59803-32-6

Basic information

• Product Name: Ethyl 3-(2-BroMophenyl)-2-cyanoacrylate
• Synonyms: Ethyl 3-(2-BroMophenyl)-2-cyanoacrylate
• CAS NO: 59803-32-6
• Molecular Formula: C₁₂H₁₀BrNO₂
• Molecular Weight: 280.1173
• Mol File: 59803-32-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 68.9-69.3 °C
• Boiling Point: 381°Cat760mmHg
• Flash Point: 184.2°C
• Appearance: /
• Density: 1.453g/cm³
• Vapor Pressure: 5.22E-06mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: Ethyl 3-(2-BroMophenyl)-2-cyanoacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-(2-BroMophenyl)-2-cyanoacrylate(59803-32-6)
• EPA Substance Registry System: Ethyl 3-(2-BroMophenyl)-2-cyanoacrylate(59803-32-6)

Safety Data

• Hazardous Substances Data: 59803-32-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H10BrNO2/c1-2-16-12(15)10(8-14)7-9-5-3-4-6-11(9)13/h3-7H,2H2,1H3/b10-7+

Upstream product

• 64-17-5 ethanol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 107-91-5 cyanoacetic acid amide 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 59803-41-7 3-(2-bromo-phenyl)-2-cyano-propionic acid ethyl ester 
• 1575816-39-5 ethyl 3-amino-1-(2-bromophenyl)-1H-benzo[f]chromene-2-carboxylate 
• 36926-83-7 ethyl 2-aminoquinoline-3-carboxylate 
• 1649438-43-6 triethyl 6-amino-4-(2-bromophenyl)-1-(4-bromophenyl)-1,4-dihydropyridine-2,3,5-tricarboxylate 
• 1372800-93-5 (1S,2R,3R)-triethyl 2'-bromo-2-cyano-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2,3,4-tricarboxylate 

Relevant articles and documents

l-Lysine Functionalized Polyacrylonitrile Fiber: A Green and Efficient Catalyst for Knoevenagel Condensation in Water

Abstract: The l-lysine functionalized polyacrylonitrile fiber (PANLF) was prepared by grafting the l-lysine into a commercially available polyacrylonitrile fiber and showed highly catalytic activity for Knoevenagel condensation reaction. With low temperature (45?°C) and short reaction time (1?h), the fiber catalyst was well applicable to Knoevenagel condensation of a wide range of aldehydes and the yields could reach up to 99%. Interestingly, only in water could the reaction take place smoothly (with a yield of 88%) and a polar micro-environment promoted reaction process had been proposed to explain this phenomenon. Besides, the fiber catalyst has advantages of easy preparation, high functional degree, strong mechanical strength and thermal stability, etc. And it can be reused at least 5 times without further treatment and performed well in scaled-up experiment (amplified 50 times) and flow chemistry experiment (no loss of catalytic activity after 48?h), which indicates its potential application in industry application. Graphical Abstract: [Figure not available: see fulltext.].

Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization

A novel regioselective synthesis of 2-aminoquinolines and 2-arylquinoline-3-carbonitriles is described via copper-mediated tandem reaction. Formation of substituted quinolines involves Knoevenagel condensation of ortho-bromobenzaldehyde with active methylene nitriles followed by copper-catalyzed reductive amination and intramolecular cyclization.

Applications of caged-designed proton sponges in base-catalyzed transformations Dedicated to Professor Milan Kratochvíl for his 90th birthday anniversary.

Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (DMAN). The basicity (in MeCN) of our chosen DTD (pKBH+=21.7±0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pKBH+=18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (～130°) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions.