ethyl (2Z)-but-2-enoate

Base Information

• Chemical Name: ethyl (2Z)-but-2-enoate
• CAS No.: 6776-19-8
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 2916190090
• NSC Number: 4778
• DSSTox Substance ID: DTXSID301315530
• Nikkaji Number: J17.378I
• Wikidata: Q27159537
• Metabolomics Workbench ID: 48580
• Mol file: 6776-19-8.mol

Synonyms:cis-Ethyl crotonate;ethyl (2Z)-but-2-enoate;6776-19-8;Ethyl (Z)-2-butenoate;2-Butenoic acid, ethyl ester, (Z)-;2-Butenoic acid, ethyl ester;ethyl cis-crotonate;Ethyl (2E)-2-butenoate;(Z)-ethyl but-2-enoate;(E)-CH3CH=CHCOOC2H5;NSC4778;ethyl isocrotonate;Ethyl crotonate [UN1862] [Flammable liquid];(E)-Ethyl 2-butenoate;Ethyl ester(e)-Crotonic acid;SCHEMBL264867;alpha -crotonic acid ethyl ester;CHEBI:87334;Ethyl ester(E)-2-Butenoic acid;FEMA 3486;(Z)-2-Butenoic acid ethyl ester;cis-but-2-enoic acid ethyl ester;DTXSID301315530;Ethyl ester(2E)-2-Butenoic acid;NSC-4778;(e)-alpha-crotonic acid ethyl ester;LMFA07010875;2-Butenoic acid, ethyl ester, (E)- (9CI);Q27159537

Chemical Property of ethyl (2Z)-but-2-enoate

Chemical Property:

• Melting Point: 37.22°C (estimate)
• Refractive Index: 1.4242
• Boiling Point: 123.66°C (estimate)
• PSA: 26.30000
• Density: 0.9182
• LogP: 1.12560
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 94.7

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C=CC
• Isomeric SMILES: CCOC(=O)/C=C\C

Technology Process of ethyl (2Z)-but-2-enoate

There total 14 articles about ethyl (2Z)-but-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: 91.0%

Ethyl 2-butynoate (4341-76-8) → ethyl (Z)-crotonate (6776-19-8)

Guidance literature:

With hydrogen; In ethanol; at 50 ℃; for 5h; under 760.051 Torr;

DOI:10.1021/acscatal.5b02518

Reference yield: 53.0%

ethyl α-ethyldiazoacetate (107445-16-9) + phenylacetylene (536-74-3) → ethyl (Z)-crotonate (6776-19-8) + (+)-ethyl 2-phenyl-1-ethylcycloprop-2-ene-1-carboxylate + (-)-ethyl 2-phenyl-1-ethylcycloprop-2-ene-1-carboxylate

Guidance literature:

With dirhodium(II) tetrakis[N-tetrabromophthaloyl-(S)-tert-leucinate] dihydrate; In dichloromethane; at -60 ℃; for 0.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201101905

Reference yield: 40.0%

carbon monoxide (201230-82-2) + sodium ethanolate (141-52-6) + 3-chloroprop-1-ene (107-05-1) → ethyl (Z)-crotonate (6776-19-8) + ethyl 3-butenoate (1617-18-1)

Guidance literature:

With dicobalt octacarbonyl; tetra-(n-butyl)ammonium iodide; In benzene; at 25 ℃; for 6h;

upstream raw materials:

ethyl 3-butenoate

Vinyl bromide

bromo(2-ethoxy-2-oxoethyl)zinc

Ethyl 2-butynoate

Downstream raw materials:

7-Methyl-5-oxo-1,2,3,5,6,7-hexahydro-indolizine-8-carboxylic acid ethyl ester

ethyl 3-(benzylamino)butanoate

ethyl (E)-crotonate

Refernces

• 1、 Fernandes, Alessandra A. G.,Leonarczyk, Ives A.,Ferreira, Marco A. B.,Dias, Luiz Carlos. "Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones". supporting information. p. 3167 - 3180. Retrieved 2019/03/26.
• 2、 Ji, Guijie,Duan, Yanan,Zhang, Shaochun,Fei, Benhua,Chen, Xiufang,Yang, Yong. "Selective Semihydrogenation of Alkynes Catalyzed by Pd Nanoparticles Immobilized on Heteroatom-Doped Hierarchical Porous Carbon Derived from Bamboo Shoots". . p. 3427 - 3434. Retrieved 2017/09/15.