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

• 20989-17-7 (2S)-2-phenylglycinol 
• 140-89-6 potassium ethyl xanthogenate 
• 75-09-2 dichloromethane 
• 75-15-0 carbon disulfide 
• 25260-42-8 (S)-(+)-2-phenylaziridine 
• 1908-90-3 (rac)-4-phenyl-1,3-thiazolidine-2-thione 
• 1468-39-9 Isovaleric anhydride 
• 100-52-7 benzaldehyde 
• 137102-30-8 (S)-N₁-tert-butoxycarbonyl-1-phenyl-1,2-ethanediamine 
• 62779-70-8 (1S)-1-phenylethylene-1,2-diamine 
• 150884-50-7 benzaldehyde N-boc imine 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 1435664-91-7 C₁₃H₁₅NOS₂ 
• 1435664-93-9 C₁₂H₁₃NOS₂ 

Downstream Products

• 230309-03-2 (4S)-(4-phenyl-2-thioxo-1,3-diazolidin-3-yl)-pyridin-3-yl-methanone 
• 861224-12-6 1-((S)-4-Phenyl-2-thioxo-thiazolidin-3-yl)-icosan-1-one 
• 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 
• 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 
• 1039757-81-7 (S)-4-phenyl-N-propanoyl-1,3-thiazolidine-2-thione 
• 1332631-06-7 C₁₁H₁₃NOS₂ 
• 1332631-10-3 N-(2-hydroxyethyl)-4-phenylthiazolidine-2-thione 
• 1383790-23-5 C₂₂H₂₂N₂OS₄ 
• 1383790-21-3 (4S)-3-((2E)-butenoyl)-4-phenylthiazolidine-2-thione 

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).

Discovery of potent, isoform-selective inhibitors of histone deacetylase containing chiral heterocyclic capping groups and a N-(2-aminophenyl)benzamide binding unit

The synthesis of a novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contain a heterocyclic capping group and a N-(2-aminophenyl)benzamide unit that binds in the active site. In vitro assays for the inhibition of HDAC1, HDAC2, HDAC3-NCoR1, and HDAC8 by the N-(2-aminophenyl)benzamide 24a gave respective IC50 values of 930, 85, 12, and 4100 nM, exhibiting class I selectivity and potent inhibition of HDAC3-NCoR1. Both imidazolinone and thiazoline rings are shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl) benzamides previously reported, an example of each ring system at 1 μM causing an increase in histone H3K9 acetylation in the human cell lines Jurkat and HeLa and an increase in cell death consistent with induction of apoptosis. Inhibition of the growth of MCF-7, A549, DU145, and HCT116 cell lines by 24a was observed, with respective IC50 values of 5.4, 5.8, 6.4, and 2.2 mM.