5-Methyl-3-phenylisoxazole-4-carboxylic acid

Base Information

• Chemical Name: 5-Methyl-3-phenylisoxazole-4-carboxylic acid
• CAS No.: 1136-45-4
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• Hs Code.: 2934990002
• European Community (EC) Number: 214-497-9
• NSC Number: 76870
• UNII: ZL8HD4RP5B
• DSSTox Substance ID: DTXSID3061556
• Nikkaji Number: J41.512J
• Wikidata: Q27463383
• Mol file: 1136-45-4.mol

Synonyms:5-methyl-3-phenylisoxazole-4-carboxylic acid

Chemical Property of 5-Methyl-3-phenylisoxazole-4-carboxylic acid

Chemical Property:

• Appearance/Colour: cream to pale brown solid
• Vapor Pressure: 5.74E-06mmHg at 25°C
• Melting Point: 192-194 °C(lit.)
• Refractive Index: 1.578
• Boiling Point: 365 °C at 760 mmHg
• PKA: 2.11±0.32(Predicted)
• Flash Point: 174.5 °C
• PSA: 63.33000
• Density: 1.273g/cm³
• LogP: 2.34820
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

5-Methyl-3-phenyl-4-isoxazolecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22
• Safety Statements: 24/25-36/37-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)O
• Uses: 5-Methyl-3-phenylisoxazole-4-carboxylic acid was used in preparation of intermediates for the synthesis of penicillin. It was used for acylation during solid support synthesis of the isoxazolopyridone derivatives.

Technology Process of 5-Methyl-3-phenylisoxazole-4-carboxylic acid

There total 25 articles about 5-Methyl-3-phenylisoxazole-4-carboxylic acid 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: 100.0%

ethyl 5-methyl-3-phenylisoxazole-4-carboxylate (1143-82-4) → 5-methyl-3-phenylisoxazol-4-carboxylic acid (1136-45-4)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/j.bmcl.2004.11.075

Reference yield: 79.0%

5-methyl-3-phenyl-isoxazole-4-carboxylic acid tert-butyl ester → 5-methyl-3-phenylisoxazol-4-carboxylic acid (1136-45-4)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 4h;

Reference yield: 75.0%

benzonitrile oxide (873-67-6) + 2-Butynoic acid (590-93-2) → 5-methyl-3-phenylisoxazol-4-carboxylic acid (1136-45-4)

Guidance literature:

With 2-nitrophenylboronic acid; In 1,2-dichloro-ethane; at 25 ℃; for 24h; regioselective reaction; Inert atmosphere;

DOI:10.1002/chem.200903484

upstream raw materials:

benzonitrile oxide

2-Butynoic acid

5-methyl-3-phenylisoxazole-4-carboxaldehyde

ethyl 5-methyl-3-phenylisoxazole-4-carboxylate

Downstream raw materials:

5-methyl-3-phenylisoxazole

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

5-methyl-3-(3-nitrophenyl)isoxazole-4-carboxylic acid

5-Methyl-3-phenyl-isoxazole-4-carboxylic acid (4-hydroxy-8-methyl-2-oxo-2H-chromen-3-yl)-amide

Refernces

• 1、 Basavanna, V.,Bhadraiah, U. K.,Chandra,Chandramouli, M.,Doddamani, Shridevi,Kempaiah, C.,Lingegowda, N. S.,Ningaiah, S.. "A New Series of 1,3,4-Oxadiazole Linked Quinolinyl-Pyrazole/Isoxazole Derivatives: Synthesis and Biological Activity Evaluation". . p. 2257 - 2266. Retrieved 2021/12/23.
• 2、 Fu, Ying,Gao, Shuang,Gao, Ying-Chao,Guo, Ke-Liang,Li, Juan-Juan,Wang, Zi-Wei,Ye, Fei,Zhao, Li-Xia. "Design, synthesis, and bioevaluation of substituted phenyl isoxazole analogues as herbicide safeners". . p. 10550 - 10559. Retrieved 2020/11/05.