Diethyl 5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate

Base Information

• Chemical Name: Diethyl 5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate
• CAS No.: 100129-92-8
• Molecular Formula: C11H14ClNO4
• Molecular Weight: 259.68600
• DSSTox Substance ID: DTXSID00450566
• Wikidata: Q82270352
• Mol file: 100129-92-8.mol

Synonyms:100129-92-8;Diethyl 5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate;1H-Pyrrole-2,4-dicarboxylic acid, 5-chloro-3-methyl-, diethyl ester;DTXSID00450566;SB63382;Diethyl5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate;5-Chloro-3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

Chemical Property of Diethyl 5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate

Chemical Property:

• PSA: 68.39000
• LogP: 2.32990
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 259.0611356
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

Diethyl5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C1C)C(=O)OCC)Cl

Technology Process of Diethyl 5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate

There total 6 articles about Diethyl 5-chloro-3-methyl-1H-pyrrole-2,4-dicarboxylate 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: 79.0%

diethyl 5-formyl-3-methylpyrrole-2,4-dicarboxylate (2199-60-2) → diethyl 5-chloro-3-methylpyrrole-2,4-dicarboxylate (100129-92-8)

Guidance literature:

With dichloromethane; chlorine; In water; acetic acid; for 0.0833333h; Heating;

Reference yield: 15.0%

diethyl 5-bromo-3-methylpyrrole-2,4-dicarboxylate (4458-69-9) → diethyl 5-chloro-3-methylpyrrole-2,4-dicarboxylate (100129-92-8)

Guidance literature:

With hydrogenchloride; In tetrachloromethane; at 80 ℃; for 144h;

Reference yield:

3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester (5448-16-8) → diethyl 5-chloro-3-methylpyrrole-2,4-dicarboxylate (100129-92-8) + 1-amino-3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester (427878-69-1)

Guidance literature:

3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester; With potassium tert-butylate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

With chloroamine; tert-butyl methyl ether; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; pH=3 - 4;

DOI:10.1021/jo035587p

upstream raw materials:

diethyl 5-bromo-3-methylpyrrole-2,4-dicarboxylate

diethyl 5-formyl-3-methylpyrrole-2,4-dicarboxylate

3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

1-amino-3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

Downstream raw materials:

4-ethoxycarbonyl-3-methylpyrrole-2-carboxylic acid

ethyl 4-methylpyrrole-3-carboxylate

methyl 4-methyl-1H-pyrrole-3-carboxylate

4-methyl-1H-pyrrole-3-carboxylic acid

Refernces

• 1、 Giuliano, Francesco,Penna, Marina,Sleiter, Giancarlo. "ELECTROPHILIC HETEROAROMATIC SUBSTITUTIONS. IX. BEHAVIOUR OF HALOGENOPYRROLES TOWARDS HYDROGEN HALIDES IN DIVERSE SOLVENTS". . p. 589 - 594. Retrieved 2007/10/02.