5-(4-Chlorophenyl)isoxazole-3-carboxylic acid

Base Information

• Chemical Name: 5-(4-Chlorophenyl)isoxazole-3-carboxylic acid
• CAS No.: 33282-22-3
• Molecular Formula: C10H6 Cl N O3
• Molecular Weight: 223.616
• Hs Code.: 2934999090
• European Community (EC) Number: 624-413-6
• DSSTox Substance ID: DTXSID00360696
• Wikidata: Q82142563
• Mol file: 33282-22-3.mol

Synonyms:5-(4-Chlorophenyl)isoxazole-3-carboxylic acid;33282-22-3;5-(4-chlorophenyl)-1,2-oxazole-3-carboxylic acid;5-(4-Chloro-phenyl)-isoxazole-3-carboxylic acid;MFCD06010034;5-(4-chlorophenyl)-3-isoxazolecarboxylic acid;SCHEMBL892967;DTXSID00360696;BBL010080;STK344188;AKOS000263513;(2R)-2-Amino-4-phosphonobutyric acid;AB22988;FS-5279;BB 0253152;CS-0085275;FT-0679621;EN300-26243;D94718;A875338;AS-871/43476098;SR-01000370531;J-019126;SR-01000370531-1;5-(4-Chlorophenyl)isoxazole-3-carboxylic acid, 97%

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

Chemical Property:

• Vapor Pressure: 3.71E-09mmHg at 25°C
• Melting Point: 200.0 °C (dec.)(lit.)
• Boiling Point: 457.3°Cat760mmHg
• PKA: 3.24±0.10(Predicted)
• Flash Point: 230.4°C
• PSA: 63.33000
• Density: g/cm³
• LogP: 2.69320
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 223.0036207
• Heavy Atom Count: 15
• Complexity: 241

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-(4-Chlorophenyl)isoxazole-3-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=NO2)C(=O)O)Cl

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

There total 6 articles about 5-(4-Chlorophenyl)isoxazole-3-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-(4-chlorophenyl)isoxazole-3-carboxylate (81282-12-4) → 5-(3-chlorophenyl)isoxazole-1-carboxylic acid (33282-22-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2.5h;

DOI:10.1016/j.molstruc.2019.127144

Reference yield: 70.0%

4-(4-chlorophenyl)but-3-en-2-one oxime (86425-09-4) → 5-(3-chlorophenyl)isoxazole-1-carboxylic acid (33282-22-3)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In chloroform; for 4h; Reflux; Green chemistry;

DOI:10.1080/00397911.2013.854916

Reference yield:

para-chloroacetophenone (99-91-2) → 5-(3-chlorophenyl)isoxazole-1-carboxylic acid (33282-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium / ethanol / 4 h / 0 - 20 °C

2: hydroxylamine hydrochloride / ethanol / 2.5 h / Reflux

3: lithium hydroxide / tetrahydrofuran; water / 2.5 h / 20 °C

With hydroxylamine hydrochloride; sodium; lithium hydroxide; In tetrahydrofuran; ethanol; water;

DOI:10.1016/j.molstruc.2019.127144

upstream raw materials:

ethyl 5-(4-chlorophenyl)isoxazole-3-carboxylate

4-(4-chlorophenyl)but-3-en-2-one oxime

4-(4-chlorophenyl)-3-buten-2-one

ethyl 4-(4-chlorophenyl)-2-hydroxy-4-oxobut-2-enoate

Downstream raw materials:

C₁₀H₅Cl₂NO₂

Refernces

• 1、 Habib, Farhat,Alam, Shadab,Hussain, Afzal,Aneja, Babita,Irfan, Mohammad,Alajmi, Mohamed F.,Hasan, Phool,Khan, Parvez,Rehman, Md Tabish,Noman, Omar Mohammed,Azam, Amir,Abid, Mohammad. "Biofilm inhibition and DNA binding studies of isoxazole-triazole conjugates in the development of effective anti-bacterial agents". . . Retrieved 2019/10/14.
• 2、 Saeedi, Mina,Mohtadi-Haghighi, Dorrin,Mirfazli, Seyedeh Sara,Mahdavi, Mohammad,Hariri, Roshanak,Lotfian, Hania,Edraki, Najmeh,Iraji, Aida,Firuzi, Omidreza,Akbarzadeh, Tahmineh. "Design and Synthesis of Selective Acetylcholinesterase Inhibitors: Arylisoxazole-Phenylpiperazine Derivatives". . . Retrieved 2019/02/09.