Trichloroacetonitrile

Trichloroacetonitrile
Names
IUPAC name
Trichloroacetonitrile
Identifiers
545-06-2
3D model (Jmol) Interactive image
ECHA InfoCard 100.008.078
PubChem 24900271
Properties
C2Cl3N
Molar mass 144.38 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)
insoluble
Hazards
Main hazards GHS06, GHS09
Safety data sheet MSDS
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
4
0
Flash point 195 °C (383 °F; 468 K)
Except where otherwise noted, 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

  1. ↑ 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
  2. ↑ 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.
  3. ↑ "Overman Rearrangement". Organic Chemistry Portal. organic-chemistry.org. Retrieved November 15, 2012.
  4. ↑ 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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