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237582

Sigma-Aldrich

Methyl 2-phenylsulfinylacetate

98%

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About This Item

Linear Formula:
C6H5S(O)CH2CO2CH3
CAS Number:
14090-83-6
Molecular Weight:
198.24
Beilstein/REAXYS Number:
1953383
EC Number:
237-936-6
MDL number:
MFCD00002087
UNSPSC Code:
12352100
PubChem Substance ID:
24854255
NACRES:
NA.22

assay

98%

form

solid

bp

130-131 °C/0.5 mmHg (lit.)

mp

52-54 °C (lit.)

SMILES string

COC(=O)CS(=O)c1ccccc1

InChI

1S/C9H10O3S/c1-12-9(10)7-13(11)8-5-3-2-4-6-8/h2-6H,7H2,1H3

InChI key

JPPXZUDQIXZLIL-UHFFFAOYSA-N

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General description

Anion of methyl 2-phenylsulfinylacetate undergoes facile alkylative elimination under solid-liquid phase-transfer conditions to afford ring-substituted cinnamates[1]. Methyl 2-phenylsulfinylacetate undergoes condensation reactions with aldehydes to form vinylic sulfoxides[2].

Application

Anion of methyl 2-phenylsulfinylacetate has been employed in the synthesis of α,β-unsaturated esters[3].

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP1668V
07315BE
09915ER
06006MF
10025EU

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Journal of the Chemical Society. Perkin Transactions 1, 2683-2683 (1991)
New Synthetic reactions. Alkylative elimination.
Trost BM, et al.
Journal of the American Chemical Society, 96(22), 7165-7167 (1974)
Phase-Transfer Catalyzed Alkylative Elimination of Methyl 2-Phenylsulfinylacetate. A One-Pot Synthesis of Substituted Cinnamates.
Chong-ying X, et al.
Synthetic Communications, 17(15), 1839-1843 (1987)

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