185137-29-5

Basic information

• Product Name: (S)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE
• Synonyms: (S)-4-PHENYLTHIAZOLIDINE-2-THIONE;(S)-(+)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE;(S)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE;(S)-4-Phenylthiazolidine-2-thione;(S)-4-Phenylthiazolidine-2-thione,99%e.e.
• CAS NO: 185137-29-5
• Molecular Formula: C₉H₉NS₂
• Molecular Weight: 195.3
• Mol File: 185137-29-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 127.0 to 131.0 °C
• Boiling Point: 322.2 °C at 760 mmHg
• Flash Point: 148.7 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 0.000284mmHg at 25°C
• Refractive Index: 1.7
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (S)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE(185137-29-5)
• EPA Substance Registry System: (S)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE(185137-29-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 185137-29-5(Hazardous Substances Data)

Usage

General Description

(S)-4-Phenyl-1,3-thiazolidine-2-thione is a chemical compound with the molecular formula C8H9NS2. It is a thiazolidine derivative, containing a thione functional group. The compound is a white to off-white powder and is an important intermediate in the synthesis of pharmaceuticals and agrochemicals. It has shown antibacterial and antifungal activities and is being studied for its potential as an anti-inflammatory and antidiabetic agent. (S)-4-Phenyl-1,3-thiazolidine-2-thione is also used in the production of rubber additives, dyes, and other specialty chemicals. It is important to handle this compound with caution as it may be harmful if ingested or inhaled, and can cause skin and eye irritation.

InChI:InChI=1/C9H9NS2/c11-9-10-8(6-12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)/t8-/m1/s1

Upstream product

• 1908-90-3 (rac)-4-phenyl-1,3-thiazolidine-2-thione 
• 1468-39-9 Isovaleric anhydride 
• 62779-70-8 (1S)-1-phenylethylene-1,2-diamine 
• 75-15-0 carbon disulfide 
• 150884-50-7 benzaldehyde N-boc imine 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 34375-80-9 4-phenyl-4-oxazoline-2-one 
• 1435664-93-9 C₁₂H₁₃NOS₂ 
• 1435664-91-7 C₁₃H₁₅NOS₂ 
• 137102-30-8 (S)-N₁-tert-butoxycarbonyl-1-phenyl-1,2-ethanediamine 
• 100-52-7 benzaldehyde 
• 20989-17-7 (2S)-2-phenylglycinol 
• 25260-42-8 (S)-(+)-2-phenylaziridine 

Downstream Products

• 1039757-81-7 (S)-4-phenyl-N-propanoyl-1,3-thiazolidine-2-thione 
• 1448350-64-8 N-(2-aminophenyl)-4-({[(4S)-4-phenyl-4,5-dihydro-1,3-thiazol-2-yl]sulfanyl}methyl)benzamide 
• 1383790-23-5 C₂₂H₂₂N₂OS₄ 
• 1383790-21-3 (4S)-3-((2E)-butenoyl)-4-phenylthiazolidine-2-thione 
• 1332631-10-3 N-(2-hydroxyethyl)-4-phenylthiazolidine-2-thione 
• 1332631-06-7 C₁₁H₁₃NOS₂ 
• 401613-72-7 (4S,4'S)-(1-benzoyl-4-phenyl-1,4-dihydropyridin-3-yl)-(4'-phenyl-2'-thioxo-1',3'-thiazolidine-3'-yl)methanone 
• 230309-12-3 (4S,4'S)-4-benzyl-3-(4'-phenyl-2'-thioxo-1',3'-thiazolidine-3'-carbonyl)-4H-pyridine-1-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).

Kinetic resolution of N-acyl-thiolactams via catalytic enantioselective deacylation

Methanolysis of N-acyl-thiazolidin-2-thiones and -oxazolidin-2-thiones in the presence of acyl transfer catalyst benzotetramisole (BTM) proceeds in a highly enantioselective fashion thus enabling kinetic resolution of these substrates.