Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

343609

Sigma-Aldrich

(R)-(+)-Methyl p-tolyl sulfoxide

99%

Synonym(s):

(+)-(R)-Methyl 4-tolyl sulfoxide, (+)-Methyl p-tolyl sulfoxide, (R)-4-Methylphenyl methyl sulfoxide, 1-Methyl-4-[(R)-methylsulfinyl]benzene

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CH3C6H4S(O)CH3
CAS Number:
1519-39-7
Molecular Weight:
154.23
Beilstein:
2040677
MDL number:
MFCD00151502
UNSPSC Code:
12191600
PubChem Substance ID:
24861180
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D +145°, c = 2 in acetone

optical purity

ee: 99% (HPLC)

mp

73-75 °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-/m1/s1

InChI key

FEVALTJSQBFLEU-SNVBAGLBSA-N

Looking for similar products? Visit Product Comparison Guide

General description

(R)-(+)-Methyl p-tolyl sulfoxide may be used to prepare (R)-(+)-methyl 3,5-dimethoxy-6-[8-oxo-9-(p-tolylsulfinyl) nonyl] benzoate, an intermediate for (R)-lasiodiplodin synthesis. Its anions undergo addition reaction with nitrones to form optically active a-substituted N-hydroxylamines. (R)-(+)-Methyl p-tolyl sulfoxide also reacts with O-mesitylsulfonylhydroxylamine (MSH) to form (-)-(R)-S-methyl-S-p-tolylsulfoximine.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000227560
0000235100
BGBC5326V
MKBH4047V
MKBB3168

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Chemistry of sulfoxides and related compounds. XLIX. Synthesis of optically active sulfoximines from optically active sulfoxides.
Johnson CR, et al.
The Journal of Organic Chemistry, 39(16), 2458-2459 (1974)
Asymmetric synthesis of orsellinic acid type macrolides: The example of lasiodiplodin.
Solladie G, et al.
Tetrahedron Asymmetry, 1(3), 187-198 (1990)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service