759-51-3

Basic information

• Product Name: ethyl 2-cyano-3-methylpent-2-ene-1-oate
• Synonyms: ethyl 2-cyano-3-methylpent-2-ene-1-oate;2-Cyano-3-methyl-2-pentenoic acid ethyl ester;2-Pentenoic acid, 2-cyano-3-methyl-, ethyl ester;Ai3-04908;Einecs 212-069-6;(E/Z)-2-Cyano-3-methyl-2-pentenoic Acid Ethyl Ester;(E/Z)-Ethyl 2-Cyano-3-Methyl-2-pentenoate;NSC 67978
• CAS NO: 759-51-3
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.20502
• EINECS: 212-069-6
• Product Categories: Intermediates
• Mol File: 759-51-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 256.3°C at 760 mmHg
• Flash Point: 113.8°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.0155mmHg at 25°C
• Refractive Index: 1.452
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: ethyl 2-cyano-3-methylpent-2-ene-1-oate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-cyano-3-methylpent-2-ene-1-oate(759-51-3)
• EPA Substance Registry System: ethyl 2-cyano-3-methylpent-2-ene-1-oate(759-51-3)

Safety Data

• Hazardous Substances Data: 759-51-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

Intermediate in the preparation of Ethosuximide.

InChI:InChI=1/C9H13NO2/c1-4-7(3)8(6-10)9(11)12-5-2/h4-5H2,1-3H3/b8-7+

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 78-93-3 butanone 
• 125256-49-7 C₇H₁₆N₄ 
• 25468-53-5 ethyl (2Z)-2-cyano-3-ethoxypent-2-enoate 

Downstream Products

• 7309-45-7 ethyl 2-cyano-3-methylvalerate 
• 70289-04-2 3-benzyl-2-cyano-3-methyl-valeric acid ethyl ester 
• 372-09-8 cyanoacetic acid 
• 141-82-2 malonic acid 
• 107456-80-4 2,3-Dicyan-3-methyl-2-(phenylmethyl)pentansaeure-ethylester 
• 21101-83-7 2-cyano-3-methyl-3-phenyl-valeric acid ethyl ester 
• 70289-02-0 3-Methyl-3-ethyl-2-cyan-hexansaeure-ethylester 
• 24543-23-5 3-ethyl-1,2,2-tricyano-3-methyl-cyclopropanecarboxylic acid ethyl ester 

Relevant articles and documents

Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives

In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substituted anilines has been improved using the microwave irradiation. Significantly higher yields compared to conventional condensation have been observed. The preliminary biological results indicated that some of the synthesized compounds showed promising in vitro antifungal activities towards several test fungi. 1-(4-Bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8) exhibited significant in vitro inhibitory activities against broad spectra of fungus, and on the basis of obtained data, the investigated bromo derivative has to be observed as novel potential fungicide. The density functional theory (DFT) calculations have been performed in order to study the structure-activity relationship (SAR) of the investigated molecules. In order to prediction of the chemical activity of the molecule, the molecular electrostatic potential (MEP) map was analyzed for the optimized geometry of 1-phenyl-3-ethyl-3-methylpyrrolidine-2,5-dione (4) and 1-(4-bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8).

Steric effects in high pressure Knoevenagel reactions

The pressure effect in Knoevenagel condensations involving ketones and ethyl cyanoacetate is studied. The reactions are diversely affected. For cyclic ketones there is a small effect on the reaction yield. However, in the case of acyclic ketones, the sensitivity of the reaction to pressure increases with increasing steric congestion of the ketone. Such a result highlights the synthetic utility of high pressure for the preparation of hindered functionalized alkenes.

Transition metal polyhydrides-catalyzed addition of activated nitriles to aldehydes and ketones via Knoevenagel condensation

Transition metal polyhydrides and dihydrogen complexes catalyze Knoevenagel addition of cyanoacetate to aldehydes and ketones under neutral and mild conditions, the adducts undergo dehydration to give substituted (E)-2-cyano-α,β-unsaturated esters exclusively.