1-(2-Carboxy-4-chlorophenyl)-1H-pyrrole-2-carboxylic acid

Base Information

• Chemical Name: 1-(2-Carboxy-4-chlorophenyl)-1H-pyrrole-2-carboxylic acid
• CAS No.: 354115-82-5
• Molecular Formula: C₁₂H₈ClNO₄
• Molecular Weight: 265.653
• DSSTox Substance ID: DTXSID601195577
• Nikkaji Number: J1.527.717C
• Mol file: 354115-82-5.mol

Synonyms:1-(2-Carboxy-4-chlorophenyl)-1H-pyrrole-2-carboxylic acid;DTXSID601195577;354115-82-5

Chemical Property of 1-(2-Carboxy-4-chlorophenyl)-1H-pyrrole-2-carboxylic acid

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 265.0141854
• Heavy Atom Count: 18
• Complexity: 349

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CN(C(=C1)C(=O)O)C2=C(C=C(C=C2)Cl)C(=O)O

Technology Process of 1-(2-Carboxy-4-chlorophenyl)-1H-pyrrole-2-carboxylic acid

There total 2 articles about 1-(2-Carboxy-4-chlorophenyl)-1H-pyrrole-2-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: 70.0%

1-(4-chlorophenyl)-1H-pyrrole (5044-38-2) + carbon dioxide (124-38-9,18923-20-1) → 1-(2-Carboxy-4-chlorophenyl)pyrrole-2-carboxylic acid (354115-82-5)

Guidance literature:

1-(4-chlorophenyl)-1H-pyrrole; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at 0 ℃; for 1h;

carbon dioxide; In tetrahydrofuran; diethyl ether; at 20 ℃; Further stages.;

DOI:10.1039/b100008j

Reference yield:

4-chloro-aniline (106-47-8) → 1-(2-Carboxy-4-chlorophenyl)pyrrole-2-carboxylic acid (354115-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / acetic acid

2.1: BuLi; TMEDA / diethyl ether / 1 h / 0 °C

2.2: 70 percent / tetrahydrofuran; diethyl ether / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; acetic acid;

DOI:10.1039/b100008j

Reference yield:

1-(2-Carboxy-4-chlorophenyl)pyrrole-2-carboxylic acid (354115-82-5) → 1-[4-Chloro-2-(hydroxymethyl)phenyl]-2-(hydroxymethyl)pyrrole (88442-99-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 25 ℃; for 10.5h;

DOI:10.1039/b100008j

upstream raw materials:

1-(4-chlorophenyl)-1H-pyrrole

carbon dioxide

4-chloro-aniline

Downstream raw materials:

1-[4-Chloro-2-(hydroxymethyl)phenyl]-2-(hydroxymethyl)pyrrole