Ethyl 3-ethoxy-2-butenoate

Base Information

• Chemical Name: Ethyl 3-ethoxy-2-butenoate
• CAS No.: 57592-45-7
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• European Community (EC) Number: 213-652-8,610-985-4,620-908-6
• NSC Number: 224119,2321
• UNII: 28C6ULL9XY
• DSSTox Substance ID: DTXSID8075174,DTXSID501303315
• Nikkaji Number: J1.576.792H
• Mol file: 57592-45-7.mol

Synonyms:Ethyl 3-ethoxy-2-butenoate;998-91-4;Ethyl 3-ethoxy-cis-crotonate;Ethyl 3-ethoxybut-2-enoate;2-Butenoic acid, 3-ethoxy-, ethyl ester, (2E)-;5331-73-7;ethyl (E)-3-ethoxybut-2-enoate;57592-45-7;ethyl trans-3-ethoxycrotonate;2-Butenoic acid, 3-ethoxy-, ethyl ester;Ethyl (2E)-3-ethoxy-2-butenoate;NSC-2321;EINECS 213-652-8;NSC-224119;AI3-05594;Crotonic acid, 3-ethoxy-, ethyl ester;ethyl beta-ethoxycrotonate;ethyl (2E)-3-ethoxybut-2-enoate;(E)-ethyl 3-ethoxybut-2-enoate;(Z)-Ethyl 3-ethoxybut-2-enoate;3-Ethoxycrotonic acid ethyl ester;ethyl (2Z)-3-ethoxy-2-butenoate;MFCD00026932;Ethyl3-ethoxy-2-butenoate;28C6ULL9XY;Ethyl (E)-3-ethoxycrotonate;ethyl (E)-3-ethoxy-crotonate;SCHEMBL9639948;DTXSID8075174;NSC2321;DTXSID501303315;NSC 2321;NSC224119;beta-Ethoxy-cronoic acid, ethyl ester;AKOS009157043;2-Butenoic acid,3-ethoxy-,ethyl ester;NSC 224119;(E)-3-ethoxy-crotonic acid ethyl ester;Ethyl 3-ethoxy-2-butenoate, AldrichCPR;CS-12474;(2E)-3-Ethoxy-2-butenoic acid ethyl ester;(2E)-3-Ethoxybut-2-enoic acid ethyl ester;CS-0250815;EN300-52315;A916249;Z740905622

Chemical Property of Ethyl 3-ethoxy-2-butenoate

Chemical Property:

• Melting Point: 30-32 °C(lit.)
• Refractive Index: 1.4290 (estimate)
• Boiling Point: 195-200 °C(lit.)
• Flash Point: 137 °F
• PSA: 35.53000
• Density: 1.0543 (rough estimate)
• LogP: 1.48980
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Ethyl3-ethoxybut-2-enoate 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=CC(=O)OCC)C
• Isomeric SMILES: CCO/C(=C/C(=O)OCC)/C

Technology Process of Ethyl 3-ethoxy-2-butenoate

There total 7 articles about Ethyl 3-ethoxy-2-butenoate 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: 54.0%

diethyl sulfate (64-67-5) + enolate potassique de l'acetylacetate d'ethyle → ethyl (Z)-3-ethoxybut-2-enoate (5331-73-7) + ethyl (E)-3-ethoxy-2-butenoate (57592-45-7) + ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

With polymer-HMPT; In tetrahydrofuran; at 20 ℃; for 24h; Yields of byproduct given;

DOI:10.1016/0040-4020(82)85033-3

Reference yield: 2.0%

ethyl bromide (74-96-4) + 18-crown-6 ether (17455-13-9) + acetoacetic acid ethyl ester; potassium (Z)-enolate (66279-50-3) + [2.2.2]cryptande (23978-09-8) → ethyl (Z)-3-ethoxybut-2-enoate (5331-73-7) + ethyl (E)-3-ethoxy-2-butenoate (57592-45-7) + ethyl 2,2-diethyl-3-oxobutanoate (1619-57-4) + ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

In 1,2-dimethoxyethane; at 40 ℃; Mechanism; Product distribution;

DOI:10.1016/0040-4020(80)80058-5

Reference yield:

diethyl sulfate (64-67-5) + enolate lithique de l'acetylacetate d'ethyle → ethyl (Z)-3-ethoxybut-2-enoate (5331-73-7) + ethyl (E)-3-ethoxy-2-butenoate (57592-45-7) + ethyl 2-ethyl-3-oxobutanoate (607-97-6)

Guidance literature:

With copolymere de N-vinylpyrrolidone et de divinylbenzene; In tetrahydrofuran; at 20 ℃; for 72h; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4020(82)85033-3

upstream raw materials:

ethyl bromide

acetoacetic acid ethyl ester; potassium (Z)-enolate

diethyl sulfate

ethyl ester of p-toluenesulfonic acid

Downstream raw materials:

4-bromo-3-ethoxy-2-butenoic acid ethyl ester

3-ethoxy-5-phenyl-hexa-2c,4t-dienoic acid

3-ethoxy-5-phenyl-hexa-2c,4c-dienoic acid

2-(p-Isobutylphenyl)-2-penten-4-on