5-[(5-carboxy-3-ethoxycarbonyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-ethox ycarbonyl-3-methyl-1H-pyrrole-2-carboxylic acid

Base Information

• Chemical Name: 5-[(5-carboxy-3-ethoxycarbonyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-ethox ycarbonyl-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS No.: 6305-92-6
• Molecular Formula: C₁₉H₂₂N₂O₈
• Molecular Weight: 406.392
• Hs Code.: 2933990090
• Mol file: 6305-92-6.mol

Synonyms:Pyrrole-2,4-dicarboxylicacid, 5,5'-methylenebis[3-methyl-, 4,4'-diethyl ester (7CI); NSC 22706

Chemical Property of 5-[(5-carboxy-3-ethoxycarbonyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-ethox ycarbonyl-3-methyl-1H-pyrrole-2-carboxylic acid

Chemical Property:

• Boiling Point: 752.7oC at 760 mmHg
• Flash Point: 409oC
• PSA: 158.78000
• Density: 1.392g/cm3
• LogP: 2.30020

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-[(5-carboxy-3-ethoxycarbonyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-ethox ycarbonyl-3-methyl-1H-pyrrole-2-carboxylic acid

There total 5 articles about 5-[(5-carboxy-3-ethoxycarbonyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-ethox ycarbonyl-3-methyl-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: 39.0%

ethyl 2-(chloromethyl)-3-(ethoxycarbonyl)-4-methylpyrrole-5-carboxylate (5408-12-8) → 3,3'-bisethoxycarbonyl-4,4'-dimethyl-2,2'-dipyrrolylmethane-5,5'-dicarboxylic acid (6305-92-6)

Guidance literature:

With potassium hydroxide; for 3h; Heating;

DOI:10.1039/P19810002656

Reference yield:

<3,3',5,5'-tetrakis(ethoxycarbonyl)-4,4'-dimethyl-2,2'-dipyrryl>methane (5431-96-9) → 3,3'-bisethoxycarbonyl-4,4'-dimethyl-2,2'-dipyrrolylmethane-5,5'-dicarboxylic acid (6305-92-6)

Guidance literature:

With sodium carbonate;

DOI:10.1021/ja01157a128

Reference yield:

diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate (2436-79-5) → 3,3'-bisethoxycarbonyl-4,4'-dimethyl-2,2'-dipyrrolylmethane-5,5'-dicarboxylic acid (6305-92-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 42 percent / bromine / acetic acid / 0.5 h / 40 - 43 °C

2: 50 percent / aq. HBr / methanol / 7 h / Heating

3: NaOH / ethanol; H₂O / 3 h / Heating

With sodium hydroxide; hydrogen bromide; bromine; In methanol; ethanol; water; acetic acid;

DOI:10.1002/jhet.5570280707

upstream raw materials:

<3,3',5,5'-tetrakis(ethoxycarbonyl)-4,4'-dimethyl-2,2'-dipyrryl>methane

ethyl 2-(chloromethyl)-3-(ethoxycarbonyl)-4-methylpyrrole-5-carboxylate

diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate

diethyl 5-(bromomethyl)-3-methylpyrrole-2,4-dicarboxylate

Downstream raw materials:

3,7-bis(ethoxycarbonyl)-2,8-dimethyl-dipyrromethane

Refernces

• 1、 Brittain, Judith M.,Jones, R. Alan,Jones, Richard O.,King, Trevor J.. "Pyrrole Studies. Part 26. A Novel Thermochromic and Photochromic Pyrrole System". . p. 2656 - 2661. Retrieved 2007/10/02.