S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine, 98%, Thermo Scientific Chemicals
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S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine, 98%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine, 98%, Thermo Scientific Chemicals

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Catalog number L00577.06
also known as L00577-06
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Chemical Identifiers
CAS22236-45-9
IUPAC Namedimethyl[(4-methylbenzenesulfonyl)imino]-λ⁶-sulfanone
Molecular FormulaC9H13NO3S2
InChI KeyIRNAWARRPQUZDU-UHFFFAOYSA-N
SMILESCC1=CC=C(C=C1)S(=O)(=O)N=S(C)(C)=O
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SpecificationsSpecification SheetSpecification Sheet
Assay (HPLC)≥97.5%
FormCrystals or powder or crystalline powder
Appearance (Color)White
Melting Point166-172°C
S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine, is used as methylene-transfer agent. The anion adds to carbonyl compounds to give epoxides which can react with a further mole of reagent with ring expansion to give 2,2-disubstituted oxetanes. It is also used as a pharmaceutical intermediate.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine, is used as methylene-transfer agent. The anion adds to carbonyl compounds to give epoxides which can react with a further mole of reagent with ring expansion to give 2,2-disubstituted oxetanes. It is also used as a pharmaceutical intermediate.

Solubility
Soluble in EtOH, THF, DMSO.

Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Keep away from oxidizing agents.
RUO – Research Use Only

General References:

  1. CR Johnson.; RA Kirchhoff.; RJ Reischer. Chemistry of sulfoxides and related compounds. XLII. Nucleophilic alkylidene transfer reagents. Anions of N-(p-tolylsulfonyl) sulfoximines. J. Am. Chem. Soc. 197395 (13), 4287-4291.
  2. SL Huang.; D Swern. Oxidation of N-acyl-, N-sulfonyl-, and N-arylsulfilimines to sulfoximines by m-chloroperoxybenzoate anion. The Journal of Organic Chemistry. 197944 (14), 2510-2513.
  3. Methylene-transfer agent. For reviews, see: Acc. Chem. Res., 6, 341 (1973); Chem. Soc. Rev., 4, 189 (1975). The anion adds to carbonyl compounds to give epoxides which can react with a further mole of reagent with ring expansion to give 2,2-disubstituted oxetanes: J. Am. Chem. Soc., 101, 6135 (1979); 105, 252 (1983):