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Trichloroacetonitrile information


Trichloroacetonitrile
Names
Preferred IUPAC name
Trichloroacetonitrile
Other names
trichlorocyanomethane, trichloroethanenitrile, cyanochloroform, trichloromethyl cyanide, trichloroethyl nitrile
Identifiers
CAS Number
  • 545-06-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 13861934
ECHA InfoCard 100.008.078 Edit this at Wikidata
PubChem CID
  • 24900271
UNII
  • 6397DL8869 checkY
CompTox Dashboard (EPA)
  • DTXSID0021672 Edit this at Wikidata
InChI
  • InChI=1S/C2Cl3N/c3-2(4,5)1-6
    Key: DRUIESSIVFYOMK-UHFFFAOYSA-N
SMILES
  • ClC(Cl)(Cl)C#N
Properties
Chemical formula
C2Cl3N
Molar mass 144.38 g·mol−1
Appearance colourless liquid
Density 1.44 g/mL
Melting point −42 °C (−44 °F; 231 K)
Boiling point 83 to 84 °C (181 to 183 °F; 356 to 357 K)
Solubility in water
insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
GHS06, GHS09
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Flash point 195 °C (383 °F; 468 K)
Safety data sheet (SDS) MSDS
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] As a bifunctional compound, trichloroacetonitrile can react at both the trichloromethyl and the nitrile group. The electron-withdrawing effect of the trichloromethyl group activates the nitrile group for nucleophilic additions. The high reactivity makes trichloroacetonitrile a versatile reagent, but also causes its susceptibility towards hydrolysis.

  1. ^ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2002). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 978-3527306732.

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Trichloroacetonitrile

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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...

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Acetonitrile

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main pathways of excretion are by exhalation and in the urine. Trichloroacetonitrile – a derivative of acetonitrile used to protect alcohol groups, and...

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Acyl azide

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carboxylic acids and sodium azide in presence of triphenylphosphine and trichloroacetonitrile catalysts in excellent yields at mild conditions. Another route...

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Tetraazidomethane

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groups. It was first prepared by Klaus Banert in 2006 by reaction of trichloroacetonitrile with sodium azide. As with other polyazides, tetraazidomethane has...

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Trifluoroacetonitrile

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compounds Related compounds acetonitrile trifluoromethylisocyanide trichloroacetonitrile Except where otherwise noted, data are given for materials in their...

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Carboximidate

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For example, the base catalyzed reaction of benzyl alcohol upon trichloroacetonitrile yields a trichloroacetimidate. This species has orthogonal stability...

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Ethyl trifluoroacetate

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in turn, can be prepared by a two-step reaction starting from trichloroacetonitrile by reaction with hydrogen chloride and fluorination of the intermediate...

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IARC group 3

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fusarenone X) Toxins derived from Fusarium sporotrichioides Trichlorfon Trichloroacetonitrile 1,1,2-Trichloroethane Triethanolamine Triethylene glycol diglycidyl...

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Chemical glycosylation

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O-Glycosyl trichloroacetimidates are prepared via the addition of trichloroacetonitrile (Cl 3CCN) under basic conditions to a free anomeric hydroxyl group...

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Tetramethoxymethane

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and chlorine) was used: A less problematic synthesis is based on trichloroacetonitrile, with yields of about 70% be achieved: Further preparative methods...

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List of compounds with carbon number 2

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dichlorodifluoroethylene 27156-03-2 C2Cl2O2 oxalyl chloride 79-37-8 C2Cl3N trichloroacetonitrile 108-77-0 C2Cl4 tetrachloroethylene 127-18-4 C2Cl4O trichloroacetyl...

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Tetraethoxymethane

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the homologous tetramethoxymethane. Starting from the less toxic trichloroacetonitrile (compared with trichloronitromethane), higher yields can be obtained...

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Homoleptic azido compounds

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carbontetrahalides and instead can be obtained via a reaction of trichloroacetonitrile Cl3CCN with NaN3 albeit in relatively low yields. Yields can be...

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