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1005-56-7 - Phenyl chlorothionoformate, 98+% - Phenyl chlorothionocarbonate - Phenyl thionochloroformate - L00838 - Alfa Aesar

L00838 Phenyl chlorothionoformate, 98+%

CAS Number
1005-56-7
Synonyms
Phenyl chlorothionocarbonate
Phenyl thionochloroformate

Size Price ($) Quantity Availability
1g 23.22
5g 69.83
25g 264.60
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Phenyl chlorothionoformate, 98+%

MDL
MFCD00004920
EINECS
213-736-4

Chemical Properties

Formula
C7H5ClOS
Formula Weight
172.63
Boiling Point
81-83°/6mm
Flash Point
81°(177°F)
Density
1.248
Refractive Index
1.5804
Sensitivity
Moisture Sensitive
Solubility
Soluble in water.

Applications

Phenyl chlorothionoformate has been used in stereo directed synthesis of optically active, (-)-mintlactone, synthesis of peptide α-thioesters having a variety of C-terminal amino acids, synthesis of scyllo-inositol derivatives, thionocarbonylation of unprotected thymine nucleosides, preparation of phenoxythiocarbonyl esters of protected ribonucleosides. It is also used as a reagent in the thionocarbonylation of unprotected thymine nucleosides. It forms phenoxythiocarbonyl esters of protected ribonucleosides which can be reduced by tributyltin hydride to deoxyribonucleosides.

Notes

Moisture, Heat Sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Keep away from oxidizing agents. Stable under recommended storage conditions.

Literature References

DN Kevill.; MJ D'Souza. Correlation of the rates of solvolysis of phenyl chlorothionoformate and phenylchlorodithioformate. Canadian journal of chemistry. 199977(5-6) , 1118-1122.

DS Millan.; RH Prager. The dealkylation of tertiary aliphatic amines with phenyl chlorothionoformate. Tetrahedron letters. 199839(24) , 4387-4390.

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):

Similarly, amides are dehydrated to nitriles, and formamides to isonitriles under mild conditions: Tetrahedron Lett., 40, 747 (1999).

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H227

Causes severe skin burns and eye damage. Causes serious eye damage. Combustible liquid.

Precautionary Statements: P280-P305+P351+P338-P309-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
774830
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2930.90
TSCA
No

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