190970-57-1

Basic information

• Product Name: (S)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE
• Synonyms: (S)-4-PHENYLOXAZOLIDINE-2-THIONE;(S)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE;2-Oxazolidinethione, 4-phenyl-, (4S)-;(S)-4-Phenyloxazolidine-2-thione,99%e.e.
• CAS NO: 190970-57-1
• Molecular Formula: C₉H₉NOS
• Molecular Weight: 179.24
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 190970-57-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 272.009 °C at 760 mmHg
• Flash Point: 118.307 °C
• Appearance: /
• Density: 1.275 g/cm³
• Vapor Pressure: 0.00624mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (S)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE(190970-57-1)
• EPA Substance Registry System: (S)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE(190970-57-1)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 190970-57-1(Hazardous Substances Data)

Usage

General Description

(S)-4-Phenyl-1,3-oxazolidine-2-thione is a chemical compound belonging to the oxazolidine class. It is an enantiomer of the compound 4-Phenyl-1,3-oxazolidine-2-thione and has a thione functional group. (S)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE has been studied for its potential biological activities, including as a potential antiviral and antimicrobial agent. It has also been investigated for its role as a chiral ligand in asymmetric catalysis. The thione group in this compound gives it unique reactivity and potential applications in various chemical and biological processes.

InChI:InChI=1/C9H9NOS/c12-9-10-8(6-11-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,12)/t8-/m1/s1

Upstream product

• 75-15-0 carbon disulfide 
• 20989-17-7 (2S)-2-phenylglycinol 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 67-66-3 chloroform 
• 183876-19-9 (rac)-4-phenyl-1,3-oxazolidine-2-thione 
• 1435666-01-5 C₁₃H₁₅NO₂S 
• 1468-39-9 Isovaleric anhydride 
• 1169704-42-0 3-(2-(2R)-phenylpropanoyl)-4(4S)-phenyloxazolidin-2-thione 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 1169704-43-1 C₁₉H₁₉NO₂S 
• 1169704-45-3 (S)-pentafluorophenyl 2-phenylbutanoate 
• 1169704-46-4 C₁₉H₁₉NO₂S 
• 851913-12-7 pentafluorophenyl (S)-2-(4-isobutylphenyl)propionate 
• 1169704-47-5 C₂₂H₂₅NO₂S 
• 872989-08-7 (+)-pentafluorophenyl 2-(6-methoxy-naphthalen-2-yl)propionate 
• 1169704-49-7 C₂₃H₂₁NO₃S 
• 1169704-48-6 C₁₈H₁₆ClNO₂S 
• 1169704-44-2 C₂₀H₂₁NO₂S 
• 878194-06-0 (R)-pentafluorophenyl 2-phenylpropionate 
• 931405-93-5 pentafluorophenyl (S)-2-phenylpropionate 
• 1169704-42-0 3-(2-(2R)-phenylpropanoyl)-4(4S)-phenyloxazolidin-2-thione 

Relevant articles and documents

Preparation method of (S)-4-phenyl-2-oxazolidinone

The invention discloses a preparation method for synthesizing (S)-4-phenyl-2-oxazolidinone, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: reducing N-Boc-L-phenylglycine with a borane reagent to obtain N-Boc-L-phenylglycinol, and carrying out a ring closing reaction under the action of a catalyst to obtain (S)-4-phenyl-2-oxazolidinone. The product reacts with sulfur powder and ammonium sulfide or ammonium polysulfide to obtain (S)-4-phenyl oxazolidine-2-thioketone. The method avoids the use of cytotoxic reagents or solvents, has the advantages of accessible raw materials, simple operation and the like, conforms to green chemistry, and has potential industrial amplification prospects.

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).

Liquid Chromatographic Resolution of Racemic 2-Oxazolidinones and their Analogs on Seven Pirkle-Type Chiral Stationary Phases

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