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481858

Sigma-Aldrich

Methyl p-tolyl sulfoxide

97%

Synonym(s):

(±)-Methyl p-toluene sulfoxide, (±)-p-Tolyl methyl sulfoxide, 1-Methanesulfinyl-4-methylbenzene, 1-Methyl-4-(methylsulfinyl)benzene, 4-(Methylsulfinyl)toluene, 4-Methylphenyl methyl sulfoxide, 4-Toluene methyl sulfoxide, Methyl 4-methylphenyl sulfoxide, p-Methylphenyl methyl sulfoxide, p-Tolyl methyl sulfoxide

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About This Item

Linear Formula:
CH3C6H4S(O)CH3
CAS Number:
934-72-5
Molecular Weight:
154.23
MDL number:
MFCD00075175
UNSPSC Code:
12352100
PubChem Substance ID:
24871787
NACRES:
NA.22

Assay

97%

bp

113-114 °C/2 mmHg (lit.)

mp

44-46 °C (lit.)

functional group

sulfoxide

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

InChI key

FEVALTJSQBFLEU-UHFFFAOYSA-N

Related Categories

General description

Methyl p-tolyl sulfoxide (MTSO), an alkyl-substituted p-tolyl sulfoxide, is a Lewis base. It behaves as an activator of silicon tetrachloride that is employed in aza-Diels-Alder reaction.

Application

Methyl p-tolyl sulfoxide may be used as a catalyst in the preparation of homoallylic alcohols by the allylation of aldehydes with allyltrichlorosilane. It may be used as a ligand in the synthesis of molybdenum chlorocomplexes.

Caution

Low melting solid

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000359406
0000340979
0000359406
0000253220
0000180666

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DEET PESTANAL®, analytical standard

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36542

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Methyl phenyl sulfone ≥98.0% (GC)

Sigma-Aldrich

68742

Methyl phenyl sulfone

A New Approach to Di-and Tetrasubstituted 2,3-Dihydropyridin-4(1H)-ones through Aza-Diels-Alder Reaction Promoted by Silicon Tetrachloride.
Peduto A, et al.
Synthesis, 4, 0643-0649 (2009)
Luisa A Denkel et al.
PloS one, 6(11), e26974-e26974 (2011-11-11)
Production of reactive oxygen species represents a fundamental innate defense against microbes in a diversity of host organisms. Oxidative stress, amongst others, converts peptidyl and free methionine to a mixture of methionine-S- (Met-S-SO) and methionine-R-sulfoxides (Met-R-SO). To cope with such
Asymmetric allylation of aldehydes with allyltrichlorosilane promoted by chiral sulfoxides.
Massa A, et al.
Tetrahedron Letters, 44(38), 7179-7181 (2003)
Addition compounds of MoO2Cl2 with chiral sulfoxides. First molecular structures of dioxomolybdenum complexes bearing chiral non-racemic sulfoxide as ligand.
Pedrosa MR, et al.
Inorgorganica Chimica Acta, 363(13), 3158-3164 (2010)
Yuuka Masuyama et al.
Drug metabolism and pharmacokinetics, 35(3), 274-280 (2020-04-20)
Flavin containing monooxygenases (FMOs) represent one of the predominant types of phase I drug metabolizing enzymes (DMEs), and thus play an important role in the metabolism of xeno- and endobiotics for the generation of their corresponding oxides. These oxides often

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