Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate

Base Information

• Chemical Name: Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate
• CAS No.: 851195-35-2
• Molecular Formula: C17H17 Br N2 O2
• Molecular Weight: 361.238
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40581267
• Wikidata: Q82472336
• Mol file: 851195-35-2.mol

Synonyms:851195-35-2;ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate;ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methylpyrrole-2-carboxylate;3-(4-bromo-phenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylic acid ethyl ester;SCHEMBL4372272;DTXSID40581267;JNGAPOXDIKOBTD-UHFFFAOYSA-N;SB62443;A841224;ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-pyrrole-2-carboxylate;3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-2-pyrrolecarboxylic acid ethyl ester;Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1 H-pyrrole-2-carboxylate;ETHYL3-(4-BROMOPHENYL)-4-CYANO-5-ETHYL-1-METHYL-1H-PYRROLE-2-CARBOXYLATE

Chemical Property of Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate

Chemical Property:

• Vapor Pressure: 3.52E-10mmHg at 25°C
• Refractive Index: 1.586
• Boiling Point: 501.3°C at 760 mmHg
• Flash Point: 257°C
• PSA: 55.02000
• Density: 1.33g/cm³
• LogP: 4.06538
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 360.04734
• Heavy Atom Count: 22
• Complexity: 439

Purity/Quality:

97% ^*data from raw suppliers

Ethyl3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C(C(=C(N1C)C(=O)OCC)C2=CC=C(C=C2)Br)C#N

Technology Process of Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate

There total 6 articles about Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate 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: 98.3%

3-(4-bromophenyl)-4-cyano-5-ethyl-1H-pyrrole-2-carboxylic acid ethyl ester + methyl iodide (74-88-4) → 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (851195-35-2)

Guidance literature:

With potassium carbonate; In water; acetone; at 30 ℃; for 14h; Industry scale;

Reference yield: 63.0%

4-Bromophenylboronic acid (5467-74-3) → 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (851195-35-2)

Guidance literature:

4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester; With triphenylphosphine; palladium diacetate; In n-heptane; at 20 - 80 ℃;

4-Bromophenylboronic acid; With sodium carbonate; In n-heptane; water; at 84.5 ℃; for 5.5h;

Reference yield:

para-bromoacetophenone (99-90-1) → 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (851195-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / tetrahydrofuran / 4 h / 15 - 38 °C / Inert atmosphere

2.1: sodium nitrite / tetrahydrofuran; acetic acid; water / 3 h / 6 - 9 °C / Large scale

3.1: zinc / acetic acid; water; ethanol / 2.25 h / -5 - 20 °C / Inert atmosphere

3.2: 16 h / -9 - 20 °C

4.1: potassium carbonate / water; acetone / 4.2 h / 30 - 34.1 °C / Inert atmosphere

With potassium tert-butylate; potassium carbonate; zinc; sodium nitrite; In tetrahydrofuran; ethanol; water; acetic acid; acetone;

DOI:10.1021/op060104f

upstream raw materials:

methyl iodide

4-Bromophenylboronic acid

carbonic acid dimethyl ester

para-bromoacetophenone

Downstream raw materials:

4-cyano-5-ethyl-1-methyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-pyrrole-2-carboxylic acid ethyl ester