99395-88-7

Basic information

• Product Name: (S)-(+)-4-Phenyl-2-oxazolidinone
• Synonyms: (S)-(+)-4-Phenyl-2-oxazolidinone,99%;(S)-(+)-4-Phenyl-2-o;(S)+4-PHENYL-2-OXAZOLDINONE;2-Oxazolidinone, 4-phenyl-, (S)-;S-POZ;(4S)-(+)-2-Oxo-4-phenyl-1,3-oxazolidine, [(4S)-(+)-2-Oxo-1,3-oxazolidin-4-yl]benzene;EzetiMibe IMpurity ((S)-4-Phenyloxazolidin-2-one);(S) - 4 - phenyl - 2 - pbo alkanes
• CAS NO: 99395-88-7
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 1312995-182-4
• Product Categories: chiral;Chiral Reagent;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Peptide;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives;Oxazolidinone;Chiral Compounds
• Mol File: 99395-88-7.mol
• Article Data: 68

Chemical Properties

• Melting Point: 129-132 °C(lit.)
• Boiling Point: 290.25°C (rough estimate)
• Flash Point: 200 °C
• Appearance: White/Crystalline Powder
• Density: 1.2021 (rough estimate)
• Vapor Pressure: 7.79E-07mmHg at 25°C
• Refractive Index: 72 ° (C=1, AcOEt)
• Storage Temp.: Store at 0-5°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.05±0.40(Predicted)
• BRN: 131918
• CAS DataBase Reference: (S)-(+)-4-Phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-4-Phenyl-2-oxazolidinone(99395-88-7)
• EPA Substance Registry System: (S)-(+)-4-Phenyl-2-oxazolidinone(99395-88-7)

Safety Data

• Hazard Codes: Xi,F+
• Statements: 12-36
• Safety Statements: 24/25-33-26-16-7/9
• WGK Germany: 3
• F: 3-9
• Hazardous Substances Data: 99395-88-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 99395-88-7 differently. You can refer to the following data:
1. S)-4-Phenyl-2-oxazolidinone is an intermediate for the synthesis and development for cholesterol absorption inhibitor AZD4121.
2. Ezetimibe intermediate
3. Versatile chiral auxiliary for asymmetric synthesis which is easily recycled under mild conditions, thus enhancing its commercial potential. For a recent review, see Aldrichimica Acta .

InChI:InChI=1/C9H9NO2/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

• 60729-80-8 (S)-2-((ethoxycarbonyl)amino)-2-phenylacetic acid 
• 20989-17-7 (2S)-2-phenylglycinol 
• 105-58-8 Diethyl carbonate 
• 2935-35-5 (S)-2-phenylglycine 
• 503-38-8 trichloromethyl chloroformate 
• 616-38-6 carbonic acid dimethyl ester 
• 20989-17-7 Phenylglycinol 
• 52724-28-4 bis(tetraethylammonium) carbonate 
• 117049-14-6 tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate 
• 130406-31-4 benzyl (S)-(2-hydroxy-1-phenylethyl)carbamate 
• 110143-62-9 (S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester 
• 259184-49-1 (S)-3-benzoyloxypyrrolidine 
• 124-38-9 carbon dioxide 
• 86217-38-1 4-phenyl-2-oxazolidinone 

Downstream Products

• 146137-31-7 (4S)-4-phenyl-3-<3-(4-methoxyphenyl)-2(E)-propenoyl>-2-oxazolidinone 
• 154499-36-2 (4S)-3-(2-methyl-2-propenoyl)-4-phenyl-2-oxazolidinone 
• 290369-84-5 (S)-3-((E)-3-Naphthalen-2-yl-acryloyl)-4-phenyl-oxazolidin-2-one 
• 192203-76-2 (4S)-3-(2-butynoyl)-4-phenyloxazolidin-2-one 
• 192203-79-5 (S)-4-Phenyl-3-(3-trimethylsilanyl-propynoyl)-oxazolidin-2-one 
• 192203-75-1 (4S)-3-(3-phenyl-2-propyonyl)-4-phenyloxazolidin-2-one 
• 197020-74-9 (+)-(1R)-1-phenyl-2-(phenylthio)ethylamine 
• 197644-33-0 (2S,4'S)-4-methylthio-2-(2'-oxo-4'-phenyloxazolidin-3'-yl)butanoic acid 
• 224578-09-0 (S)-3-{(E)-3-[3-Methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-acryloyl}-4-phenyl-oxazolidin-2-one 
• 128947-42-2 (S)-3-acetyl-4-phenyl-1,3-oxazolidin-2-one 
• 189498-31-5 3-((E)-3-cyclopropylpropenoyl)-4-(S)-phenyl-2-oxazolidinone 
• 243121-07-5 (S)-3-[(E)-4,4,4-trifluorobut-2-enoyl]-4-phenyloxazolidin-2-one 
• 294176-63-9 (S)-3-(3-Methyl-but-2-enoyl)-4-phenyl-oxazolidin-2-one 
• 316807-16-6 (7S,8S)-7-Nitro-8-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-nonanoic acid methyl ester 

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.

Preparation method of oxazolidinone compound

The preparation method comprises the following steps 1): dissolving aromatic amino acid in methanol, dissolving the aromatic amino acid in methanol, heating up to 50 - 60 °C heat preservation 1 - 2h, 2) reducing: adding a catalytic amount of lithium salt in ethanol water as a solvent. 3) Ring-closing: toluene is used as a solvent, a reduction product and diethyl carbonate are added to 100 °C, a sodium methoxide solution is added dropwise, and the product is obtained after completion of the dropwise addition and after-treatment and purification after completion of the normal pressure distillation to the temperature of 100 °C heat preservation. The lithium salt is introduced to participate in the reaction, sodium borohydride is selected as a solvent, sodium borohydride is completely dissolved, and the lithium salt can be free from the compound to improve the reaction activity, so that the use amount of sodium borohydride is reduced to 2 equivalent, and the production cost is remarkably reduced.

Chiral separation materials based on derivatives of 6-amino-6-deoxyamylose

In order to develop new type of chiral separation materials, in this study, 6-amino-6-deoxyamylose was used as chiral starting material with which 10 derivatives were synthesized. The amino group in 6-amino-6-deoxyamylose was selectively acylated and then the hydroxyl groups were carbamoylated yielding amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s, which were employed as chiral selectors (CSs) for chiral stationary phases of high-performance liquid chromatography. The resulted 6-amido-6-deoxyamyloses and amylose 6-amido-6-deoxy-2,3-bis(phenylcarbamate)s were characterized by IR, 1H NMR, and elemental analysis. Enantioseparation evaluations indicated that most of the CSs demonstrated a moderate chiral recognition capability. The 6-nonphenyl (6-nonPh) CS of amylose 6-cyclohexylformamido-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) showed the highest enantioselectivity towards the tested chiral analytes; the phenyl-heterogeneous (Ph-hetero) CS of amylose 6-(4-methylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) baseline separated the most chiral analytes; the phenyl-homogeneous (Ph-homo) CS of amylose 6-(3,5-dimethylbenzamido)-6-deoxy-2,3-bis(3,5-dimethylphenylcarbamate) also exhibited a good enantioseparation capability among the developed CSs. Regarding Ph-hetero CSs, the enantioselectivity depended on the combination of the substituent at 6-position and that at 2- and 3-positions; as for Ph-homo CSs, the enantioselectivity was related to the substituent at 2-, 3-, and 6-positions; with respect to 6-nonPh CSs, the retention factor of most analytes on the corresponding CSPs was lower than that on Ph-hetero and Ph-homo CSPs in the same mobile phases, indicating π–π interactions did occur during enantioseparation. Although the substituent at 6-position could not provide π–π interactions, the 6-nonPh CSs demonstrated an equivalent or even higher enantioselectivity compared with the Ph-homo and Ph-hetero CSs.