5-(4-chlorophenyl)-1,3-oxazole-4-carboxylic Acid

Base Information

• Chemical Name: 5-(4-chlorophenyl)-1,3-oxazole-4-carboxylic Acid
• CAS No.: 143659-14-7
• Molecular Formula: C10H6ClNO3
• Molecular Weight: 223.60
• Hs Code.: 2934999090
• European Community (EC) Number: 674-626-3
• DSSTox Substance ID: DTXSID10374042
• Wikidata: Q72457283
• Mol file: 143659-14-7.mol

Synonyms:143659-14-7;5-(4-Chlorophenyl)oxazole-4-carboxylic acid;5-(4-chlorophenyl)-1,3-oxazole-4-carboxylic Acid;5-(4-Chlorophenyl)oxazole-4-carboxylicacid;5-(4-Chloro-phenyl)-oxazole-4-carboxylic acid;SCHEMBL1167383;DTXSID10374042;WGPXKQGURSURNU-UHFFFAOYSA-N;MFCD00105450;AKOS010901133;PS-5717;CS-0212439;FT-0716180;A884905

Chemical Property of 5-(4-chlorophenyl)-1,3-oxazole-4-carboxylic Acid

Chemical Property:

• Boiling Point: 381.5 °C at 760 mmHg
• Flash Point: 184.6 °C
• PSA: 63.33000
• Density: 1.44 g/cm³
• LogP: 2.69320
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• 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%min ^*data from raw suppliers

5-(4-Chlorophenyl)oxazole-4-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=C(N=CO2)C(=O)O)Cl

Technology Process of 5-(4-chlorophenyl)-1,3-oxazole-4-carboxylic Acid

There total 5 articles about 5-(4-chlorophenyl)-1,3-oxazole-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: 87.0%

5-(4-chlorophenyl)oxazole-4-carboxylic acid methyl ester (89204-93-3) → 5-(4-chlorophenyl)oxazole-4-carboxylic acid (143659-14-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2004.03.037

Reference yield:

methyl 3-(4-chlorophenyl)-3-oxopropanoate (22027-53-8) → 5-(4-chlorophenyl)oxazole-4-carboxylic acid (143659-14-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 16 h / 20 °C

2: 55 percent / dirhodium tetraoctanoate / CH₂Cl₂ / Heating

3: 65 percent / triphenylphosphine; iodine; triethylamine / CH₂Cl₂ / 16 h

4: 87 percent / NaOH / tetrahydrofuran; H₂O

With sodium hydroxide; 4-acetamidobenzenesulfonyl azide; iodine; triethylamine; triphenylphosphine; rhodium (II) octanoate dimer; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tet.2004.03.037

Reference yield:

methyl 3-(4-chlorophenyl)-2-diazo-3-oxopropanoate (6936-71-6) → 5-(4-chlorophenyl)oxazole-4-carboxylic acid (143659-14-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / dirhodium tetraoctanoate / CH₂Cl₂ / Heating

2: 65 percent / triphenylphosphine; iodine; triethylamine / CH₂Cl₂ / 16 h

3: 87 percent / NaOH / tetrahydrofuran; H₂O

With sodium hydroxide; iodine; triethylamine; triphenylphosphine; rhodium (II) octanoate dimer; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tet.2004.03.037

upstream raw materials:

5-(4-chlorophenyl)oxazole-4-carboxylic acid methyl ester

methyl 3-(4-chlorophenyl)-3-oxopropanoate

methyl 3-(4-chlorophenyl)-2-diazo-3-oxopropanoate

N-[2-(4-chlorophenyl)-1-methoxycarbonyl-2-oxoethyl]formamide

Downstream raw materials:

5-(4-chlorophenyl)oxazole-4-carboxamide

5-chlorophenyl-N-[1-methoxycarbonyl-2-oxopropyl]oxazole-4-carboxamide

Refernces

• 1、 Davies, James R.,Kane, Peter D.,Moody, Christopher J.. "N-H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles". . p. 3967 - 3977. Retrieved 2007/10/03.