Propenoic acid, 3-(5-ethoxycarbonyl-2,4-dimethyl-3-pyrrolyl)-

Base Information

• Chemical Name: Propenoic acid, 3-(5-ethoxycarbonyl-2,4-dimethyl-3-pyrrolyl)-
• CAS No.: 52649-02-2
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.255
• NSC Number: 157277
• DSSTox Substance ID: DTXSID50418792
• Wikidata: Q82229478
• Mol file: 52649-02-2.mol

Synonyms:NSC157277;52649-02-2;DTXSID50418792;MMLQKGNQOPYPBE-AATRIKPKSA-N;NSC-157277;Propenoic acid, 3-(5-ethoxycarbonyl-2,4-dimethyl-3-pyrrolyl)-;(2E)-3-[5-(Ethoxycarbonyl)-2,4-dimethyl-1H-pyrrol-3-yl]-2-propenoic acid #;1H-Pyrrole-2-carboxylic acid, 4-(2-carboxyethenyl)-3,5-dimethyl-, 2-ethyl ester

Chemical Property of Propenoic acid, 3-(5-ethoxycarbonyl-2,4-dimethyl-3-pyrrolyl)-

Chemical Property:

• Vapor Pressure: 5.69E-08mmHg at 25°C
• Boiling Point: 424.7°C at 760 mmHg
• Flash Point: 210.7°C
• Density: 1.246g/cm³
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 327

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Propenoic acid, 3-(5-ethoxycarbonyl-2,4-dimethyl-3-pyrrolyl)-

There total 1 articles about Propenoic acid, 3-(5-ethoxycarbonyl-2,4-dimethyl-3-pyrrolyl)- 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 3,5-dimethyl-4-formyl-1H-pyrrole-2-carboxylate (2199-64-6) + malonic acid (141-82-2) → 5-ethoxycarbonyl-2,4-dimethylpyrrole-3-acrylic acid (52649-02-2)

Guidance literature:

With pyridine;

Reference yield: 90.0%

5-ethoxycarbonyl-2,4-dimethylpyrrole-3-acrylic acid (52649-02-2) → 4-(2-carboxyethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (37789-64-3)

Guidance literature:

With hydrogen; nickel; In sodium hydroxide; for 12h; under 1551.4 Torr; Ambient temperature;

DOI:10.1016/0040-4020(90)80003-Z

Reference yield:

5-ethoxycarbonyl-2,4-dimethylpyrrole-3-acrylic acid (52649-02-2) → ethyl 4-methyl-1H-pyrrole-3-propanoate (132281-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / H₂ / Raney nickel / aq. NaOH / 12 h / 1551.4 Torr / Ambient temperature

2: 88 percent / SO₂Cl₂ / diethyl ether / -15 deg C, 1h, then 0 deg C, 4h

3: 1.) 10percent aq. NaOH / 1.) 180 deg C, 90 min, 2.) EtOH, ether

With sodium hydroxide; sulfuryl dichloride; hydrogen; nickel; In sodium hydroxide; diethyl ether;

DOI:10.1016/0040-4020(90)80003-Z

upstream raw materials:

ethyl 3,5-dimethyl-4-formyl-1H-pyrrole-2-carboxylate

malonic acid

Downstream raw materials:

4-(2-carboxyethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

ethyl 4-methyl-1H-pyrrole-3-propanoate

ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate

ethyl 5-(ethoxycarbonyl)-2,4-dimethyl-1H-pyrrole-3-propanoate