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

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

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 
• 4039-32-1 lithium hexamethyldisilazane 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 59153-43-4 (-)-tert-butyl (S)-4-methylbenzenesulfinate 
• 847980-37-4 N-methoxyacetyl-p-toluenesulfinamide 
• 847980-58-9 (S)-N-dihydrocinnamoyl-p-toluenesulfinamide 
• 934631-22-8 (S)-N-3-(3-pyridine)propionyl-p-toluene-sulfinamide 
• 934631-21-7 rac-N-3-(3-pyridine)propionyl-p-toluene-sulfinamide 
• 6873-55-8 p-tolylsulfinyl amide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 243671-40-1 N-dihydrocinnamoyl-p-toluenesulfinamide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 153277-56-6 C₁₃H₂₅NOSSi₂ 
• 1307296-48-5 (R,S)-N-Benzyl-N-(1-phenylethyl)-p-toluenesulfinamide 

Downstream Products

• 188447-76-9 (S,E)-4-methyl-N-(4-nitrobenzylidene)benzenesulfinamide 
• 216855-39-9 (S)-N-(p-tolylsulfinylimino)triphenylphosphorane 
• 220732-37-6 (S)-4-mehyl-N-(5-phenylpentylidene)-benzenesulfinamide 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 220732-34-3 (S)-(E)-N-ethylidene-4-methylbenzenesulfinamide 
• 65440-68-8 [S-(E)]-(+)-N-α-methylbenzylidene-p-toluenesulfinamide 
• 220732-31-0 (S)-(+)-N-(m-methoxybenzylidene)-p-toluenesulfinamide 
• 620165-39-1 (S)-(+)-N-(5-benzyloxy-1-pentylidene)-p-toluenesulfinamide 
• 318471-70-4 (S)-(+)-N-(1,2,2-trimethylpropylidene)-p-toluenesulfinamide 
• 310435-47-3 (S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide 
• 310435-49-5 (S_S,2R)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide 
• 318471-67-9 (S)-(+)-N-α-methyl-(4-methylbenzylidene)-p-toluenesulfinamide 
• 65461-41-8 [S-(E/Z)]-(+)-N-α-ethylbenzylidene-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.

Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions

Secondary 1,3,2-diazaphospholenes have a polarized P?H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of α,β-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.

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

Method for synthesizing chiral optical pure para-toluene sulfenamide

The invention discloses a method for synthesizing chiral optical pure para-toluene sulfonamide. The method comprises the following steps: ensuring that para-toluene sulfinic acid sodium salt and an acylating chlorination reagent react with each other, so

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

Monoligated Pd(0)-catalyzed intramolecular ortho- and para-arylation of phenols for the synthesis of aporphine alkaloids. Synthesis of (-)-lirinine

An intramolecular palladium(0)-mediated ortho-arylation of phenols applied to the synthesis of various substituted aporphines is reported. Most significantly, the efficiency of the transformation was enhanced by the use of monoligated Pd(0) complexes. This methodology was extended to para-arylation of phenols and employed in the synthesis of the aporphine alkaloid (-)-lirinine.

Asymmetric synthesis of sulfinamides using (-)-quinine as chiral auxiliary

A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.

Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)- arylsulfinamides

A novel and simple process for the preparation of enantiomerically pure (SS)-benzenesulfinamide (SS)-3a, (SS)-p- toluenesulfinamide (SS)-3b, (SS)-p-chloro- benzenesulfinamide (SS)-3c and (SS)-p- fluorobenzenesulfinamide (SS)-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)- arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,SS)-N-benzyl-N-(1-phenylethyl)- arylsulfinamides (R,SS)-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,SS)-1 were then converted into four enantiopure (RS)-methyl arylsulfinates (RS)-2, and finally into four enantiopure (SS)- arylsulfinamides (SS)-3 in good yields.

Chiral sulfur derivatives in the allylation of acyl hydrazones: C 2-symmetric bis-sulfinamides as enhanced chiral organic promoters.

Monosulfinamides and C2-symmetric bis-sulfinamides are convenient neutral chiral promoters in the allylation of acyl hydrazones, the nature of the spacer and the substituent at the sulfinyl sulfur are key elements for the enantioselectivity of the process.

Synthesis of enantiopure sulfonimidamides and elucidation of their absolute configuration by comparison of measured and calculated CD spectra and X-ray crystal structure determination

Straightforward syntheses of enantiopure N-benzoyl- and N-tert-butyloxycarbonyl-protected sulfonimidamides, which can be used as building blocks in newly designed catalysts, are presented. Key synthetic step is a dynamic resolution of a racemic sulfinic acid sodium salt. All subsequent transformations proceed stereospecifically. The absolute configurations at the sulfur atoms of both sulfonimidamides were determined by comparison of measured and calculated CD spectra. An X-ray crystal structure determination of a sulfonimidoylguanidine derivative confirmed this result.