(S)-4-methylbenzenesulfinamide

Base Information

• Chemical Name: (S)-4-methylbenzenesulfinamide
• CAS No.: 188447-91-8
• Molecular Formula: C7H9NOS
• Molecular Weight: 155.221
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID40455696
• Wikidata: Q72488201
• Mol file: 188447-91-8.mol

Synonyms:(S)-4-methylbenzenesulfinamide;188447-91-8;(S)-(+)-p-Toluenesulfinamide;(S)-4-Methylbezenesulfinamide;(S)-4-TOLUENESULFINAMIDE;(S)-p-toluenesulfinamide;Benzenesulfinamide, 4-methyl-, (S)-;MFCD06858375;(S)-4-Methyl-benzenesulfinic acid amide;Benzenesulfinamide, 4-methyl-, [S(S)]-;S-4-methylbenzenesulfinamide;(s)-(+)-p-tolylsulfinamide;AMY936;SCHEMBL1645074;DTXSID40455696;YNJDSRPIGAUCEE-JTQLQIEISA-N;(S)-4-methylbenzene-1-sulfinamide;AKOS015897534;(S)-(+)-p-Toluenesulfinamide, 98%;CS-W019426;SB76106;TS-02069;T2069

Chemical Property of (S)-4-methylbenzenesulfinamide

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 118-121 °C(lit.)
• Refractive Index: 1.65
• Boiling Point: 322.362 °C at 760 mmHg
• PKA: 9.52±0.40(Predicted)
• Flash Point: 148.76 °C
• PSA: 62.30000
• Density: 1.29 g/cm³
• LogP: 2.54230
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 155.04048508
• Heavy Atom Count: 10
• Complexity: 130

Purity/Quality:

98% ^*data from raw suppliers

(S)-(+)-p-Toluenesulfinamide >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)N
• Isomeric SMILES: CC1=CC=C(C=C1)[S@](=O)N
• Uses: (S)-(+)-p-Toluenesulfinamide 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.

Technology Process of (S)-4-methylbenzenesulfinamide

There total 29 articles about (S)-4-methylbenzenesulfinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(SS)-menthyl p-toluenesulfinate → (S)-p-toluenesulfinimide (188447-91-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c0ob00078g

Reference yield: 86.0%

(S)-(+)-1-methyl 4-methylbenzenesulfinate (59203-01-9) → (S)-p-toluenesulfinimide (188447-91-8)

Guidance literature:

(S)-(+)-1-methyl 4-methylbenzenesulfinate; With lithium hexamethyldisilazane; In toluene; at -78 ℃; for 3h; Inert atmosphere;

With ammonium chloride; In water; at 20 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Cooling with dry ice;

DOI:10.1016/j.tetasy.2011.01.028

Reference yield: 86.0%

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) → (S)-p-toluenesulfinimide (188447-91-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

DOI:10.1021/jo9820622

upstream raw materials:

(-)-menthyl p-toluenesulfinate

lithium hexamethyldisilazane

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

(-)-tert-butyl (S)-4-methylbenzenesulfinate

Downstream raw materials:

(S)-4-mehyl-N-(5-phenylpentylidene)-benzenesulfinamide

(S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide

(S_S,2R)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide

(S)-(+)-N-[3,3-(ethylenedioxy)-3-phenylpropylidene]-p-toluenesulfinamide

Refernces

• 1、 Miaskiewicz, Solène,Reed, John H.,Donets, Pavel A.,Oliveira, Caio C.,Cramer, Nicolai. "Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions". supporting information. p. 4039 - 4042. Retrieved 2018/03/13.
• 2、 -. "Method for synthesizing chiral optical pure para-toluene sulfenamide". . . Retrieved 2018/09/21.