Ethyl oxirane-2-carboxylate

Base Information

• Chemical Name: Ethyl oxirane-2-carboxylate
• CAS No.: 4660-80-4
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 2918990090
• European Community (EC) Number: 225-105-0
• DSSTox Substance ID: DTXSID401317010
• Nikkaji Number: J297.875J
• Mol file: 4660-80-4.mol

Synonyms:ethyl glycidate;glycidic acid ethyl ester

Chemical Property of Ethyl oxirane-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.043mmHg at 25°C
• Refractive Index: n20/D 1.4200(lit.)
• Boiling Point: 123.1 °C at 760 mmHg
• Flash Point: 38.3 °C
• PSA: 38.83000
• Density: 1.18 g/cm³
• LogP: -0.05170
• Storage Temp.: 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 99.8

Purity/Quality:

97% ^*data from raw suppliers

Ethyl2,3-epoxypropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/38-43
• Safety Statements: 26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1CO1
• General Description: Ethyl 2,3-epoxypropanoate, also known as ethyl glycidate, is a chemical compound characterized by an oxirane (epoxide) ring attached to an ethyl ester group. It is commonly used as a flavoring agent or intermediate in organic synthesis due to its reactive epoxide functionality. ETHYL 2,3-EPOXYPROPANOATE is structurally related to glycidic acid and its derivatives, which are known for their utility in pharmaceutical and fine chemical applications. Its reactivity makes it valuable for ring-opening reactions and as a precursor for more complex molecules. Safety and handling precautions are necessary due to its potential irritant properties and reactivity.

Technology Process of Ethyl oxirane-2-carboxylate

There total 14 articles about Ethyl oxirane-2-carboxylate 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: 95.0%

dimethyl 8'-7',8'-dimethyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate (73245-18-8) → dimethyl 4,5-dimethylphthalate (17649-59-1) + ethyl glycidate (4660-80-4)

Guidance literature:

In ethanol; chloroform; at 12 - 20 ℃; for 1h;

DOI:10.1021/jo01299a030

Reference yield: 90.0%

dimethyl 1',8'-dimethyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate (73245-21-3) → dimethyl 3,5-dimethylphthalate (50919-64-7) + ethyl glycidate (4660-80-4)

Guidance literature:

In ethanol; chloroform; at 12 - 20 ℃; for 1h;

DOI:10.1021/jo01299a030

Reference yield: 88.0%

dimethyl 1'-methyl-8'-tert-butyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate (73245-23-5) → ethyl glycidate (4660-80-4) + dimethyl 5-(tert-butyl)-3-methylphthalate (73195-01-4)

Guidance literature:

In ethanol; chloroform; at 12 - 20 ℃; for 1h;

DOI:10.1021/jo01299a030

upstream raw materials:

ethyl acrylate

dimethyl 8'-7',8'-dimethyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate

dimethyl 1',8'-dimethyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate

dimethyl 1'-methyl-8'-tert-butyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate

Downstream raw materials:

3-(2-Amino-phenylamino)-2-hydroxy-propionic acid ethyl ester

ethyl 3-hydroxypropanoate

ethyl (2RS)-2-hydroxy-3-N-(R-tetrahydropapaverinyl)propionate

N,N-(2RS,13RS)-2,13-di(ethoxycarbonyl)-3,12-dioxa-4,11-dioxotetradecylene-1,14-diyl-bis(R-tetrahydropapaverine)

Refernces

10.1021/ja01649a029

The research aims to explore the synthesis of dimethyl-(α-hydroxy-β-propiothetin) hydrochloride (IIb) and related compounds as part of a broader study on sulfonium compounds as potential lipotropic agents. The researchers used various routes to synthesize IIb, including reactions of dimethyl sulfide with epoxides and acid-catalyzed reactions with lactones. Key chemicals involved include dimethyl sulfide, hydrogen chloride, ethylene oxide, potassium glycidate, ethyl glycidate, and methyl glycidate. The study found that while sulfonium compounds could be obtained from these reactions, yields were generally low (10 to 20%), likely due to competing reactions such as epoxide ring cleavage by hydrogen chloride. The researchers also synthesized related compounds like sulfocholine hydrochloride (IIa), (2-hydroxy-2-carbethoxy)-ethyldimethylsulfonium chloride (IIc), and (1,1-dimethyl-2-hydroxy-2-carbomethoxy)-ethyldimethylsulfonium chloride (IId) through similar methods. The study concludes that while the synthesis of these compounds is feasible, improving yields remains a challenge, and further research is needed to optimize the reaction conditions and explore alternative synthetic routes.