(S)-(+)-p-Toluenesulfinamide - CAS 188447-91-8

(S)-(+)-p-Toluenesulfinamide (CAS# 188447-91-8) is used as a reagent to synthesize (-)-Pinidinol, a piperidine alkaloid usually extracted from pine and spruce trees(S)-(+)-p-Toluenesulfinamide is also used as a reagent in the synthesis of Nelfinavir, a selective inhibitor of human immunodeficiency virus (HIV) protease that is used to treat patients with HIV.

Catalog Number

188447-91-8

CAS

188447-91-8

IUPAC Name

(S)-4-methylbenzenesulfinamide

Synonyms

(S)-4-methylbenzenesulfinamide; (S)-4-methylbenzenesulfinamide

Molecular Weight

155.22

Molecular Formula

C7H9NOS

Product Information

Canonical SMILES

CC1=CC=C(C=C1)S(=O)N

InChI

InChI=1S/C7H9NOS/c1-6-2-4-7(5-3-6)10(8)9/h2-5H,8H2,1H3/t10-/m0/s1

InChI Key

YNJDSRPIGAUCEE-JTQLQIEISA-N

Purity

98 %

MDL

MFCD06858375

Physical State

Solid

Appearance

Powder or crystals

Boiling Point

322.4 ℃ / 760 mmHg

Melting Point

120 ℃

Density

1.28 g/cm³

Optical Activity

+85°( c = 1 in chloroform)

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P261 - P280 - P305+P351+P338

Hazard Statements

H302 - H315 - H319 - H332 - H335

Reference Reading

1. Synthesis of enantiopure sulfinimines (thiooxime s-oxides) catalyzed by yb(otf)(3) from p-toluenesulfinamide and aldehydes in mild reaction conditions.

W H Chan, A W M Lee, Zhi-Yong Jiang. J Org Chem. 2005 Feb 4; 70(3): 1081-3. DOI: 10.1021/jo048597e. PMID: 15675877.

Enantiomerically pure sulfinimines as important building blocks in the asymmetric synthesis of amine derivatives are prepared in good to excellent yields from chiral p-toluenesulfinamide with aromatic, heteroaromatic, and aliphatic aldehydes. The unprecedented feature of the reported procedure is that the formation of the sulfinimines was achieved by the catalytic action of Yb(OTf)(3) in THF at room temperature. The reaction conditions were also applicable to Ellman's sulfinimines.

The molarity calculator equation

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