40595-04-8

Basic information

• Product Name: ethyl (Z)-3-cyanobut-2-enoate
• Synonyms: ethyl (Z)-3-cyanobut-2-enoate
• CAS NO: 40595-04-8
• Molecular Formula: C7H9NO2
• Molecular Weight: 0
• Mol File: 40595-04-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 220.8°Cat760mmHg
• Flash Point: 93.8°C
• Appearance: /
• Density: 1.035g/cm³
• Vapor Pressure: 0.111mmHg at 25°C
• Refractive Index: 1.449
• CAS DataBase Reference: ethyl (Z)-3-cyanobut-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (Z)-3-cyanobut-2-enoate(40595-04-8)
• EPA Substance Registry System: ethyl (Z)-3-cyanobut-2-enoate(40595-04-8)

Safety Data

• Hazardous Substances Data: 40595-04-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H9NO2/c1-3-10-7(9)4-6(2)5-8/h4H,3H2,1-2H3/b6-4-

Upstream product

• 7719-09-7 thionyl chloride 
• 6330-37-6 ethyl 3-cyano-3-hydroxybutanoate 
• 557-21-1 zinc(II) cyanide 
• 122135-84-6 ethyl (Z)-3-(((trifluoromethyl)sulfonyl)oxy)but-2-enoate 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 22584-00-5 rac-ethyl 3-cyanobutanoate 

Relevant articles and documents

Chemoenzymatic asymmetric synthesis of pregabalin precursors via asymmetric bioreduction of β-cyanoacrylate esters using ene-reductases

The asymmetric bioreduction of a library of β-cyanoacrylate esters using ene-reductases was studied with the aim to provide a biocatalytic route to precursors for GABA analogues, such as pregabalin. The stereochemical outcome could be controlled by substrate-engineering through size-variation of the ester moiety and by employing stereochemically pure (E)- or (Z)-isomers, which allowed to access both enantiomers of each product in up to quantitative conversion in enantiomerically pure form. In addition, stereoselectivities and conversions could be improved by mutant variants of OPR1, and the utility of the system was demonstrated by preparative-scale applications.