1202-47-7

Upstream product

• 5593-65-7 2-cyano-4-phenylbutanamide 
• 103-63-9 1-phenyl-2-bromoethane 
• 109-77-3 malononitrile 
• 93031-12-0 ethyl phenethylcyanoacetate 
• 3695-83-8 2-(2-phenylethylidene) malononitrile 
• 100-42-5 styrene 
• 6904-17-2 1,1-dicyano-2-phenylcyclopropane 
• 122-78-1 phenylacetaldehyde 
• 100-52-7 benzaldehyde 

Downstream Products

• 1447-17-2 3-Phenyl-1,1,1-tricyan-propan 
• 2046-18-6 4-phenylbutyronitrile 
• 606148-72-5 2-(2-phenylethyl)-2-ethylmalononitrile 
• 606148-73-6 2-(2-phenylethyl)-2-allylmalononitrile 
• 152902-61-9 3,5-diamino-4-phenethylpyrazole 

Relevant academic research and scientific papers

Radical trifunctionalization of hexenenitrile via remote cyano migration

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alken

Solvent-free preparation method of di-substituted malononitrile derivative

The invention relates to a solvent-free preparation method of a di-substituted malononitrile derivative. The solvent-free preparation method comprises: 1, adding malononitrile, aromatic aldehyde and dihydropyridine ester to a reaction test tube according

Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides

A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.

Tris(trimethylsilyl)silane-mediated reductive decyanation and cyano transfer reactions of malononitriles

Reductive decyanation reactions of malononitriles were achieved with tris(trimethylsilyl)silane as a radical mediator. The reaction proceeds via a radical chain mechanism involving a silyl radical addition to the malononitrile to form an imidoyl radical followed by α-cleavage to give a silyl isocyanide and an α-cyano radical. The reaction of a 3-butenyl-substituted malononitrile afforded a decyano/cyanosilylation product in good yield through 1,4-cyano transfer.

Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System

A convenient low-cost method for regioselective ring-opening of donor-acceptor cyclopropanes with the Zn-AcOH reductive system was developed. The general character of the method was displayed via efficient reduction of a representative series of 2-(het)arylcyclopropane-1,1-diesters as well as donor-acceptor cyclopropanes with other types of electron-withdrawing activating groups. This method opens a rapid access to γ-substituted propyl-1,1-diesters, ketoesters, cyanoesters, cyanoamides, dinitriles, etc., many of which are not readily accessible with alternative methods. The utility of the synthesized compounds was demonstrated by transforming them into valuable acyclic and cyclic compounds (including pharmacologically relevant carbazoles, δ-lactams, and oxindole derivatives).

Photochemical monoalkylation of propanedinitrile by electron-rich alkenes

(Chemical Equation Presented) The synthesis of monoalkylated propanedinitriles was achieved upon photoirradiation of MeCN/H2O solutions containing propanedinitrile (1; malononitrile) and electron-rich alkenes in the presence of lithium carbonate and a catalytic amount of 9-cyanophenanthrene or redox-type photosensitizers (electron-mediating photosensitizers), through regioselective anti-Markovnikov photochemical polar addition of 1 into electronrich alkenes. With 2,5-dimethyl-2,4-hexadiene (2g) as an electron-rich alkene, propanedinitrile-incorporated dimer 4g was obtained.

Superacid-catalyzed intramolecular cyclization reaction of arylcyanopropionate: Geminal substitution effect on superelectrophilicity

(Chemical Equation Presented) We present superacid-catalyzed intramolecular cyclization reactions of arylcyanopropionates to give cyclized five- and six-membered β-enamino esters in moderate to high yields. Known intramolecular ring-closing reactions of protonated nitrile to aromatic carbon atom are limited to the 6-membered case. Interestingly, a significant synergistic increase of reactivity of the cyano functionality was observed, and the cyano nitrogen atom was converted into an amino group, when an ester group was present in a geminal arrangement. Deuterium exchange experiments excluded the involvement of deprotonation of the α-proton in the cyclization process. The acidity dependence of the cyclization reactions and 13C NMR studies of a model compound, methyl cyanoacetate, in various acidic media were consistent with the involvement of the O,N-diprotonated dication of methyl cyanoacetate, a distonic dication, in strong acid, and this is considered to be the de facto electrophile in the present cyclization reaction of arylcyanopropionates.

Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497

A new application of nitrile-converting enzymes in the synthesis of optically active α,α-disubstituted-α-cyanoacetamides from α,α-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral α,α-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods.

Synthesis of 4-Alkylpyrazoles from 3,5-Diaminopyrazoles

The possibility of preparing 4-alkylpyrazole from malononitrile (through C-alkyl malononitriles and 3,5-diamino-4-alkylpyrazoles) has been explored.Although some difficulties arise in the double-deamination step, the method has allowed the synthesis of 4-benzyl-and 4-phenyl-pyrazoles.New 3-halogenopyrazoles have also been prepared.The synthesis of 3,5-diamino-4-iodopyrazole is reported.This elusive compound has a 13C NMR spectrum in which an aromatic carbon (C-4) appears at δ 29,53.