Ethyl 3-phenylglycidate

Base Information

• Chemical Name: Ethyl 3-phenylglycidate
• CAS No.: 121-39-1
• Molecular Formula: C11H12 O3
• Molecular Weight: 192.214
• Hs Code.: 29189990
• European Community (EC) Number: 204-467-3
• NSC Number: 8899
• UNII: 2VVS520ZWM
• DSSTox Substance ID: DTXSID8025886
• Nikkaji Number: J122.448D
• Wikidata: Q27255668
• Metabolomics Workbench ID: 44995
• ChEMBL ID: CHEMBL1369819
• Mol file: 121-39-1.mol

Synonyms:3-EPG;ethyl 3-phenylglycidate

Chemical Property of Ethyl 3-phenylglycidate

Chemical Property:

• Appearance/Colour: pale yellow liquid
• Vapor Pressure: 0.00184mmHg at 25°C
• Melting Point: 17-18 °C
• Refractive Index: n20/D 1.518(lit.)
• Boiling Point: 96 °C0.5 mm Hg(lit.)
• Flash Point: 113 ºC
• PSA: 38.83000
• Density: 1.102
• LogP: 1.68960
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Solubility.: Insoluble in water
• Water Solubility.: 748.4mg/L at 24℃
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 209

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl3-Phenyloxirane-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: CCOC(=O)C1C(O1)C2=CC=CC=C2
• General Description: ETHYL 3-PHENYLGLYCIDATE is a glycidate ester that can be resolved into its enantiomerically pure form, specifically the (2S,3R)-configuration, using crude Mung bean epoxide hydrolase immobilized in a gelatin matrix. This method achieves high enantiomeric excess (ee >99%) and moderate yields (45%), demonstrating its utility as a sustainable approach for synthesizing chiral intermediates relevant to pharmaceutical applications. The process is optimized for enzyme stability and activity by adjusting gelatin concentration and water content.

Technology Process of Ethyl 3-phenylglycidate

There total 63 articles about Ethyl 3-phenylglycidate 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: 100.0%

ethyl 3-phenyl-2-propenoate (103-36-6) → ethyl 3-phenylglycidate (121-39-1)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 20 ℃; for 24h;

DOI:10.15227/orgsyn.074.0091

Reference yield: 92.0%

ethyl cinnamate (4192-77-2) → ethyl 3-phenylglycidate (121-39-1)

Guidance literature:

With oxone; iodobenzene; trifluoroacetic acid; In chloroform; at 20 ℃; for 1h; Sonication;

DOI:10.1055/s-0039-1690621

Reference yield: 92.0%

benzaldehyde (100-52-7) + chloroacetic acid ethyl ester (105-39-5) → ethyl 3-phenylglycidate (121-39-1)

Guidance literature:

With sodium ethanolate; In ethanol;

upstream raw materials:

ethanol

erythro-2,3-dibromo-3-phenylpropanoic acid

sodium acetate

benzaldehyde

Downstream raw materials:

3-dimethylamino-2-hydroxy-3-phenyl-propionic acid dimethylamide

3-(2-amino-phenylsulfanyl)-2-hydroxy-3-phenyl-propionic acid ethyl ester

ethyl cinnamate

2-oxo-5-phenyl-tetrahydro-furan-3,4-dicarboxylic acid diethyl ester

Refernces

Gelozymes in organic synthesis. Part IV: Resolution of glycidate esters with crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix

10.1016/j.tetasy.2008.01.036

The research focuses on the use of crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in a gelatin matrix for the stereoselective resolution of glycidate esters, specifically ethyl trans-(±)-3-phenyl glycidate (1a) and methyl trans-(±)-3-(4-methoxyphenyl) glycidate (1b). The experiments involved the immobilization of the enzyme in a gelatin gel, which was then used to selectively open the epoxide ring of the glycidate esters, yielding (2S,3R)-glycidate esters with high enantiomeric excess (ee >99%) and good yields (45% for 1a and near quantitative for 1b). The reactions were carried out in diisopropyl ether, and the products were analyzed using chiral HPLC to determine their enantiomeric purity and configuration. The study also explored the effects of gelatin concentration and water content on enzyme stability and activity, optimizing these conditions for the best enzyme performance. The research demonstrated a sustainable and efficient method for the preparation of enantiomerically pure glycidate esters, which are important drug intermediates.