58243-08-6

Usage

Chemical Properties

clear light yellow liquid

InChI:InChI=1/C5H7NO/c1-2-7-5-3-4-6/h3,5H,2H2,1H3/b5-3+

Upstream product

• 64-17-5 ethanol 
• 871-29-4 trans-β-chloroacrylonitrile 
• 23521-49-5 (Z)-1-bromo-2-ethoxyethene 
• 151-50-8 potassium cyanide 
• 2032-34-0 3,3-bis(ethyloxy)propanenitrile 

Downstream Products

• 137378-90-6 cis-4'-Ethoxy-4-oxospiro(cyclohexa-2,5-diene-1,2'-oxetane)-3'-carbonitrile 
• 137378-90-6 trans-4'-Ethoxy-4-oxospiro(cyclohexa-2,5-diene-1,2'-oxetane)-3'-carbonitrile 
• 403719-53-9 (1Z,4E)-2-cyano-1-ethoxy-6,6-dimethyl-4-(phenylthio)hepta-1,4-dien-3-ol 
• 403719-73-3 (1Z,4Z,6Z)-2,6-dicyano-1-ethoxy-8,8-dimethyl-4-(phenylthio)nona-1,4,6-trien-3-ol 
• 156-81-0 2,4-diaminopyrimidine 
• 23220-67-9 (E)-β-morpholino acrylonitrile 
• 71-30-7 Cytosine 
• 89977-46-8 1-(2-pyridinyl)-1H-pyrazol-5-ylamine 

Relevant academic research and scientific papers

Process for the preparation of 3-alkoxyacrylonitrile

The present invention provides a process, which includes: preparing 3-alkoxyacrylonitrile from 3,3-dialkoxypropionitrile by catalytically eliminating alcohol from 3,3-dialkoxypropionitrile in the presence of at least one aromatic sulfonic acid catalyst and at least one high-boiling solvent. Another embodiment of the invention provides a method of producing a pharmaceutical compound, which includes the above-described process. Another embodiment of the invention provides a method of producing a cosmetic product, which includes the above-described process.

The Cyanation of Vinyl Halides with Alkali Cyanides Catalyzed by Nickel(0)-Phosphine Complexes Generated In Situ: Synthetic and Stereochemical Aspects

The cyanation of β-bromostyrenes catalyzed by Ni(PPh3)n, which was generated in situ from NiBr2(PPh3)2-Zn-PPh3 (Ni:Zn:P=1:3:2 molar ratio), was at first examined with various MCN (M=K, Na)-dipolar aprotic solvent systems by several procedures.The presence of excess cyanide ion inhibited the reaction.However, when the KCN-DMF system with some intermediate cyanide solubility was used, the nitriles were obtained in high yields and high stereoselectivity at 50 deg C by almost all of the procedures attempted.On the contrary, the KCN-HMPA and KCN-MeCN systems with cyanide solubilities accelerated the coupling of the halides to inhibit the cyanation, and in general the NaCN-DMF and NaCN-HMPA systems with high cyanide solubilities needed to reduce Ni(II) before adding MCN in order to make the catalytic reaction start.Vinyl halides such as 1- and 2-halo (Cl, Br)-1-alkenes, 2-bromo-2-butenes, 3-bromo-3-hexenes, and 1-chlorocyclohexene were also cyanated using suitable procedures and MCN-solvent systems to give the corresponding nitriles in high yields and fair-to-good stereoselectivities.However, with (Z)-2-ethoxy-1-bromoethene the (E)-nitrile, though its selectivity markedly varied with the reaction temperature, was obtained as the main product.The cyanation of ethyl (Z)-β-bromoacrylate and ethyl α-bromoacrylate was unsuccessful due to polymerization.