3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid

Base Information

• Chemical Name: 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid
• CAS No.: 23598-72-3
• Molecular Formula: C11H8ClNO3
• Molecular Weight: 237.642
• Hs Code.: 2934990002
• European Community (EC) Number: 245-770-0
• NSC Number: 81238
• UNII: B7ISJ0S9T5
• DSSTox Substance ID: DTXSID4066913
• Nikkaji Number: J24.400G
• Wikidata: Q72457176
• Mol file: 23598-72-3.mol

Synonyms:23598-72-3;3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid;5-methyl-3-(2'-chlorophenyl)-4-isoxazolecarboxylic acid;3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid;4-Isoxazolecarboxylic acid, 3-(2-chlorophenyl)-5-methyl-;3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid;4-Isoxazolecarboxylic acid, 3-(o-chlorophenyl)-5-methyl-;EINECS 245-770-0;NSC 81238;3-(2-Chlorophenyl)-5-methyl-isoxazole-4-carboxylic acid;cmic acid;NSC81238;MFCD00020813;3-(2-Chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid;Cambridge id 5549841;4-Carboxy-3-(2-chlorophenyl)-5-methylisoxazole;B7ISJ0S9T5;SCHEMBL459354;DTXSID4066913;NSC-81238;STK325639;AKOS000120474;TS-03330;CS-0085276;FT-0613546;EN300-18171;VU0023400-2;AB00088580-01;A816791;CLOXACILLIN SODIUM IMPURITY D [EP IMPURITY];W-110574;3-o-chlorophenyl-5-methylisoxazole-4-carboxylic acid;Z57254347;3-(2-chlorophenyl)-5-methylisoxazol-4-carboxylic acid;3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid;3-(o-chlorophenyl)-5-methylisoxazole-4-carboxylic acid;F3351-0438;3-(2-Chlorophenyl) -5-methyl-Isoxazole-4-carboxylic acid

Chemical Property of 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid

Chemical Property:

• Appearance/Colour: Cream solid
• Vapor Pressure: 2.83E-06mmHg at 25°C
• Melting Point: 186 °C
• Refractive Index: 1.59
• Boiling Point: 374.5 °C at 760 mmHg
• PKA: 2.07±0.25(Predicted)
• Flash Point: 180.3 °C
• PSA: 63.33000
• Density: 1.385 g/cm³
• LogP: 3.00160
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 237.0192708
• Heavy Atom Count: 16
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-37/38-36
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)O
• Uses: 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic Acid (Cloxacillin EP Impurity D) is used in the preparation of isoxazolecarboxamides as a class of TGR5 agonists. Also used in the preparation of β-lactamase inhibitors.

Technology Process of 3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid

There total 7 articles about 3-(2-Chlorophenyl)-5-methylisoxazole-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 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylate (83817-50-9) → 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid (23598-72-3)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/j.bmcl.2004.11.075

Reference yield: 90.0%

→ 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid (23598-72-3)

Guidance literature:

With methanol; sodium hydroxide; at 30 ℃; for 7h;

Reference yield:

2-chloro-benzaldehyde (89-98-5) + acetoacetic acid methyl ester (105-45-3) → 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid (23598-72-3)

Guidance literature:

2-chloro-benzaldehyde; With hydroxylamine sulfate; In methanol; at 20 - 40 ℃; for 1h;

With chlorine; sodium carbonate; triethylamine; In methanol; at 0 - 20 ℃; for 24h; pH=~ 9.5; Inert atmosphere;

acetoacetic acid methyl ester; With sodium carbonate; In methanol; pH=~ 7 - 7.5;

upstream raw materials:

methyl 3-(2'-chlorophenyl)-5-methylisoxazole-4-carboxylate

ethyl 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylate

2-chloro-N-hydroxybenzimidoyl chloride

2-chloro benzaldehyde oxime

Downstream raw materials:

3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride

3-(2-chloro-5-nitro-phenyl)-5-methyl-isoxazole-4-carboxylic acid

3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid cyclohexylamide

3-(2-chloro-phenyl)-5-propyl-isoxazole-4-carboxylic acid

Refernces

• 1、 Wang, Wei,Wang, Lie-Ping,Mao, Min-Zhen,Zhang, Xiao-Guang,Zheng, Xiao-Rui,Huang, Xiao-Ying,Xue, Chao,Ning, Bin-Ke. "Synthesis and biological activity of ethyl 2-(5-methyl-3-arylisoxazole-4-carboxamido)-4-alkylthiazole-5-carboxylate". supporting information. p. 164 - 167. Retrieved 2017/11/20.
• 2、 Ramana, P. Venkata,Reddy, A. Ram. "Synthesis of 1,2,3-triazole substituted isoxazoles via copper (I) catalyzed cycloaddition". experimental part. p. 621 - 627. Retrieved 2012/09/07.