Methyl 5-oxazolecarboxylate

Base Information

• Chemical Name: Methyl 5-oxazolecarboxylate
• CAS No.: 121432-12-0
• Molecular Formula: C5H5NO3
• Molecular Weight: 127.1
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50369194
• Wikidata: Q72494034
• Mol file: 121432-12-0.mol

Synonyms:Methyl 5-oxazolecarboxylate;121432-12-0;methyl oxazole-5-carboxylate;methyl 1,3-oxazole-5-carboxylate;Methyl5-oxazolecarboxylate;SCHEMBL2928096;DTXSID50369194;JGJDORZNOSWWDS-UHFFFAOYSA-N;AMY10991;MFCD00144774;AKOS006271594;Oxazole-5-carboxylic acid methyl ester;DS-14035;CS-0044071;FT-0660244;W-205117

Chemical Property of Methyl 5-oxazolecarboxylate

Chemical Property:

• Vapor Pressure: 0.751mmHg at 25°C
• Melting Point: 44-46 °C
• Refractive Index: 1.462
• Boiling Point: 184 °C at 760 mmHg
• PKA: -1.19±0.10(Predicted)
• Flash Point: 65.1 °C
• PSA: 52.33000
• Density: 1.229 g/cm³
• LogP: 0.46120
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 127.026943022
• Heavy Atom Count: 9
• Complexity: 115

Purity/Quality:

98% ^*data from raw suppliers

MethylOxazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CN=CO1

Technology Process of Methyl 5-oxazolecarboxylate

There total 2 articles about Methyl 5-oxazolecarboxylate 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: 60.0%

glyoxylic acid ethyl ester (924-44-7) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) → methyl oxazole-5-carboxylate (121432-12-0)

Guidance literature:

With potassium carbonate; In methanol; toluene; for 7h; Heating / reflux;

Reference yield:

methanol (67-56-1) + glyoxylic acid ethyl ester (924-44-7) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) → methyl oxazole-5-carboxylate (121432-12-0) + oxazol-5-yl-carboxylic acid ethyl ester (118994-89-1)

Guidance literature:

methanol; glyoxylic acid ethyl ester; With caesium carbonate; In tetrahydrofuran; at 50 ℃; for 0.5h;

[(p-methylphenyl)sulfonylmethyl]isonitrile; In tetrahydrofuran; acetic acid; at 60 ℃; for 1h;

DOI:10.1021/acs.oprd.8b00006

Reference yield: 62.0%

methyl oxazole-5-carboxylate (121432-12-0) → methyl 2-chloro-1,3-oxazole-5-carboxylate (934236-41-6)

Guidance literature:

methyl oxazole-5-carboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -40 ℃; for 1h;

With hexachloroethane; In tetrahydrofuran; at -40 - 20 ℃; for 16h;

upstream raw materials:

glyoxylic acid ethyl ester

[(p-methylphenyl)sulfonylmethyl]isonitrile

methanol

Downstream raw materials:

1,3-oxazol-5-ylmethanol

methyl 2-chloro-1,3-oxazole-5-carboxylate

methyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

Refernces

• 1、 Edney, Dean,Hulcoop, David G.,Leahy, John H.,Vernon, Lois E.,Wipperman, Mark D.,Bream, Robert N.,Webb, Michael R.. "Development of Flexible and Scalable Routes to Two Phosphatidinylinositol-3-kinase Delta Inhibitors via a Common Intermediate Approach". . p. 368 - 376. Retrieved 2018/03/22.