trichloroacetonitrile

• ChemBase ID: 89276
• Molecular Formular: C2Cl3N
• Molecular Mass: 144.3871
• Monoisotopic Mass: 142.90963205
• SMILES: N#CC(Cl)(Cl)Cl
• Canonical SMILES: N#CC(Cl)(Cl)Cl
• InChI: InChI=1S/C2Cl3N/c3-2(4,5)1-6
• InChIKey: DRUIESSIVFYOMK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trichloroacetonitrile
• IUPAC Traditional name: trichloroacetonitrile
• Synonyms: 2,2,2-trichloroacetonitrile; Trichloromethyl cyanide; Trichloroacetonitrile 96%; Trichloroacetonitrile; Trichloroacetonitrile; 三氯乙腈

Database IDs

• CAS Number: 545-06-2
• EC Number: 208-885-7
• MDL Number: MFCD00001842
• Beilstein Number: 605572
• Merck Index: 149628
• PubChem SID: 24867685; 24900271; 24889442; 162076157
• PubChem CID: 11011; 24900271
• Wikipedia Title: Trichloroacetonitrile

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5869915
• LogD (pH = 7.4): 1.5869915
• Log P: 1.5869915
• Molar Refractivity: 27.1376 cm^3
• Polarizability: 10.134492 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: insoluble in water
• Apperance: colourless liquid
• Melting Point: -42; -42°C; -44°C
• Boiling Point: 83 - 84°C; 83-84 °C(lit.); 83-84°C; 85-86°C
• Flash Point: 195 °C; 195°C (383°F); 383 °F
• Density: 1.44; 1.44 g/mL; 1.44 g/mL at 25 °C(lit.)
• Refractive Index: 1.4410; 1.4840; n20/D 1.441; n20/D 1.441(lit.)
• Vapor Pressure: 58 mmHg ( 20 °C)

Safety Information

• Storage Warning: Toxic/Lachrymatory
• RTECS: AM2450000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3276; UN3276
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 23/24/25-51/53
• Safety Statements: 45-61
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• Main Hazard: GHS06, GHS09
• GHS Hazard statements: H301-H311-H331-H411
• GHS Precautionary statements: P261-P273-P280-P301 + P310-P311; P261-P301+P310-P361-P302+P352-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3276 6.1/PG 3

Product Information

• Purity: ≥95.0% (GC); 98%
• Grade: analytical standard; purum
• Packaging: ampule of 1000 mg
• Linear Formula: Cl3CCN

DETAILS

Sigma Aldrich - T53805

Application
Employed in a synthesis of trichloroacetimidates by DBU catalyzed addition of allylic alcohols and the subsequent study of the MOM catalyzed aza-Claisen rearrangement.1 Also used to prepare bistrichloroacetimidates from diols leading to dihyrooxazines via acid catalyzed cyclization.2
Packaging
5, 100, 500 g in glass bottle

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).