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

Base Information

• Chemical Name: Diethyl 3-methyl-1H-pyrrole-2,5-dicarboxylate
• CAS No.: 29170-87-4
• Molecular Formula: C₁₁H₁₅NO₄
• Molecular Weight: 225.244
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90342789
• Nikkaji Number: J121.892A
• Wikidata: Q82113758
• Mol file: 29170-87-4.mol

Synonyms:29170-87-4;Diethyl 3-methyl-1H-pyrrole-2,5-dicarboxylate;3-Methyl-pyrrole-2,5-dicarboxylic acid diethyl ester;3-methyl-1H-pyrrole-2,5-dicarboxylic acid diethyl ester;1H-Pyrrole-2,5-dicarboxylic acid, 3-methyl-, diethyl ester;SCHEMBL11191069;DTXSID90342789;AKOS015900351;diethyl 3-methylpyrrole-2,5-dicarboxylate;FT-0651925;A819793;Diethyl 3-methyl-1H-pyrrole-2,5-dicarboxylate #

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

Chemical Property:

• Melting Point: 61 °C
• Boiling Point: 344.8±37.0 °C(Predicted)
• PKA: 13.79±0.50(Predicted)
• PSA: 68.39000
• Density: 1.168±0.06 g/cm3(Predicted)
• LogP: 1.67650
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 225.10010796
• Heavy Atom Count: 16
• Complexity: 267

Purity/Quality:

97% ^*data from raw suppliers

3-METHYL-PYRROLE-2,5-DICARBOXYLIC ACID DIETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=C(N1)C(=O)OCC)C

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

There total 7 articles about Diethyl 3-methyl-1H-pyrrole-2,5-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:

ethyl 2-amino-3-oxobutanoate hydrochloride (20207-16-3) + ethyl 2,4-diketopentanoate (615-79-2) → diethyl 3-methyl-pyrrole-2,5-dicarboxylate (29170-87-4) + <2,4-Dimethyl-5-ethoxycarbonyl-pyrryl-(3)>-glyoxylsaeureester (21898-53-3)

Guidance literature:

With sodium acetate; acetic acid;

DOI:10.1093/pa/53.3.443

Reference yield:

3-bromo-4-methyl-pyrrole-2,5-dicarboxylic acid diethyl ester (857420-93-0) → diethyl 3-methyl-pyrrole-2,5-dicarboxylate (29170-87-4)

Guidance literature:

With methanol; coal catalyst; magnesium oxide; palladium; Hydrogenation;

DOI:10.1021/ja01184a037

Reference yield:

ethyl 4-bromo-3,5-dimethylpyrrole-2-carboxylate (5408-07-1) → diethyl 3-methyl-pyrrole-2,5-dicarboxylate (29170-87-4)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; bromine / anschliessendes Behandeln mit SO₂Cl₂ und Erwaermen des erhaltenen Reaktionsgemisches mit H₂O

2: ethanolic KOH

3: palladium/ magnesium oxide / coal catalyst; methanol / Hydrogenation

With methanol; potassium hydroxide; coal catalyst; bromine; magnesium oxide; palladium; acetic acid;

DOI:10.1021/ja01184a037

upstream raw materials:

Diazoethan

5-(ethoxycarbonyl)-3-methyl-1H-pyrrole-2-carboxylic acid

3-bromo-4-methyl-pyrrole-2,5-dicarboxylic acid diethyl ester

ethyl 2-amino-3-oxobutanoate hydrochloride

Downstream raw materials:

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

ethyl 3-methyl-1H-pyrrole-2-carboxylate

Refernces