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339997

Sigma-Aldrich

(S)-(−)-Methyl p-tolyl sulfoxide

99%

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About This Item

Linear Formula:
CH3C6H4S(O)CH3
CAS Number:
5056-07-5
Molecular Weight:
154.23
Beilstein/REAXYS Number:
2324696
MDL number:
MFCD00151503
UNSPSC Code:
12191600
PubChem Substance ID:
24860755
NACRES:
NA.22

assay

99%

form

solid

optical activity

[α]20/D −145°, c = 2 in acetone

optical purity

ee: 99% (HPLC)

mp

75-77 °C (lit.)

SMILES string

Cc1ccc(cc1)S(C)=O

InChI

1S/C8H10OS/c1-7-3-5-8(6-4-7)10(2)9/h3-6H,1-2H3/t10-/m0/s1

InChI key

FEVALTJSQBFLEU-JTQLQIEISA-N

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Application

(S)-(-)-Methyl p-tolyl sulfoxide can be used as a nucleophilic reagent to synthesize:
  • Optically active β-disulfoxides by reacting with arenesulfinic esters via formation of α-sulfinylcarbanion.
  • α-substituted N-hydroxylamines by treating with nitrones via preparation of (S)-(-)-methyl p-tolyl sulfoxide anion.
  • 2-O-benzyl-3,4-O-isopropylidene-L-erythrose by one-carbon homologation of 2,3-O-isopropylidene-L-glyceraldehyde.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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β -Disulfoxides. II. The Preparation of Some Optically Active β -Disulfoxides
Kunieda N, et al.
Bulletin of the Chemical Society of Japan, 49(1), 256-259 (1976)
A highly stereoselective synthesis of d-erythrose derivatives by one-carbon homologation of 2, 3-O-isopropylidene-d-glyceraldehyde with (R)-methyl p-tolyl sulfoxide.
Arroyo-Gomez Y, et al.
Tetrahedron Asymmetry, 11(3), 789-796 (2000)
The reaction of nitrones with (R)-(+)-methyl p-tolyl sulfoxide anion; asymmetric synthesis of optically active secondary amines.
Murahashi S-I, et al.
Tetrahedron Letters, 34(16), 2645-2648 (1993)

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