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(S)-methyl thiobenzoate

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(S)-methyl thiobenzoate Basic information

Product Name:
(S)-methyl thiobenzoate
Synonyms:
  • (S)-methyl thiobenzoate
  • Benzenecarbothioic acid, S-methyl ester
  • S-METHYL-BENZOTHIOATE
  • METHYLSULFANYL-PHENYL-METHANONE
  • Thiobenzoic acid S-methyl ester
  • Einecs 227-656-2
  • S-Ethyl benzothioate
  • S-methylbenzenecarbothioate
CAS:
5925-68-8
MF:
C8H8OS
MW:
152.21
EINECS:
227-656-2
Mol File:
5925-68-8.mol
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(S)-methyl thiobenzoate Chemical Properties

Boiling point:
134 °C(Press: 25 Torr)
Density 
1.1381 g/cm3(Temp: 25 °C)
FEMA 
3857 | S-METHYL BENZOTHIOATE
Odor
at 0.10 % in propylene glycol. sulfurous cabbage garlic potato vegetable
Odor Type
sulfurous
JECFA Number
504
LogP
2.23
CAS DataBase Reference
5925-68-8
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(S)-methyl thiobenzoate Usage And Synthesis

Definition

ChEBI: S-Methyl benzenecarbothioate is a member of benzoic acids.

Synthesis Reference(s)

[1] Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds. J. Org. Chem. 2020, 85, 22, 14653–14663.

Synthesis

A mixture of a well-powdered benzoic anhydride (6.0 mmol), thiourea (6.5 mmol), and Et3N (2.5 mL) was stirred at 40 °C until the starting anhydride was completely consumed and a two-phase system containing Et3N and a thick brick-red liquid was formed. Then, water (5.0 mL) and CH3I (5.0 mmol) were added to the mixture, and stirring was continued at room temperature. After consumption of starting CH3I (3 h), the crude product was extracted with EtOAc (15 mL × 2). The crude product was purified by column chromatography over silica gel (300–400 mesh) using petroleum ether/ethyl acetate as an eluent to give analytically pure product (S)-methyl thiobenzoate.

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