868-04-2

Basic information

• Product Name: Ethyl2-cyano-3-ethyl-2-pentenoate
• Synonyms: Ethyl2-cyano-3-ethyl-2-pentenoate;Ethyl 2-Cyano-3,3-diethylacrylate;2-CYANO-3-ETHYL-PENT-2-ENOIC ACID ETHYL ESTER;ETHYL 2-CYANO-3-ETHYLPENT-2-ENOATE
• CAS NO: 868-04-2
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.2316
• Mol File: 868-04-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 273.8°C at 760 mmHg
• Flash Point: 123.7°C
• Appearance: /
• Density: 0.986g/cm³
• Vapor Pressure: 0.00562mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: Ethyl2-cyano-3-ethyl-2-pentenoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl2-cyano-3-ethyl-2-pentenoate(868-04-2)
• EPA Substance Registry System: Ethyl2-cyano-3-ethyl-2-pentenoate(868-04-2)

Safety Data

• Hazardous Substances Data: 868-04-2(Hazardous Substances Data)

Usage

Uses

Ethyl 2-Cyano-3,3-diethylacrylate is a product of Knoevenagel condensation. Ethyl 2-Cyano-3,3-diethylacrylate can be synthesized to verify effectiveness of the silica catalysts for Knoevenagel condensation.

InChI:InChI=1/C10H15NO2/c1-4-8(5-2)9(7-11)10(12)13-6-3/h4-6H2,1-3H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 96-22-0 pentan-3-one 

Downstream Products

• 5692-97-7 2,2-diethylsuccinic acid 
• 6637-50-9 3,3-Diethylpentanoic Acid 
• 80721-13-7 4,4-diethyl-2,6-dioxo-piperidine-3,5-dicarbonitrile 
• 53608-83-6 3-ethyl-2-cyano-2-methyl-pent-3-enoic acid ethyl ester 
• 28456-66-8 3-Ethyl-2-cyan-pentansaeure-ethylester 
• 4160-95-6 3,3-diethylpentanedioic acid 
• 24543-21-3 3,3-Diaethyl-1,2,2-tricyan-cyclopropan-1-carbonsaeure-aethylester 

Relevant articles and documents

Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids

Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.

Ionic liquid as catalyst and reaction medium - A simple, efficient and green procedure for Knoevenagel condensation of aliphatic and aromatic carbonyl compounds using a task-specific basic ionic liquid

The basic ionic liquid 1-butyl-3-methylimidazolium hydroxide, [bmIm]OH, efficiently catalyzes Knoevenagel condensation without requirement of any organic solvent. A wide range of aliphatic and aromatic aldehydes and ketones easily undergo condensations with diethyl malonate, malononitrile, ethyl cyanoacetate, malonic acid and ethyl acetoacetate. The reactions proceed at room temperature and are very fast (10-30 min). However, the most significant feature of this methodology is the condensation of aliphatic aldehyde with diethyl malonate, which is not very easy to achieve by conventional reagents, and was not addressed adequately in literature providing a general and convenient procedure. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Silica-supported imines as mild, efficient base catalysts

Imine grafted silicas are found to be mild and effective base catalysts for Knoevenagel and Michael reactions.