Ethyl 3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

Base Information

• Chemical Name: Ethyl 3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate
• CAS No.: 2769-90-6
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80698681
• Mol file: 2769-90-6.mol

Synonyms:SCHEMBL9267870;DTXSID80698681;Ethyl 3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

Chemical Property of Ethyl 3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

Chemical Property:

• Vapor Pressure: 0.0026mmHg at 25°C
• Refractive Index: 1.495
• Boiling Point: 286.7°C at 760 mmHg
• PKA: -3.97±0.70(Predicted)
• Flash Point: 127.2°C
• PSA: 31.23000
• Density: 1g/cm³
• LogP: 1.60140
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 201

Purity/Quality:

99%min ^*data from raw suppliers

3-(1-METHYL-1H-PYRROL-2-YL)-ACRYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=CN1C

Technology Process of Ethyl 3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate

There total 5 articles about Ethyl 3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate 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: 84.0%

1-methyl-2-pyrrolyl chloride (56454-26-3) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (2E)-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate (2769-90-6)

Guidance literature:

With potassium phosphate; Pd((CH₃)2C₆H₃NC(CH₃)CHC(CH₃)NC₆H₃(CH₃)2)(CH₃)(P(CH₂CH₃)3); tetrabutylammomium bromide; In water; N,N-dimethyl-formamide; at 100 ℃; for 8h; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ol202177k

Reference yield: 84.0%

N-methylpyrrole aldehyde (1192-58-1) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl (2E)-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate (2769-90-6)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h;

N-methylpyrrole aldehyde; In tetrahydrofuran; at 22 ℃; for 48h;

Reference yield: 78.0%

N-methylpyrrole aldehyde (1192-58-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (2E)-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate (2769-90-6)

Guidance literature:

In ethanol; at 80 ℃;

DOI:10.1016/j.bmcl.2017.08.051

upstream raw materials:

N-methylpyrrole aldehyde

diethoxyphosphoryl-acetic acid ethyl ester

1-methyl-2-pyrrolyl chloride

ethyl acrylate

Downstream raw materials:

(2E)-3-[5-[(1E)-3-(3-fluorophenyl)-3-oxo-1-propen-1-yl]-1-methyl-1H-pyrrol-2-yl]-N-hydroxy-2-propenamide

3-[1-methyl-4-(3-oxo-3-o-tolyl-propenyl)-1H-pyrrol-2-yl]-acrylic acid

(E)-3-{4-[(E)-3-(3-Chloro-phenyl)-3-oxo-propenyl]-1-methyl-1H-pyrrol-2-yl}-acrylic acid

3-[1-methyl-4-(3-oxo-3-p-tolyl-propenyl)-1H-pyrrol-2-yl]-acrylic acid

Refernces

• 1、 -. "COMPOSITIONS AND METHODS FOR TREATING EPIGENETIC DISEASE". Page/Page column 29-30. . Retrieved 2020/02/16.
• 2、 Chen, Dong-Dong,Zhang, Bing-Yu,Liu, Xiu-Xiu,Li, Xing-Qiang,Yang, Xin-Juan,Zhou, Le. "Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi". supporting information. p. 1149 - 1153. Retrieved 2018/03/05.