Methyl isoxazole-5-carboxylate

Base Information

• Chemical Name: Methyl isoxazole-5-carboxylate
• CAS No.: 15055-81-9
• Molecular Formula: C5H5NO3
• Molecular Weight: 127.10
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20371683
• Nikkaji Number: J1.403.630J
• Wikidata: Q82159105
• Mol file: 15055-81-9.mol

Synonyms:Methyl isoxazole-5-carboxylate;15055-81-9;methyl 1,2-oxazole-5-carboxylate;5-Isoxazolecarboxylic acid, methyl ester;MFCD01570794;Isoxazole-5-carboxylic acid methyl ester;5-Isoxazolecarboxylic Acid Methyl Ester;Methylisoxazole-5-carboxylate;SCHEMBL4066379;DTXSID20371683;ILPCPKZAAQXHKL-UHFFFAOYSA-N;AMY38613;GEO-02776;STK510319;5-Isoxazolecarboxylicacid,methyl ester;AKOS003672830;5-isoxazolecarboxylic acid,methyl ester;AS-64776;SY078826;FT-0737857;EN300-232203;F53681;W-200125;9b,11b-Epoxy-17,21-dihydroxypregna-1,4-diene-3,20-dione

Chemical Property of Methyl isoxazole-5-carboxylate

Chemical Property:

• Vapor Pressure: 0.271mmHg at 25°C
• Melting Point: 48-51 °C
• Refractive Index: 1.462
• Boiling Point: 203.9 °C at 760 mmHg
• PKA: -3.88±0.50(Predicted)
• Flash Point: 77.1 °C
• PSA: 52.33000
• Density: 1.23 g/cm³
• LogP: 0.46120
• XLogP3: 0.6
• 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:

99% ^*data from raw suppliers

5-IsoxazolecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=NO1
• Uses: 5-Isoxazolecarboxylic Acid Methyl Ester is used as a reagent in the synthesis of pyridine derivatives as integrase inhibitors and antiviral agents. 5-Isoxazolecarboxylic Acid Methyl Ester is also a useful synthetic intermediate in the preparation of pyrazolopyrimidine derivatives useful in the prevention and treatment of cancer.

Technology Process of Methyl isoxazole-5-carboxylate

There total 6 articles about Methyl isoxazole-5-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: 81.0%

ISOXAZOLE (288-14-2) + carbon dioxide (124-38-9,18923-20-1) + methyl iodide (74-88-4) → methyl 1,2-oxazole-5-carboxylate (15055-81-9)

Guidance literature:

carbon dioxide; With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.25h; under 1125.11 Torr;

ISOXAZOLE; In tetrahydrofuran; at 20 ℃; for 12h; under 1125.11 Torr;

methyl iodide; In tetrahydrofuran; regioselective reaction;

DOI:10.1021/ja103429q

Reference yield: 72.0%

methanol (67-56-1) + isoxazole-5-carboxylic acid (21169-71-1) → methyl 1,2-oxazole-5-carboxylate (15055-81-9)

Guidance literature:

With sulfuric acid; for 20h; Heating / reflux;

Reference yield: 42.7%

isoxazole-5-carboxylic acid (21169-71-1) + methyl iodide (74-88-4) → methyl 1,2-oxazole-5-carboxylate (15055-81-9)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 25 ℃; for 19h;

upstream raw materials:

diazomethane

isoxazole-5-carboxylic acid

N-hydroxyformimidoyl iodide

propynoic acid methyl ester

Downstream raw materials:

5-isoxazolecarboxaldehyde

2-cyanomethylene-3-oxo-1,2,3,4-tetrahydroquinoxaline

Refernces

• 1、 -. "INTEGRASE INHIBITORS 3". Page/Page column 61. . Retrieved 2008/06/13.