(E)-ethyl 3-(pyridin-3-yl)acrylate

Base Information

• Chemical Name: (E)-ethyl 3-(pyridin-3-yl)acrylate
• CAS No.: 28447-17-8
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.2
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID50905036
• Nikkaji Number: J591.423J,J863.349E
• Wikidata: Q81988360
• ChEMBL ID: CHEMBL2289662
• Mol file: 28447-17-8.mol

Synonyms:28447-17-8;(E)-ethyl 3-(pyridin-3-yl)acrylate;59607-99-7;ETHYL 3-(3-PYRIDYL)ACRYLATE;ethyl (E)-3-(3-pyridinyl)-2-propenoate;ETHYL 3-(PYRIDIN-3-YL)ACRYLATE;3-Pyridineacrylic acid ethyl ester;ethyl (E)-3-pyridin-3-ylprop-2-enoate;ETHYL 3-PYRIDINEACRYLATE;ethyl (2E)-3-(pyridin-3-yl)prop-2-enoate;Ethyl 3-(3-pyridyl)propenoate;Ethyl-3-pyridine acrylate;SCHEMBL533790;CHEMBL2289662;DTXSID50905036;ethyl trans-3-(3-pyridyl)acrylate;Pyridine-3-acrylic acid ethyl ester;(E)-ethyl3-(pyridin-3-yl)acrylate;MFCD02177443;AKOS005072199;CE-0210;(E)-3-Pyridineacrylic acid ethyl ester;CS-0088304;Ethyl (2E)-3-(3-pyridinyl)-2-propenoate #;W11611;EN300-1455928;A853261;J-502030;W-203225

Chemical Property of (E)-ethyl 3-(pyridin-3-yl)acrylate

Chemical Property:

• Vapor Pressure: 0.00322mmHg at 25°C
• Refractive Index: 1.553
• Boiling Point: 285.2 °C at 760 mmHg
• Flash Point: 126.3 °C
• PSA: 39.19000
• Density: 1.106 g/cm³
• LogP: 1.65790
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl(E)-3-(3-Pyridinyl)-2-propenoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CN=CC=C1
• Isomeric SMILES: CCOC(=O)/C=C/C1=CN=CC=C1

Technology Process of (E)-ethyl 3-(pyridin-3-yl)acrylate

There total 40 articles about (E)-ethyl 3-(pyridin-3-yl)acrylate 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: 100.0%

3-pyridinecarboxaldehyde (500-22-1) + (ethoxycarbonylmethyl)triphenylphosphonium chloride (17577-28-5) → 3-(pyridin-3-yl)acrylic acid ethyl ester (28447-17-8)

Guidance literature:

(ethoxycarbonylmethyl)triphenylphosphonium chloride; With sodium hydride; In tetrahydrofuran; mineral oil; for 1h; Inert atmosphere; Reflux;

3-pyridinecarboxaldehyde; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;

With sulfuric acid; In acetone; for 6h; Reflux;

DOI:10.1016/j.bmc.2009.01.023

Reference yield: 99.0%

3-pyridinecarboxaldehyde (500-22-1) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl (E)-3-(pyridin-3-yl)acrylate (59607-99-7,28447-17-8)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at -40 - 20 ℃;

3-pyridinecarboxaldehyde; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b508634e

Reference yield: 99.0%

3-Bromopyridine (626-55-1,163928-56-1) + ethyl acrylate (140-88-5,9003-32-1) → 3-(pyridin-3-yl)acrylic acid ethyl ester (28447-17-8)

Guidance literature:

With potassium phosphate; [((ferrocenyl)(C(CH₃)N(C₆H₄)CH₃))PdCl(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)]; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 140 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.040

upstream raw materials:

(E)-3-(2-pyridyl)acrylic acid

3-pyridinecarboxaldehyde

diethoxyphosphoryl-acetic acid ethyl ester

ethyl acetate

Downstream raw materials:

(R,S)-1-{3(R)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}-2-[(4-chlorophenoxy)methyl]-4-({3(S)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}oxy)benzimidazole

(R,R)-1-{3(R)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}-2-[(4-chlorophenoxy)methyl]-4-({3(R)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}oxy)benzimidazole

(S,S)-1-{3(S)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}-2-[(4-chlorophenoxy)methyl]-4-({3(S)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}oxy)benzimidazole

(S,R)-1-{3(S)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}-2-[(4-chlorophenoxy)methyl]-4-({3(R)-[N-(tert-butyloxycarbonyl)-3-piperidinyl]propyl}oxy)benzimidazole

Refernces

• 1、 Falkner,Harrison. "-". . p. 2148. Retrieved 1962.
• 2、 Li, Gongming,Guo, Qingqing,Feng, Chao,Chen, Huan,Zhao, Wenjiao,Li, Shu,Hong, Yang,Sun, Dequn. "Synthesis of oxadiazole-2-oxide derivatives as potential drug candidates for schistosomiasis targeting SjTGR". . . Retrieved 2021/05/03.
• 3、 Baumann, Andreas N.,Dechent, Jonas,Didier, Dorian,Jagau, Thomas C.,Müller, Nicolas,Music, Arif. "Electro-Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes". supporting information. . Retrieved 2020/07/04.