33534-88-2

Upstream product

• 624-31-7 4-tolyl iodide 
• 109-77-3 malononitrile 
• 874-60-2 4-methyl-benzoyl chloride 
• 106-43-4 para-chlorotoluene 
• 131211-27-3 di-1-adamantylphosphine 
• 4341-85-9 malonitrile 
• 30698-52-3 2-cyano-2-(p-tolyl) acetamide 
• 30698-31-8 methyl 2-cyano-2-(p-tolyl) acetate 
• 106-38-7 para-bromotoluene 
• 865-48-5 sodium t-butanolate 
• 86866-05-9 2-p-Tolyl-2-trimethylsilanyloxy-malononitrile 
• 91880-02-3 (1,2,3-trimethylcyclopropenyl)(p-methylphenyl)malononitrile 
• 99779-70-1 2-Chloro-2-p-tolyl-malononitrile 
• 2947-61-7 (4-methylphenyl)acetonitrile 

Downstream Products

• 14271-73-9 4-methylbenzoyl cyanide 
• 91880-02-3 (1,2,3-trimethylcyclopropenyl)(p-methylphenyl)malononitrile 
• 1393345-90-8 4-(p-tolyl)-1H-pyrazole-3,5-diamine 
• 37449-71-1 4-methyl-α,α-dicyanobenzyl radical 

Relevant academic research and scientific papers

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.

Effect of Substituents on the Bond Strength of Air-Stable Dicyanomethyl Radical Thermochromes

A series of substituted aryl dicyanomethyl radicals were synthesized, and the bonding thermodynamic parameters for self-dimerization were determined from van't Hoff plots obtained from variable-temperature electron paramagnetic resonance and ultraviolet-v

Synthesis of substituted isoquinolines via Pd-catalyzed cross-coupling approaches

Palladium complexes incorporating ligands based on a 1,3,5,7-tetramethyl-2, 4,8-trioxa-6-phosphaadamantanyl scaffold were used to catalyze the arylation of ethyl cyanoacetate, malononitrile, and various ketones. The products from these reactions can be el

A convenient protocol for the synthesis of hindered aryl malononitriles

A technically feasible method has been developed for the synthesis of variety of aryl malononitriles in high yields (70-95%) using the palladium-catalyzed coupling reaction of malononitrile with aryl bromides and chlorides, respectively. The influence a s

PROCESS FOR THE PREPARATION OF PHENYLMALONIC ACID DINITRILES

Phenylmalonic acid dinitriles are prepared by reaction of, for example, phenyl Kalides with malonic acid dinitrile in the presence of palladium catalysts and bases.

A highly efficient catalytic system for cross-coupling of aryl chlorides and bromides with malononitrile anion by palladium carbene complexes

Six imidazolium chlorides (1-6) as precursors of 1,3-diaryl substituted N-heterocyclic carbene ligands were synthesized and evaluated in palladium-catalyzed cross-coupling reactions of aryl chlorides and bromides with malononitrile in the presence of NaH.

A convenient and efficient palladium-catalyzed system for cross-coupling of aryl bromides with active methylene compounds

A simply catalytic system containing palladium-phosphine complex, generated in situ from PdCl2/tert-phosphino ligand in pyridine, has been systematically studied in the cross-coupling of bromobenzene with malononitrile or ethyl cyanoacetate anion. The effect of molar ratio of phosphine ligand to PdCl2 on the activity of the coupling was also discussed. It is found that the catalytic system has highly catalytic activity to produce aryl malononitriles and cyanoacetates in considerable yields (67-90%) when the substituted aryl bromides were used as substrates.

Coupling of nucleophiles, vinyl compounds or CO with water, alcohols or amines to organic compounds

Process for the coupling of a) nucleophiles selected from the group alcohols, thioles, amines, metallised hydrocarbons, CH-acidic compounds and metal cyanides, or of b) carbon monoxide mixed with water, alcohols, ammonia, primary or secondary amines, to organic compounds selected from the group of leaving-group-containing aromatics, hetero-aromatics with a C-bonded leaving group, aromatic or hetero-aromatic methyl compounds with a leaving group bonded to the methyl group, ethylenically unsaturated organic compounds with a C-bonded leaving group, or organic allyl compounds with a leaving group in allyl position, or c) vinyl compounds with leaving-group-containing aromatics, whilst cleaving the leaving group in the presence of Pd complexes with monophospholine ligands as the catalyst, whereby variants b) and c) are carried out in the presence of an inorganic base or organic nitrogen base, the process being characterised in that the Pd complex contains secondary monophosphines with aliphatic, branched or cyclic substituents as ligands.

Anomalous Reaction of Arylmalononitriles with Nitric Acid. Para-Directing Nature of Dicyanomethyl Group and a Through-Ring Nitro/aci-Nitro Tautomerism of 4-Nitrophenylmalononitrile

Phenylmalononitrile reacts with nitric acid in dichloromethane at room temperature to afford 1,2-bis(4-nitrophenyl)-1,1,2,2-tetracyanoethane as an initial product, which readily suffers oxidative cleavage to give 4-nitrobenzoyl cyanide.Contrary to common

Termodynamics and Kinetics of Carbon-Carbon Bond Formation and Heterolysis Through Reactions of Carbocations with Carbanions in Solution

Rate data are presented for the heterolysis of carbon-carbon bonds and their formation through coordination of resonance-stabilized carbocations and carbanions in acetonitrile solution at 25 deg C.These rates were determined by NMR line broadening and by the T jump technique (in a solution containing 0.48 M supporting electrolyte).Preliminary results are given for a "master equation" to predict some heterolysis energies in solution as a complement to Benson's method for homolysis energies.The results provide for the first time an opportunity to compare the effects of structure variation on the kinetic and thermodynamic properties for such an ostensibly simple reaction in solution.All evidence so far accumulated indicates that these reactions are dominated by ion-solvation factors so that they have little bearing on the gas-phase heterolysis energies.Ionic strength effects and substituent variation suggest that charge development is about half developed at the transition state, but we argue that this cannot be translated simply into pictures of transition-state structure.The results provide a flagrant reversal of the frequently invoked "reactivity selectivity principle" since the most reactive cation is also most selective.On the basis of these results and many others which have appeared recently it may be appropriate to discard the reactivity selectivity principle as a useful principle for either prediction or interpretation.