Phenyl chlorothionoformate

• Catalog No.: L00838
• CAS Number: 1005-56-7
• M. F.: C7H5ClOS
• M. W.: 172.632
• Purity: 98+%

SYNONYMS

• Title: 氯化硫代甲酸苯酯
• IUPAC name: phenyl chloromethanethioate
• IUPAC Traditional name: phenyl chloromethanethioate
• Synonyms: Phenyl chlorothionocarbonate; Phenyl thionochloroformate

DATABASE IDS

• MDL Number: MFCD00004920
• EC Number: 213-736-4
• CAS Number: 1005-56-7
• Beilstein Number: 774830

PROPERTIES

• Purity: 98+%
• Boiling Point: 81-83°C/6mm
• Density: 1.248
• Flash Point: 81°C(177°F)
• Refractive Index: 1.5804
• GHS Hazard statements: H314-H318-H227
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P280-P305+P351+P338-P309-P310
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3265
• Packing Group: II

REFERENCES

• Similarly, amides are dehydrated to nitriles, and formamides to isonitriles under mild conditions: Tetrahedron Lett., 40, 747 (1999).
• Aryl chlorothionoformates react with OH groups to give thiocarbonate esters. These have a much greater tendency to undergo cyclic elimination than their oxygen counterparts, with dehydration as the net result. Thus, e.g. oximes are dehydrated to nitriles under mild conditions: Chem. Commun., 1014 (1970):
  
• Alcohols are converted to alkenes in better yields than in the Chugaev (xanthate pyrolysis) method, succeeding with hindered alcohols which do not readily form xanthates: J. Chem. Soc., Chem. Commun., 1215 (1972); Helv. Chim. Acta, 55, 2277 (1972). Secondary alcohols give thiocarbonate esters which can be reduced to alkanes by tributyltin hydride, in a useful deoxygenation sequence. For use in an enantiospecific synthesis of the antiviral agent ganciclovir phosphonate, see: J. Med. Chem., 37, 1371 (1994).
• Reagent for conversion of imidazoles to imidazole-2-thiones: Synlett, 239 (1995).
• Reagent, alternative to chloroformates, for dealkylation of tertiary amines: Austral. J. Chem., 52, 841 (1999).