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234184

Sigma-Aldrich

Methyl phenylsulfonylacetate

97%

Synonym(s):
Methyl benzenesulfonylacetate
Linear Formula:
C6H5SO2CH2COOCH3
CAS Number:
Molecular Weight:
214.24
Beilstein:
2051463
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.535 (lit.)

bp

165 °C/0.05 mmHg (lit.)

density

1.305 g/mL at 20 °C (lit.)

SMILES string

COC(=O)CS(=O)(=O)c1ccccc1

InChI

1S/C9H10O4S/c1-13-9(10)7-14(11,12)8-5-3-2-4-6-8/h2-6H,7H2,1H3

InChI key

NLEAIFBNKPYTGN-UHFFFAOYSA-N

Gene Information

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Application

Methyl phenylsulfonylacetate has been used:
  • in a key step during the synthesis of (−)-hybridalactone, marine eicosanoid isolated from the red alga Laurencia hybrida
  • in dehydrative alkylation of alcohols under modified Mitsunobu conditions followed by desulfonylation using magnesium
  • in three step synthesis of 2-(hydroxymethyl)indene

Packaging

10 g in glass bottle

Certificate of Analysis

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Certificate of Origin

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An improved synthesis of 2-(hydroxymethyl) indene.
Palandoken H, et al.
Organic Prep. and Proc. Int., 28(6), 702-704 (1996)
Methyl Carboxymethylenation of Alcohols via Dehydrative Alkylation.
YuJ, et al.
Synlett, 1995(11), 1127-1128 (1995)
Koichiro Ota et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(42), 13531-13537 (2012-09-12)
(-)-Hybridalactone (1) is a marine eicosanoid isolated from the red alga Laurencia hybrida. This natural product contains cyclopropane, cyclopentane, 13-membered macrolactone and epoxide ring systems incorporating seven stereogenic centers. Moreover, this compound has an acid-labile skipped Z,Z-diene motif. In this

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