Methyl oxirane-2-carboxylate

Base Information

• Chemical Name: Methyl oxirane-2-carboxylate
• CAS No.: 4538-50-5
• Molecular Formula: C4H6O3
• Molecular Weight: 102.09
• Hs Code.: 2918990090
• European Community (EC) Number: 610-247-1
• DSSTox Substance ID: DTXSID50963378
• Nikkaji Number: J455.920G
• Mol file: 4538-50-5.mol

Synonyms:methyl oxirane-2-carboxylate;4538-50-5;Glycidic acid methyl ester;Methyl glycidate;Oxiranecarboxylic acid, methyl ester;methyl 2,3-epoxypropionate;Methyl-2,3-epoxypropanoate;MFCD17676228;Cucurbitaceae;bitter cucumber;Methyl (2S)-2,3-epoxypropanoate;MFCD00274190;MFCD00274191;methyl epoxypropionate;Methyl(2R)-glycidate;Methyl(2R)-oxirane-2-carboxylate;COC(=O)C1CO1;Methyl 2-oxiranecarboxylate #;SCHEMBL839705;DTXSID50963378;AMY42223;BCP18462;AKOS015899973;PB39596;PB47461;Oxirane-2-carboxylic acid, methyl ester;AS-44350;SY029485;SY029486;SY103832;FT-0642904;FT-0645738;FT-0769561;EN300-75814;( inverted exclamation markA)-Methyl glycidate;A826790;Oxirane, 2-carboxylic acid methyl ester_Gurudeeban & Satyavani

Chemical Property of Methyl oxirane-2-carboxylate

Chemical Property:

• Vapor Pressure: 41.7mmHg at 25°C
• Refractive Index: 1.444
• Boiling Point: 97.4 °C at 760 mmHg
• Flash Point: 26.2 °C
• PSA: 38.83000
• Density: 1.246g/cm³
• LogP: -0.44180
• Storage Temp.: -20°C, Inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 102.031694049
• Heavy Atom Count: 7
• Complexity: 88.9

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CO1
• General Description: Glycidic acid methyl ester (also known as racemic methyl glycidate, methyl 2-oxiranecarboxylate, or methyl oxirane-2-carboxylate) is a versatile intermediate used in organic synthesis, such as in the preparation of (±)-eusynstyelamide A, where it reacts with 6-bromoindole and Boc-protected agmatine. Additionally, glycidates, including methyl glycidate, can be efficiently synthesized through the oxidation of acrylates using NaOCl in the presence of ammonium salts under slightly basic conditions, yielding high product efficiency when the appropriate ammonium salts are selected.

Technology Process of Methyl oxirane-2-carboxylate

There total 17 articles about Methyl 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: 97.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl glycidate (4538-50-5)

Guidance literature:

With Mn-trimethyltriazacyclononane; dihydrogen peroxide; sodium L-ascorbate; In water; acetonitrile; at 0 ℃;

DOI:10.1016/S0040-4039(99)01595-6

Reference yield: 82.0%

R-oxiranecarboxylic acid potassium salt (82044-23-3) + dimethyl sulfate (77-78-1) → methyl (2R)-glycidate (4538-50-5,85485-00-3,118712-39-3,111058-32-3)

Guidance literature:

With 18-crown-6 ether; In acetonitrile; for 1h;

Reference yield: 65.0%

potassium de l'acide (S)-(-)-epoxy-2,3 propionique (82079-45-6) + dimethyl sulfate (77-78-1) → methyl (2S)-glycidate (4538-50-5,85485-00-3,111058-32-3,118712-39-3)

Guidance literature:

With 18-crown-6 ether; In acetonitrile;

DOI:10.1016/S0040-4039(00)96028-3

upstream raw materials:

acrylic acid methyl ester

methacrylic acid methyl ester

potassium de l'acide (S)-(-)-epoxy-2,3 propionique

dimethyl sulfate

Downstream raw materials:

methyl (2R)-2,3-dihydroxypropanoate

methyl L-glycerate

methyl (2S)-glycidate

methyl (2R)-glycidate

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.