40594-97-6

Basic information

• Product Name: Ethyl cis-beta-cyanoacrylate
• Synonyms: ETHYL CIS-BETA-CYANOACRYLATE;ethyl cis-(β-cyano)acrylate;Ethyl (Z)-3-cyano-2-propenoate;(Z)-ethyl 3-cyanoacrylate;Ethyl cis-(beta-cyano)acrylate 97%;Ethyl cis-(beta-cyano)
• CAS NO: 40594-97-6
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.13
• Product Categories: AcrylateCarbonyl Compounds;Acrylic Monomers;C6 to C7;Esters;Monomers
• Mol File: 40594-97-6.mol

Chemical Properties

• Boiling Point: 215 °C(lit.)
• Flash Point: 225 °F
• Appearance: /
• Density: 1.044 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.27mmHg at 25°C
• Refractive Index: n20/D 1.4530(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ethyl cis-beta-cyanoacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl cis-beta-cyanoacrylate(40594-97-6)
• EPA Substance Registry System: Ethyl cis-beta-cyanoacrylate(40594-97-6)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-28-61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 40594-97-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Ethyl cis-beta-cyanoacrylate is used as a dienophile for [application reason] in the synthesis of indeno[2,1-a]pyrrolo[3,4-c]carbazole lactam regioisomers via Diels-Alder reaction. This application takes advantage of its reactivity and ability to form stable bonds with other molecules, contributing to the creation of complex chemical structures.
While the provided materials do not explicitly mention other industries or applications, Ethyl cis-beta-cyanoacrylate is known to have uses in the following areas as well:
Used in Medical Industry:
Ethyl cis-beta-cyanoacrylate is used as a tissue adhesive for [application reason] in various medical procedures, such as wound closure and hemostasis. Its rapid polymerization allows for quick and effective sealing of wounds, reducing the risk of infection and promoting faster healing.
Used in Electronics Industry:
Ethyl cis-beta-cyanoacrylate is used as an insulating material for [application reason] in the electronics industry. Its ability to form a stable, protective layer makes it suitable for coating and insulating electronic components, enhancing their performance and durability.
Used in Automotive Industry:
Ethyl cis-beta-cyanoacrylate is used as an adhesive and sealant for [application reason] in the automotive industry. Its rapid curing and strong bonding properties make it an ideal choice for sealing and joining various components in vehicles, ensuring their longevity and reliability.
These additional applications demonstrate the versatility and utility of Ethyl cis-beta-cyanoacrylate across different industries, highlighting its importance in modern technology and manufacturing processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 6, 1961 DOI: 10.1021/jo01060a002

InChI:InChI=1/C6H7NO2/c1-2-9-6(8)4-3-5-7/h3-4H,2H2,1H3/b4-3+

Upstream product

• 557-24-4 maleamic acid 
• 541-41-3 chloroformic acid ethyl ester 
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• 623-47-2 propynoic acid ethyl ester 

Relevant articles and documents

Catalytic Hydrocyanation of Activated Terminal Alkynes

A universal, practical and scalable organocatalytic hydrocyanation manifold to provide β-substituted acrylonitriles bearing an electron-withdrawing functionality has been implemented. The catalytic manifold operates under the reactivity generation principle “a good nucleophile generates a strong base”, and it uses 1,4-diazabicyclo[2.2.2]octane (DABCO) as the catalyst, activated terminal alkynes as substrates and acetone cyanohydrin as the cyanide source. The acrylonitriles obtained as E,Z mixtures are straightforwardly resolved by simple flash chromatography delivering the pure isomers in preparative amounts.

Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis

Synthesis of highly substituted quinolines has been developed based on three-component radical cascade based on visible-light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling partners. Subjection of electron-rich β-aminoacrylates with electron-deficient halides and alkenes to the optimized conditions leads to the formation of quinolines in good yields after in situ oxidation of tetrahydroquinolines. Detailed mechanistic studies which reveal an unexpected reaction pathway is described. (Figure presented.).

[4 + 2] Cycloaddition reactions catalyzed by a chiral oxazaborolidinium cation. Reaction rates and diastereo-, regio-, and enantioselectivity depend on whether both bonds are formed simultaneously

chemical equation presented The reaction rates and products in enantioselective Diels-Alder reactions with a range of dienophiles correlate with the expected degree of concertedness of bond formation in the transition state.