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Quality Level
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 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
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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Find documentation for the products that you have recently purchased in the Document Library.
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.
Tetrahedron Asymmetry, 11(3), 789-796 (2000)
β -Disulfoxides. II. The Preparation of Some Optically Active β -Disulfoxides
Bulletin of the Chemical Society of Japan, 49(1), 256-259 (1976)
The reaction of nitrones with (R)-(+)-methyl p-tolyl sulfoxide anion; asymmetric synthesis of optically active secondary amines.
Tetrahedron Letters, 34(16), 2645-2648 (1993)
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