2-Butenoic acid, ethyl ester

Base Information

• Chemical Name: 2-Butenoic acid, ethyl ester
• CAS No.: 10544-63-5
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 29161900
• DSSTox Substance ID: DTXSID8065119
• Wikidata: Q81991999
• Mol file: 10544-63-5.mol

Synonyms:Ethyl but-2-enoate;2-Butenoic acid, ethyl ester;but-2-enoic acid ethyl ester;Crotonic acid ethyl ester;ethyl butenoate;Ethyl-2-Crotonate;DTXSID8065119;AKOS025243553;FT-0625771;FT-0626173;FT-0642600;FT-0686368

Chemical Property of 2-Butenoic acid, ethyl ester

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 6.87mmHg at 25°C
• Melting Point: 37.22°C (estimate)
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 137.999 °C at 760 mmHg
• Flash Point: 28.333 °C
• PSA: 26.30000
• Density: 0.916 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

Purity/Quality:

99% ^*data from raw suppliers

CrotonicAcidEthylEster ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C=CC
• Uses: Crotonic Acid Ethyl Ester, is an intermediate for the preparation of various pharmaceutical compounds. It can be used for the synthesis of (+)-trans-Trikentrin A.

Technology Process of 2-Butenoic acid, ethyl ester

There total 41 articles about 2-Butenoic acid, ethyl ester 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: 92.0%

(-)-(R)-Ethyl 3-(mesyloxy)butanoate (126434-58-0) → ethyl 3-hydroxybutyrate (5405-41-4) + ethyl crotonate (10544-63-5) + ethyl (S)-(+)-3-azidobutyrate (226910-85-6)

Guidance literature:

With sodium azide; In formamide; at 40 - 100 ℃; for 0.5 - 13h; Product distribution / selectivity;

Reference yield: 89.0%

ethyl 3-[(2-fluorobenzoyl)methylamino]butyrate (1285712-37-9) → ethyl crotonate (10544-63-5) + 2‐fluoro‐N‐methylbenzamide (52833-63-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1055/s-0030-1258302

Reference yield: 87.0%

methylmagnesium bromide (75-16-1) + propynoic acid ethyl ester (623-47-2) → ethyl crotonate (10544-63-5)

Guidance literature:

With chloro-trimethyl-silane; copper(I) iodide-lithium chloride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1002/ejoc.200400314

upstream raw materials:

1,1,1-Trichloro-3-bromobutane

sodium ethanolate

ethyl acetoacetate

(Z)-but-2-enoic acid

Downstream raw materials:

3-methyl-2-(3,4,5-trimethoxy-benzoyl)-glutaric acid diethyl ester

2-methyl-propane-1,1,3-tricarboxylic acid triethyl ester

3-methyl-4-nitrobutyric acid ethyl ester

2-methylbutanedioic acid

Refernces

• 1、 Kurcok, Piotr,Jedlinski, Zbigniew,Kowalczuk, Marek. "Reactions of β-Lactones with Potassium Alkoxides and Their Complexes with 18-Crown-6 in Aprotic Solvents". . p. 4219 - 4220. Retrieved 1993.
• 2、 Dong, Guangbin,Xu, Yan,Zhou, Xukai. "Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones". supporting information. p. 20042 - 20048. Retrieved 2021/12/03.
• 3、 -. "Method for synthesizing muscone by utilizing beta-monomethyl methylglutarate". Paragraph 0021; 0022. . Retrieved 2017/12/05.