4'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

Base Information

• Chemical Name: 4'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid
• CAS No.: 1000587-29-0
• Molecular Formula: C14H11NO4
• Molecular Weight: 257.246
• Hs Code.: 2916399090
• Mol file: 1000587-29-0.mol

Synonyms:4'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid;3-(4-Methylphenyl)-5-nitrobenzoic acid

Chemical Property of 4'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

Chemical Property:

• PSA: 83.12000
• LogP: 3.79160
• Storage Temp.: 2-8°C

Purity/Quality:

95+% ^*data from raw suppliers

4''-Methyl-5-nitro-[1,1''-biphenyl]-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

There total 5 articles about 4'-Methyl-5-nitro-[1,1'-biphenyl]-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: 98.0%

3-iodo-5-nitro-benzoic acid (6313-17-3) + 4-methylphenylboronic acid (5720-05-8) → 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (1000587-29-0)

Guidance literature:

3-iodo-5-nitro-benzoic acid; 4-methylphenylboronic acid; With caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; toluene; for 18h; Heating / reflux;

With hydrogenchloride; water; pH=< 4;

Reference yield:

3-bromo-5-nitro-benzoic acid (6307-83-1) → 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (1000587-29-0)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 3 h / Reflux

2: caesium carbonate; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / water; toluene; ethanol / 24 h / Reflux

3: potassium hydroxide; water / tetrahydrofuran / 3 h / Reflux

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; thionyl chloride; water; caesium carbonate; potassium hydroxide; In tetrahydrofuran; ethanol; water; toluene;

DOI:10.1016/j.tet.2020.131063

Reference yield:

3-nitrobenzoic acid (121-92-6) → 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (1000587-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfur trioxide; iodine; sulfuric acid / sulfuric acid / 14 h / 20 - 85 °C

2.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 18 h / 20 °C / Reflux

2.2: 0.5 h / 20 °C

2.3: pH 4

With sulfuric acid; sulfur trioxide; iodine; caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; sulfuric acid; water; toluene;

upstream raw materials:

3-iodo-5-nitro-benzoic acid

4-methylphenylboronic acid

3-nitrobenzoic acid

3-bromo-5-nitro-benzoic acid

Downstream raw materials:

4′-methyl-5-(5-methyltetrazol-1-yl)-biphenyl-3-carboxylic acid

4′-methyl-5-(5-methyltetrazol-1-yl)biphenyl-3-carboxylic acid methyl ester

4′-methyl-5-(5-trifluoromethyltetrazol-1-yl)biphenyl-3-carboxylic acid

4′-methyl-5-(5-trifluoromethyltetrazol-1-yl)biphenyl-3-carboxylic acid methyl ester

Refernces

• 1、 Ma, Jun-An,Peng, Xing,Xiao, Ming-Yang,Xue, Xiao-Song,Zhang, Fa-Guang,Zheng, Meng-Meng. "Catalytic Direct Construction of Cyano-tetrazoles". . p. 7762 - 7767. Retrieved 2020/10/09.
• 2、 -. "THIAZOLE AND OXAZOLE-SUBSTITUTED ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS". Page/Page column 33-34. . Retrieved 2012/02/03.