trichloroacetonitrile
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IUPAC name
Trichloroacetonitrile
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Identifiers | |
3D model (JSmol)
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ECHA InfoCard | 100.008.078 |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C2Cl3N | |
Molar mass | 144.38 g·mol−1 |
Appearance | colourless liquid |
Density | 1.44 g/mL |
Melting point | -42 |
insoluble | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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GHS06, GHS09 |
Flash point | 195 °C (383 °F) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
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: CS1 maint: multiple names: authors list (link) - ^ "Overman Rearrangement". Organic Chemistry Portal. organic-chemistry.org. Retrieved Novermber 15, 2012.
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(help) - ^ 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.