188447-91-8

Basic information

• Product Name: (S)-4-Methylbezenesulfinamide
• Synonyms: (S)-4-Methylbezenesulfinamide (S)-(+)-p-Toluenesulfinamide;(S)-(+)-p-Toluenesulfinamide;(S)-4-Methylbezenesulfimide;(S)-4-Methylbezenesulfinamide,99%e.e.;(S)-4-METHYL-BENZENESULFINAMIDE;(S)-4-Methylbezenesulfinamide;(S)-4-TOLUENESULFINAMIDE;(S)-4-TOLUENESULPHINAMIDE
• CAS NO: 188447-91-8
• Molecular Formula: C₇H₉NOS
• Molecular Weight: 155.22
• Product Categories: Chiral Compound;Chiral Building Blocks;Organic Building Blocks;Sulfonamides/Sulfinamides
• Mol File: 188447-91-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 118-121 °C(lit.)
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: white to light yellow crystal powder
• Density: 1.29 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 9.52±0.40(Predicted)
• CAS DataBase Reference: (S)-4-Methylbezenesulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Methylbezenesulfinamide(188447-91-8)
• EPA Substance Registry System: (S)-4-Methylbezenesulfinamide(188447-91-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 188447-91-8(Hazardous Substances Data)

Usage

Description

(S)-4-Methylbezenesulfinamide, also known as (S)-(+)-p-Toluenesulfinamide, is a white to light yellow crystalline powder with unique chemical properties. It is a chiral reagent that plays a significant role in the synthesis of various organic compounds and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
(S)-4-Methylbezenesulfinamide is used as a reagent for the synthesis of (-)-Pinidinol, a piperidine alkaloid commonly extracted from pine and spruce trees. This alkaloid has potential applications in the development of pharmaceuticals due to its unique chemical structure and properties.
(S)-4-Methylbezenesulfinamide is also used as a reagent in the synthesis of Nelfinavir, a selective inhibitor of human immunodeficiency virus (HIV) protease. Nelfinavir is an essential medication used to treat patients with HIV, helping to manage the progression of the disease and improve the quality of life for those affected.

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

Upstream product

• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 90252-89-4 p-tolylzinc(II) chloride 
• 59203-01-9 (S)-(+)-1-methyl 4-methylbenzenesulfinate 
• 1307296-48-5 (R,S)-N-Benzyl-N-(1-phenylethyl)-p-toluenesulfinamide 
• 153277-56-6 C₁₃H₂₅NOSSi₂ 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 243671-40-1 N-dihydrocinnamoyl-p-toluenesulfinamide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 6873-55-8 p-tolylsulfinyl amide 
• 934631-21-7 rac-N-3-(3-pyridine)propionyl-p-toluene-sulfinamide 
• 934631-22-8 (S)-N-3-(3-pyridine)propionyl-p-toluene-sulfinamide 
• 847980-58-9 (S)-N-dihydrocinnamoyl-p-toluenesulfinamide 
• 847980-37-4 N-methoxyacetyl-p-toluenesulfinamide 
• 59153-43-4 (-)-tert-butyl (S)-4-methylbenzenesulfinate 

Downstream Products

• 188447-82-7 (S)-(+)-N-(crotonylidene)-p-toluenesulfinamide 
• 174464-94-9 (S)-(+)-(2,2-dimethylpropylidene)-p-toluenesulfinamide 
• 951397-10-7 ethyl 2-(S)-p-tolylsulfinimido-4-p-nitrophenyl-(E)-3-butenoate 
• 160751-25-7 (S)-(-)-N-<(p-methylthio)benzylidene>-p-toluenesulfinamide 
• 503819-65-6 (S)-(+)-N-(p-cyanobenzylidene)-p-toluenesulfinamide 
• 188447-84-9 (S)-N-(butylidene)-4-methylbenzenesulfinamide 
• 193979-96-3 (S)-4-methyl-benzenesulfinic acid propylideneamide 
• 213909-32-1 (S,E)-4-methyl-N-(4-chlorobenzylidene)benzenesulfinamide 
• 188447-78-1 (S)-(+)-N-(p-fluorobenzylidene)-p-toluenesulfinamide 
• 299183-66-7 (S)-(-)-N-(piperonylmethylidene)-p-toluenesulfinamide 
• 186249-72-9 (+)-(S)-(E)-N-(3-E-phenylpropenylidene)-p-toluenesulfinamide 

Relevant articles and documents

Chiral-at-Ruthenium Catalysts with Mixed Normal and Abnormal N-Heterocyclic Carbene Ligands

We recently reported a new class of chiral ruthenium catalysts in which two achiral bidentate N-(2-pyridyl)-substituted N-heterocyclic carbene ligands in addition to two labile acetonitriles are coordinated to a central ruthenium and generate a stereogenic metal center which is responsible for the overall chirality (Zheng et al. J. Am. Chem. Soc. 2017, 139, 4322). Here we now report our discovery of related chiral-at-ruthenium catalysts in which normal and abnormal N-heterocyclic carbene (NHC) ligands are present at the same time. The synthesis of racemic complexes, their resolution into individual enantiomers by a chiral auxiliary approach, and a catalytic application are reported. The mixed normal/abnormal NHC complexes display significantly increased turnover numbers and turnover frequencies for a nitrene-mediated enantioselective C(sp3)-H amination.

Preparation method of chiral optical pure p-toluenesulfinamide

The invention discloses a preparation method of a chiral optical pure p-toluenesulfinamide. The method includes: subjecting sodium p-tolylsulfinate and an acyl chlorination reagent to acyl chlorination to obtain p-toluene sulfinyl chloride, then reacting

Preparation method of chiral optical pure p-toluene sulfamide

The invention discloses a preparation method of chiral optical pure p-toluene sulfamide. The preparation method comprises the following steps: performing acylating chlorination by using sodium p-tolylsulfinate and an acylating chlorination reagent to obta