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339997

(S)-(−)-Methyl p-tolyl sulfoxide

Name: (<I>S</I>)-(−)-Methyl <I>p</I>-tolyl sulfoxide
Brand: ALDRICH

99%

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About This Item

Linear Formula:

CH₃C₆H₄S(O)CH₃

CAS Number:

5056-07-5

Molecular Weight:

154.23

UNSPSC Code:

12191600

NACRES:

NA.22

PubChem Substance ID:

24860755

MDL number:

MFCD00151503

Beilstein/REAXYS Number:

2324696

Assay:

99%

Form:

solid

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Properties

Quality Level

100

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

Description

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000210511

0000217284

0000206223

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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)

Global Trade Item Number

SKU	GTIN
339997-1G	04061826062937