Ethyl crotonate

Base Information

• Chemical Name: Ethyl crotonate
• CAS No.: 623-70-1
• Deprecated CAS: 77825-56-0
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 29161980
• European Community (EC) Number: 234-125-9,210-808-7
• UN Number: 1862
• UNII: 99YUC7A1X1
• DSSTox Substance ID: DTXSID5057591
• Nikkaji Number: J161.352I,J43.537F
• Wikidata: Q1141618
• ChEMBL ID: CHEMBL3273403
• Mol file: 623-70-1.mol

Synonyms:ETHYL CROTONATE;623-70-1;10544-63-5;ethyl (E)-but-2-enoate;2-Butenoic acid, ethyl ester, (2E)-;Ethyl trans-2-butenoate;Ethyl (E)-crotonate;Ethyl trans-crotonate;2-Butenoic acid, ethyl ester;Crotonic acid, ethyl ester;ethyl (2E)-but-2-enoate;Crotonic acid, ethyl ester, (E)-;Ethyl (E)-2-butenoate;2-Butenoic acid, ethyl ester, (E)-;Ethyl 2-butenoate;Ethyl crotonate (E);FEMA No. 3486;trans-2-Butenoic acid ethyl ester;(E)-Ethyl but-2-enoate;Crotonate d'ethyle, (E)-;Ethyl 2-butenoate, (E)-;(E)-ethyl crotonate;(E)-2-Butenoic acid ethyl ester;NSC 4778;EINECS 210-808-7;EINECS 234-125-9;UN1862;Ethylester kyseliny krotonove [Czech];alpha-Crotonic acid ethyl ester, (E)-;BRN 0635834;BRN 1720418;Ethylester kyseliny krotonove;UNII-99YUC7A1X1;AI3-05622;99YUC7A1X1;Crotonic acid ethyl ester;(E)-but-2-enoic acid ethyl ester;Ethyl (2E)-2-butenoate;(E)-CH3CH=CHCOOC2H5;NSC4778;Crotonate d'thyle;Crotonic acid ethyl;Trans-ethylcrotonate;ethyl trans crotonate;Ethyl crotonate [UN1862] [Flammable liquid];Ethyl crotonate, 96%;Ethyl crotonate, 99%;Crotonate d'ethyle, E-;ethyl (E)-2-crotonate;crotonic-acid-ethyl-ester;Ethyl(E)-but-2-enoate;SCHEMBL24483;77825-56-0;Ethyl (2E)-2-butenoate #;ETHYL CROTONATE [FHFI];ETHYL-(E)-2-BUTENOATE;ETHYL-TRANS-2-BUTENOATE;CHEMBL3273403;DTXSID5057591;ETHYL TRANS-2-BUTENOATE-;CHEBI:173393;trans-but-2-enoic acid ethyl ester;BBL027753;MFCD00009289;NA1862;STL146343;AKOS005721070;CROTONIC ACID ETHYL ESTER [MI];ETHYL-(E)-2-BUTENOATE [FCC];LS-2717;Ethyl trans-2-butenoate, >=96%, FG;TRANS-2-BUTENOIC ACID ETHYLESTER;LS-55564;.alpha.-Crotonic acid ethyl ester, trans-;EN300-344919;Ethyl crotonate [UN1862] [Flammable liquid];Ethyl trans-2-butenoate, natural, >=97%, FG;A801242;A833743;J-502032;Q1141618;Z2327209524

Chemical Property of Ethyl crotonate

Chemical Property:

• Appearance/Colour: Colorless oily liquid with piquancy taste
• Vapor Pressure: 6.87mmHg at 25°C
• Melting Point: -79oC
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 137.999 °C at 760 mmHg
• Flash Point: 28.333 °C
• PSA: 26.30000
• Density: 0.915 g/cm³
• LogP: 1.12560
• Storage Temp.: Flammables area
• Water Solubility.: INSOLUBLE
• 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
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Ethyl Crotonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C,Xi
• Hazard Codes: F,C,Xi
• Statements: 11-34-36
• Safety Statements: 16-26-36/37/39-45-9-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C=CC
• Isomeric SMILES: CCOC(=O)/C=C/C
• Uses: Ethyl crotonate is used as a solvent for cellulose esters as well as a plasticizer for acrylic resins. Ethyl Crotonate is a synthetic flavoring agent that is a moderately stable, colorless to light yellow liquid of sharp winey note. it should be stored in glass, tin, or resin-lined containers. it is used in fruit flavors for application in baked goods, beverages, and candy at 2–7 ppm. Solvent and softening agent, lacquers, organic synthesis.

Technology Process of Ethyl crotonate

There total 65 articles about Ethyl crotonate 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: 98.0%

3-(ethylthio)-butanoic acid, ethyl ester (90201-28-8) → ethyl (E)-crotonate (623-70-1)

Guidance literature:

With tetrabutylammomium bromide; In ethanol; electrolysis;

DOI:10.1016/S0040-4039(00)84941-2

Reference yield: 97.0%

ethyl trans-2-methylthiirane carboxylate (107467-99-2) → ethyl (E)-crotonate (623-70-1)

Guidance literature:

di(rhodium)tetracarbonyl dichloride; In benzene; for 18h; under 20685.9 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(00)84852-2

Reference yield: 95.0%

fac-tricarbonyl{1-ethoxy-1-oxo-2-butenyl-C(3),O}(triphenylphosphine)rhenium → ethyl (E)-crotonate (623-70-1)

Guidance literature:

With CF₃CO₂H; In benzene-d6; React. at 25°C, 10 h.; Monitored by (1)H-NMR.;

DOI:10.1021/ja00163a038

upstream raw materials:

2-butenoic acid

ethanol

ethyl 3-hydroxybutyrate

trans-chrotonyl chloride

Downstream raw materials:

4-bromo-trans-crotonic acid ethyl ester

methyl-3 cyclohexyl-3 (oxo-2') propanoate d'ethyle

2-chloro-3-(4-chloro-phenyl)-butyric acid ethyl ester

3-methyl-4-nitrobutyric acid ethyl ester

Refernces

• 1、 Liu, Feng,Liu, Jia-Li,tu, Jia-Lin. "Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors". supporting information. p. 7369 - 7372. Retrieved 2020/10/05.
• 2、 Zuo, Ya-Jie,Chang, Xiao-Tong,Hao, Zhi-Ming,Zhong, Chong-Min. "Copper-catalyzed, stereoconvergent,: Cis -diastereoselective borylative cyclization of ω -mesylate- α, β -unsaturated esters and ketones". supporting information. p. 6323 - 6327. Retrieved 2017/08/10.