Tepoxalin

Base Information

• Chemical Name: Tepoxalin
• CAS No.: 103475-41-8
• Molecular Formula: C20H20ClN3O3
• Molecular Weight: 385.85
• European Community (EC) Number: 638-877-2
• UNII: TZ4OX61974
• DSSTox Substance ID: DTXSID1057610
• Nikkaji Number: J357.517I
• Wikipedia: Tepoxalin
• Wikidata: Q7701370
• NCI Thesaurus Code: C76817
• Pharos Ligand ID: 8QL8QAFVZ45F
• Metabolomics Workbench ID: 144388
• ChEMBL ID: CHEMBL316040
• Mol file: 103475-41-8.mol

Synonyms:5-(4-chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide;ORF 20485;ORF-20485;tepoxalin

Chemical Property of Tepoxalin

Chemical Property:

• Vapor Pressure: 5.72E-14mmHg at 25°C
• Melting Point: 124-126°
• Refractive Index: 1.61
• Boiling Point: 572.991 °C at 760 mmHg
• Flash Point: 300.334 °C
• PSA: 67.59000
• Density: 1.27 g/cm³
• LogP: 3.98150
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 385.1193192
• Heavy Atom Count: 27
• Complexity: 479

Purity/Quality:

99% ^*data from raw suppliers

Tepoxalin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(=O)CCC1=NN(C(=C1)C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)OC)O
• Uses: Tepoxalin is non-steroidal anti-inflammatory drug (NSAID) with potent anti-inflammatory and analgesic properties approved for veterinary use. It has inhibitory effect on cyclooxygenase and 5-lipxygenase activity a s well as inhibiting the production of cytokines in peripheral cells outside the CNS. Non-steroidal anti-inflammatory drug (NSAID) with potent anti-inflammatory and analgesic properties approved for veterinary use. It has inhibitory effect on cyclooxygenase and 5-lipxygenase activity as well as inhibiting the production of cytokines in peripheral cells outside the CNS.

Technology Process of Tepoxalin

There total 10 articles about Tepoxalin 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: 87.9%

→ tepoxalin (103475-41-8)

Guidance literature:

Reference yield: 65.0%

oxalyl dichloride (79-37-8) + triethylamine (Et3 N) + N-methylhydroxyamine hydrochloride (4229-44-1) + water (7732-18-5) + 3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]propionic acid (114150-42-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → tepoxalin (103475-41-8)

Guidance literature:

In tetrahydrofuran;

Reference yield: 10.0%

4-methoxyphenylhydrazine hydrochloride (19501-58-7) + 6-(4-chlorophenyl)-4,6-dioxo-N-hydroxy-N-methylhexanamide (142791-64-8) → tepoxalin (103475-41-8) + 3-<3-(4-chlorophenyl)-1-(4-methoxyphenyl)-5-pyrazolyl>-N-hydroxy-N-methylpropanamide (149065-93-0)

Guidance literature:

With sodium carbonate; In ethanol; for 3h; Heating;

DOI:10.1021/jo00050a059

upstream raw materials:

N-methylhydroxyamine hydrochloride

3-[5-(4-Chloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-propionyl chloride

4-methoxyphenylhydrazine hydrochloride

6-(4-chlorophenyl)-4,6-dioxo-N-hydroxy-N-methylhexanamide

Downstream raw materials:

3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl] N-Chloroacetyloxy-N-methylpropanamide

Refernces

• 1、 Murray, William V.,Hadden, Susan K.. "A Facile Synthesis of Tepoxalin, 5-(4-Chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide". . p. 6662 - 6663. Retrieved 2007/10/02.
• 2、 Murray,Wachter,Barton,Forero-Kelly. "The regioselective synthesis of tepoxalin, 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-me thylpropanamide and related 1,5-diarylpyrazole anti-inflammatory agents". . p. 18 - 20. Retrieved 2007/10/02.