110199-18-3

Basic information

• Product Name: (R)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE
• Synonyms: (R)-(-)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE;(R)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE;(R)-4-PHENYLTHIAZOLIDINE-2-THIONE;(4R)-4-phenyl-1,3-thiazolidine-2-thione;(R)-4-Phenylthiazolidine-2-thione
• CAS NO: 110199-18-3
• Molecular Formula: C₉H₉NS₂
• Molecular Weight: 195.3
• Mol File: 110199-18-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 128.0 to 130.0 °C
• Boiling Point: 322.2 °C at 760 mmHg
• Flash Point: 148.662 °C
• Appearance: /
• Density: 1.317 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.7
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 12.28±0.40(Predicted)
• CAS DataBase Reference: (R)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE(110199-18-3)
• EPA Substance Registry System: (R)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE(110199-18-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 110199-18-3(Hazardous Substances Data)

Usage

Uses

Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries

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-/m0/s1

Upstream product

• 140-89-6 potassium ethyl xanthogenate 
• 171877-37-5 (R)-4-phenyl-1,3-oxazolidine-2-thione 
• 56613-80-0 D-2-phenylglycinol 
• 1908-90-3 (rac)-4-phenyl-1,3-thiazolidine-2-thione 
• 1468-39-9 Isovaleric anhydride 
• 75-15-0 carbon disulfide 
• 936741-47-8 (2R,3S,4E)-3-hydroxy-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]oct-4-en-1-one 
• 67-56-1 methanol 
• 936741-45-6 (2R,3S)-3-hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]propan-1-one 

Downstream Products

• 936741-32-1 2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]ethanone 
• 1039757-81-7 (S)-4-phenyl-N-propanoyl-1,3-thiazolidine-2-thione 
• 1217320-19-8 (R)-N-propionyl-4-phenylthiazolidine-2-thione 
• 1334180-43-6 (4R)-N-[(3S)-3-allyloxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 1334180-32-3 (4R)-N-[(3R)-3-allyloxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 1334180-53-8 (4R)-N-[(3S)-3-methoxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 1334180-52-7 (4R)-N-[(3R)-3-methoxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 936741-47-8 (2R,3S,4E)-3-hydroxy-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]oct-4-en-1-one 
• 936741-45-6 (2R,3S)-3-hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxothiazolidin-3-yl]propan-1-one 
• 827603-88-3 2-((S)-Diphenyl-methanesulfinyl)-1-((R)-4-phenyl-2-thioxo-thiazolidin-3-yl)-ethanone 
• 827603-84-9 2-((R)-Diphenyl-methanesulfinyl)-1-((R)-4-phenyl-2-thioxo-thiazolidin-3-yl)-ethanone 
• 153496-49-2 (4R)-3-methyl-4-phenylthiazolidin-2-one 

Relevant articles and documents

Preparation of 1,3-Thiazolidine-2-thiones by Using Potassium Ethylxanthate as a Carbon Disulfide Surrogate

A simple procedure is presented for preparing 1,3-thiazolidine-2-thiones by using potassium ethylxanthate and the corresponding β -amino alcohols as the starting materials in the presence of ethanol.

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).

Diastereoselective aldolization with N-phenylselanylacetyl derivatives

The asymmetric introduction of the phenylselanyl moiety using chiral N-phenyselanylacetyloxazolidin-2-thiones and -thiazolidin-2-thiones is reported. The diastereoselectivity is complete in favor of the syn isomer and the aldols so obtained are valuable intermediates for the synthesis of more functionalized molecules such as amino alcohols, after chemoselective activation of the selenium and substitution by nucleophilic nitrogen. Georg Thieme Verlag Stuttgart.