(R)-4-Phenyloxazolidine-2-thione

Base Information

• Chemical Name: (R)-4-Phenyloxazolidine-2-thione
• CAS No.: 171877-37-5
• Molecular Formula: C9H9NOS
• Molecular Weight: 179.243
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10445660
• Nikkaji Number: J688.770H
• Wikidata: Q82264166
• Mol file: 171877-37-5.mol

Synonyms:(R)-4-Phenyloxazolidine-2-thione;171877-37-5;(R)-4-Phenyl-1,3-oxazolidine-2-thione;(4R)-4-phenyl-1,3-oxazolidine-2-thione;2-Oxazolidinethione,4-phenyl-, (4R)-;(4R)-4-Phenyl-2-thioxo-1,3-oxazolidine;DTXSID10445660;4alpha-Phenyloxazolidine-2-thione;AMY36758;WGA87737;MFCD06658220;CS-W017256;AS-78090;(R)-4-Phenyloxazolidine-2-thione, >=98.0%;E78118;A881906;J-010775

Chemical Property of (R)-4-Phenyloxazolidine-2-thione

Chemical Property:

• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.647
• Boiling Point: 272.009 °C at 760 mmHg
• Flash Point: 118.307 °C
• PSA: 53.35000
• Density: 1.275 g/cm³
• LogP: 1.96120
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 179.04048508
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

98%min ^*data from raw suppliers

(R)-4-Phenyloxazolidine-2-thione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: C1C(NC(=S)O1)C2=CC=CC=C2
• Isomeric SMILES: C1[C@H](NC(=S)O1)C2=CC=CC=C2
• Uses: Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries

Technology Process of (R)-4-Phenyloxazolidine-2-thione

There total 8 articles about (R)-4-Phenyloxazolidine-2-thione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

D-2-phenylglycinol (56613-80-0) + potassium ethyl xanthogenate (140-89-6) → (R)-4-phenyl-1,3-oxazolidine-2-thione (171877-37-5)

Guidance literature:

In ethanol; at 100 ℃; for 1h; Solvent; Temperature; Time;

DOI:10.1080/00397911.2017.1368083

Reference yield: 82.0%

D-2-phenylglycinol (56613-80-0) + potassium ethyl xanthogenate (140-89-6) → (4R)-4-phenyl-1,3-thiazolidine-2-thione (110199-18-3) + (R)-4-phenyl-1,3-oxazolidine-2-thione (171877-37-5)

Guidance literature:

In ethanol; at 100 ℃; for 24h; Solvent; Inert atmosphere; Sealed tube;

DOI:10.1055/s-0037-1612124

Reference yield: 73.0%

D-2-phenylglycinol (56613-80-0) + 2,2‐difluoro‐2‐(triphenylphosphonio)acetate → (R)-4-phenyl-1,3-oxazolidine-2-thione (171877-37-5)

Guidance literature:

With sulfur; In 1,2-dimethoxyethane; at 80 ℃; for 0.0833333h; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.201710186

upstream raw materials:

carbon disulfide

D-2-phenylglycinol

(2R,3S)-3-hydroxy-3-(4-methoxyphenyl)-2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxooxazolidin-3-yl]propan-1-one

methanol

Downstream raw materials:

(R)-2-(4'-bromobut-2'-enylthio)-4-phenyl-Δ²-1,3-oxazoline

2-phenylselanyl-1-[(4R)-4-phenyl-2-thioxooxazolidin-3-yl]ethanone

(4R)-4-phenyl-1,3-thiazolidine-2-thione

C₁₂H₁₃NO₂S

Refernces

• 1、 Lu, Zheng,Yang, Yong-Qing,Xiong, Weixiang. "Preparation of 1,3-Thiazolidine-2-thiones by Using Potassium Ethylxanthate as a Carbon Disulfide Surrogate". supporting information. p. 713 - 716. Retrieved 2019/03/26.
• 2、 Lu, Zheng,Yang, Yong-Qing,Li, Jiu-Hui,Wei, Jun-Nan,Wang, Yi-Zhu. "Convenient approach to chiral 4-monosubstituted 1,3-oxazolidine-2-thiones". supporting information. p. 2215 - 2219. Retrieved 2017/10/31.