Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate

Base Information

• Chemical Name: Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate
• CAS No.: 2065-28-3
• Molecular Formula: C12H11 N O3
• Molecular Weight: 217.224
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20352492
• Nikkaji Number: J136.565G
• Wikidata: Q82129665
• ChEMBL ID: CHEMBL1723122
• Mol file: 2065-28-3.mol

Synonyms:2065-28-3;methyl 5-methyl-3-phenyl-4-isoxazolecarboxylate;methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate;methyl 5-methyl-3-phenylisoxazole-4-carboxylate;CDS1_000675;5-Methyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester;Maybridge1_002963;MLS000709597;DivK1c_001715;SCHEMBL4683450;CHEMBL1723122;HMS549O15;DTXSID20352492;VJCQAWFSNYNJLG-UHFFFAOYSA-N;4-Isoxazolecarboxylic acid, 5-methyl-3-phenyl-, methyl ester;HMS2706D12;BBL007612;MFCD00119105;STK365545;AKOS000544608;SMR000288064;AM20030314;CS-0279483;FT-0679993;A18432;11B-004;J-522495;Z16184592

Chemical Property of Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 2.13E-05mmHg at 25°C
• Melting Point: 79-81°C
• Boiling Point: 361°Cat760mmHg
• Flash Point: 172.1°C
• PSA: 52.33000
• Density: 1.174g/cm³
• LogP: 2.43660
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 251

Purity/Quality:

98%min ^*data from raw suppliers

Methyl5-methyl-3-phenyl-4-isoxazolecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)OC

Technology Process of Methyl 5-methyl-3-phenyl-1,2-oxazole-4-carboxylate

There total 14 articles about Methyl 5-methyl-3-phenyl-1,2-oxazole-4-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: 85.0%

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 5-methyl-3-phenylisoxazol-4-carboxylic acid (1136-45-4) → methyl 5-methyl-3-phenylisoxazole-4-carboxylate (2065-28-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In methanol; for 24h; Ambient temperature;

DOI:10.1021/jo00207a052

Reference yield: 82.0%

methyl chloroformate (79-22-1) + 4-bromo-5-methyl-3-phenylisoxazole (31295-65-5) → methyl 5-methyl-3-phenylisoxazole-4-carboxylate (2065-28-3)

Guidance literature:

4-bromo-5-methyl-3-phenylisoxazole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.75h;

DOI:10.1021/ol502246t

Reference yield: 65.0%

benzonitrile oxide (873-67-6) + α-chloro methyl crotonate (60753-84-6) → methyl 5-methyl-3-phenylisoxazole-4-carboxylate (2065-28-3)

Guidance literature:

With triethylamine; In benzene; at 70 ℃; for 2h; regioselective reaction; Microwave irradiation;

DOI:10.1002/jhet.5570450521

upstream raw materials:

methanol

5-methyl-3-phenylisoxazole-4-carbonyl chloride

methyl buta-2,3-dienoate

benzohydroximoyl chloride

Downstream raw materials:

4-amino-4-phenyl-3-(methoxycarbonyl)-3-buten-2-one

5-methyl-3-phenyl-4-isoxazolylmethanol

5-bromomethyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester

5-dibromomethyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester

Refernces

• 1、 Xu, Hui,Fan, Guang-Peng,Liu, Zi,Wang, Guan-Wu. "Catalyst- and solvent-free mechanochemical synthesis of isoxazoles from N-hydroxybenzimidoyl chlorides and enamino carbonyl compounds". . p. 6607 - 6611. Retrieved 2018/10/05.
• 2、 Dong, Kui-Yong,Qin, Hai-Tao,Bao, Xing-Xing,Liu, Feng,Zhu, Chen. "Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin". . p. 5266 - 5268. Retrieved 2015/01/09.