Trichloroacetonitrile

• Catalog No.: A10565
• CAS Number: 545-06-2
• M. F.: C2Cl3N
• M. W.: 144.3871
• Purity: 98%

SYNONYMS

• Title: 三氯乙腈
• IUPAC name: trichloroacetonitrile
• IUPAC Traditional name: trichloroacetonitrile

DATABASE IDS

• MDL Number: MFCD00001842
• Beilstein Number: 605572
• Merck Index: 149628
• CAS Number: 545-06-2
• EC Number: 208-885-7

PROPERTIES

• Purity: 98%
• Boiling Point: 85-86°C
• Density: 1.44
• Melting Point: -44°C
• Refractive Index: 1.4410
• GHS Hazard statements: H301-H311-H331-H411
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P261-P301+P310-P361-P302+P352-P405-P501A
• Risk Statements: 23/24/25-51/53
• RTECS: AM2450000
• Safety Statements: 45-61
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN3276
• Packing Group: III

REFERENCES

• The combination with PPh₃ is superior to the popular CCl₄-PPh₃ system for conversion of carboxylic acids to acyl chlorides: Tetrahedron Lett., 40, 5323 (1999). It also converts allylic alcohols to the corresponding chlorides: Russ. J. Org. Chem., 31, 1019 (1995).
• In the presence of a base, e.g DBU, reacts with alcohols to form trichloroacetimidates, which are a useful means of protection, readily cleaved by TsOH/MeOH, DBU/MeOH or Zn/NH₄Cl: Synlett, 753(1999). These imidates are activated towards displacement by nucleophiles. Glycosyl imidates, formed in the presence of a base such as K₂CO₃ or DBU, are widely applied as glycosyl donors in oligosaccharide synthesis. Reaction with the free OH of the glycosyl acceptor occurs under mild conditions, promoted by a Lewis acid, e.g. BF₃ etherate or TMS-OTf, to form, respectively, either the ?- or ɑ-glycoside as the major product: Angew. Chem. Int. Ed., 25, 212 (1986). For reviews, see: Chem. Rev., 93, 1503 (1993); Adv. Carbohydr. Chem. Biochem., 50, 21 (1994); Contemp. Org. Synth., 3, 173 (1996). The imidates of allylic alcohols, prepared using NaH, or, more conveniently, KOH under phase-transfer conditions: Tetrahedron Lett., 37, 1481 (1996), undergo a [3,3]-sigmatropic rearrangement to derivatives of allylamines: J. Am. Chem. Soc., 96, 597 (1974); 98, 2901 (1976). For an example, see: Org. Synth. Coll., 6, 507 (1988). Review: Acc. Chem. Res., 13, 218 (1980):
  
• Reacts with hydrogen peroxide, to give, in situ, peroxytrichloroacetamidic acid, a reagent for the epoxidation of alkenes under essentially neutral conditions: J. Org. Chem., 48, 888 (1983).
• Aromatic aldoximes are dehydrated to nitriles by a similar cyclic mechanism: J. Org. Chem., 38, 2241 (1973).
• For a review of the chemistry of trichloroacetonitrile, see: Heterocycles, 43, 1083 (1996).