phenyl chloromethanethioate

• ChemBase ID: 140273
• Molecular Formular: C7H5ClOS
• Molecular Mass: 172.632
• Monoisotopic Mass: 171.97496346
• SMILES: c1ccc(cc1)OC(=S)Cl
• Canonical SMILES: ClC(=S)Oc1ccccc1
• InChI: InChI=1S/C7H5ClOS/c8-7(10)9-6-4-2-1-3-5-6/h1-5H
• InChIKey: KOSYAAIZOGNATQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenyl chloromethanethioate
• IUPAC Traditional name: phenyl chloromethanethioate
• Synonyms: Carbonochloridothioic Acid O-Phenyl Ester; Chlorothioformic Acid O-Phenyl Ester; NSC 99103; O-Phenyl Carbonochloridothioate; O-Phenyl Chlorothiocarbonate; O-Phenyl Chlorothioformate; O-Phenyl Chlorothionoformate; Phenoxythiocarbonyl Chloride; Phenyl Chlorothiocarbonate; Phenyl Chlorothionoformate; Phenyl Thiochloroformate; Phenyl Thioxochloroformate; Phenyl Chlorothionoformate; Phenyl thionochloroformate; O-Phenyl chlorothionoformate; Phenyl chlorothionocarbonate; Phenyl chlorothionoformate; 氯甲基硫代苯酯; 硫代氯甲酸苯酯; 氯化硫代甲酸苯酯

Database IDs

• CAS Number: 1005-56-7
• EC Number: 213-736-4
• MDL Number: MFCD00004920
• Beilstein Number: 774830
• PubChem SID: 162234517; 24854046
• PubChem CID: 70498

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.477103
• LogD (pH = 7.4): 3.477103
• Log P: 3.477103
• Molar Refractivity: 45.8943 cm^3
• Polarizability: 18.151892 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Yellow Oil
• Boiling Point: 81-83 °C/6 mmHg(lit.); 81-83°C/6mm
• Flash Point: 177.8 °F; 81 °C; 81°C(177°F)
• Density: 1.248; 1.248 g/mL at 25 °C(lit.)
• Refractive Index: 1.5804; n20/D 1.581; n20/D 1.581(lit.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H227
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

Product Information

• Purity: ≥99.0% (AT); 98+%; 99%
• Grade: purum
• Linear Formula: ClC(S)OC6H5

DETAILS

Sigma Aldrich - 234524

Application
Reagent for thionocarbonylation of unprotected thymine nucleosides.1 Forms phenoxythiocarbonyl esters of protected ribonucleosides which can be reduced by tributyltin hydride (cat. no. 234788) to deoxyribonucleosides.2,3
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 26470

Other Notes
Reagent used for the Bu3SnH mediated deoxigenation of alcohols via thionocarbonates 1,2

Toronto Research Chemicals - P319650

Phenyl Chlorothionoformate is used in the preparation of an bicyclic thymidine analogs as selective inhibitors of Thymidine monophosphate kinase Mycobacterium tuberculosis (TMPKmt).

REFERENCES

• Vanheusden, V. et al.: J. Med. Chem., 47, 6187 (2004)
• 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).