171877-37-5

Basic information

• Product Name: (R)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE
• Synonyms: (R)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE;(R)-4-PHENYLOXAZOLIDINE-2-THIONE;(4R)-4-Phenyl-1,3-oxazolidine-2-thione;(4R)-4-Phenyl-2-thioxo-1,3-oxazolidine;(R)-4-Phenyloxazolidine-2-thione,99%e.e.
• CAS NO: 171877-37-5
• Molecular Formula: C₉H₉NOS
• Molecular Weight: 179.24
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 171877-37-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 272.009 °C at 760 mmHg
• Flash Point: 118.307 °C
• Appearance: /
• Density: 1.275 g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (R)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE(171877-37-5)
• EPA Substance Registry System: (R)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE(171877-37-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 171877-37-5(Hazardous Substances Data)

Usage

Uses

Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries

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-/m0/s1

Upstream product

• 75-15-0 carbon disulfide 
• 56613-80-0 D-2-phenylglycinol 
• 140-89-6 potassium ethyl xanthogenate 
• 183876-19-9 (rac)-4-phenyl-1,3-oxazolidine-2-thione 
• 1468-39-9 Isovaleric anhydride 
• 936741-34-3 (2R,3S)-3-hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxooxazolidin-3-yl]propan-1-one 
• 67-56-1 methanol 

Downstream Products

• 545443-64-9 (R)-2-(4'-bromobut-2'-enylthio)-4-phenyl-Δ²-1,3-oxazoline 
• 936741-31-0 2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxooxazolidin-3-yl]ethanone 
• 1422637-24-8 (4S)-isopropyl-3-[(3R)-((4R)-phenyl-2-thioxo-oxazolidin-3-yl)butyryl]oxazolidin-2-one 
• 1429327-65-0 (4S)-isopropyl-3-[(3S)-((4R)-phenyl-2-thioxo-oxazolidin-3-yl)butyryl]oxazolidin-2-one 
• 110199-18-3 (4R)-4-phenyl-1,3-thiazolidine-2-thione 
• 1328839-29-7 C₁₂H₁₃NO₂S 
• 1328839-27-5 C₁₂H₁₃NO₂S 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 1179812-54-4 C₂₃H₃₀N₂O₄S 
• 1179812-42-0 C₂₃H₃₀N₂O₄S 
• 545443-67-2 (R)-3-(4'-bromobut-2'-en-1'-yl)-4-phenylthiazolidin-2-one 
• 750647-57-5 (R)-N-[(3S)-3-phenyl-3-mercaptobutanoyl]-4-phenyloxazolidin-2-one 
• 896434-07-4 3-Methyl-butyric acid (1R,2R)-2-((R)-4-phenyl-2-thioxo-oxazolidine-3-carbonyl)-1-((S)-1-triethylsilanyloxy-ethyl)-hexyl ester 
• 896434-06-3 (R)-2-((1R,2S)-1-Hydroxy-2-triethylsilanyloxy-propyl)-1-((R)-4-phenyl-2-thioxo-oxazolidin-3-yl)-hexan-1-one 

Relevant articles and documents

Crystal structures and vibrational spectra of racemic and chiral 4-phenyl-1,3-oxazolidine-2-thione

The crystal structures of (rac)- and (R)-4-phenyl-1,3-oxazolidine-2-thione (4-POT) have been determined by X-ray diffraction. The structure of (rac)-4-POT is monoclinic P21/n with a = 11.9096(9) A, b = 5.9523(6) A, c = 12.3563(8) A, β = 91.054(

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).

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines

The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.