57746-44-8

Usage

Uses

Used in Organic Synthesis:
(2,4-dinitrophenyl)acetonitrile is used as a reagent in organic synthesis for the synthesis of various compounds. Its unique chemical properties make it a valuable component in the creation of a range of products.
Used as a Precursor:
In the chemical industry, (2,4-dinitrophenyl)acetonitrile serves as a precursor for the preparation of other chemical compounds. Its role in the synthesis of derivatives is crucial for developing new materials and substances.
Safety Considerations:
It is important to handle (2,4-dinitrophenyl)acetonitrile with care due to its toxic nature, which can cause skin and eye irritation. Proper safety guidelines should be followed during its handling and storage to prevent accidents and exposure.

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 61540-35-0 S-(Dimethylthiocarbamoyl)thioglycolonitrile 
• 3598-14-9 phenoxyacetonitrile 
• 19051-22-0 α-cyano-2,4-dinitrostilbene 
• 107-14-2 chloroacetonitrile 
• 121-14-2 2,4-dinitrotoluene 
• 61293-29-6 (E)-2-(2,4-dinitrophenyl)-N,N-dimethyl-1-ethenamine 
• 75-05-8 acetonitrile 

Downstream Products

• 6746-78-7 α-(Diphenyl-cyclopropenyliden)-2,4-dinitro-phenylacetonitril 
• 19051-22-0 α-cyano-2,4-dinitrostilbene 

Relevant academic research and scientific papers

Development of Green/Red-Absorbing Chromophores Based on a Coumarin Scaffold That Are Useful as Caging Groups

We report the design, synthesis, and spectroscopic characterization of a series of push-pull chromophores based on a novel coumarin scaffold in which the carbonyl of the lactone function of the original coumarin dyes has been replaced by the cyano(4-nitro

An efficient one-step method for the conversion of β-(dimethylamino) styrenes into arylacetonitriles

A new simple and efficient one-step method for the preparation of arylacetonitriles by reaction of β-(dimethylamino)styrenes with hydroxylamine hydrochloride in formic acid solution is described. Georg Thieme Verlag Stuttgart.

Kinetics of proton transfer from 2-nitro-4-X-phenylacetonitriles to piperidine and morpholine in aqueous Me2SO. Solvent and substituent effects on intrinsic rate constants. Transition state imbalances

Rate constants (k1(B)) for the deprotonation of 2-nitro-4-X-phenylacetonitrile, 2-X (X = NO2, SO2CH3, CN, CF3, Br, and Cl) by piperidine and morpholine and for the reverse reaction (k-1(BH)) have been determined in 90% Me2SO- 10% water, 50% Me2SO-50% water, and water (X = NO2, SO2CH3, CN only). Bronsted β(B) values (dlog k1(B)/dpK(a)(BH)), Bronsted α(CH) values (dlog k1(B)/dlog K(a)(CH)), and intrinsic rate constants (log k(o) = log(k1/q) for pK(a)(BH)-p K(a)(CH) + log(p/q) = 0) were calculated from these data. α(CH) is smaller than β(B), implying an imbalance wnich is consistent with a transition state in which delocalization of the negative charge into the 2-nitrophenyl moiety lags behind proton transfer. A consequence of this imbalance is that the intrinsic rate constant decreases with increasing electron withdrawing strength of X. For π-acceptor substituents (NO2, SO2CH3, CN) there is a further decrease in k(o) due to a lag in the delocalization of the charge into X. The intrinsic rate constants depend very little on the Me2SO content of the solvent which is shown to be the result of compensation of mainly two competing factors. One is the stabilization of the polarizable transition state by the polarizable Me2SO which increases k(o); the other is attributed to a lag in the solvation of the developing carbanion behind proton transfer at the transition state which leads to a decrease in k(o).

Direct coupling of carbon nucleophiles with m-dinitrobenzene: A novel fluoride promoted nucleophilic aromatic photosubstitution for hydrogen

Useful yields are achieved in the C-arylation of ketones, nitriles and esters through direct hydrogen nucleophilic aromatic photosubstitution of m-dinitrobenzene, promoted by fluoride anion.

Specific ortho-Cyanomethylation of Nitroarenes via the Vicarious Nucleophilic Substitution of Hydrogen

The vicarious nucleophilic substitution of hydrogen in nitroarenes with acetonitrile derivatives XCH2CN in t-BuOK/THF base/solvent system proceeds exclusively ortho to the nitro group.Strong influence of substituents Z in 3-Z-nitrobenzene derivatives on the orientation has been observed.

Nucleophilic Addition to Olefins. 10. Kinetics of Cleavage of the Piperidine and Morpholine Adducts of α-Cyano-4-nitrostilbene and α-Cyano-2,4-dinitrostilbene

Rates of cleavage of the anionic piperidine and morpholine adducts (T-) of α-cyano-4-nitrostilbene (1-NO2) and α-cyano-2,4-dinitrostilbene (1-(NO2)2) into PhCH=+NR2 and 2-X-4-nitrophenylacetonitrile anion were determined.For the adducts of 1-(NO2)2 there is a change from rate-limiting carbon protonation (to form T0) at low amine concentrations to rate-limiting cleavage of T0 into products at high concentrations.For the adducts of 1-NO2 cleavage is rate limiting throughout.Compared to the protonation of the anion of (2,4-dinitrophenyl)acetonitrile (2-(NO2)2), protonation of T- derived from 1-(NO2)2 is slightly enhanced when the acid is water, strongly reduced when the acid is morpholinium or piperidinium ion (R2NH2+), and strongly enhanced with H3O+.The slightly enhanced rate of the water reaction is attributed to an enhanced pKa0 of the adduct, the strongly depressed rate for the R2NH2+ reactions to a steric effect.The enhanced rate with H3O1+ is ascribed either to an intramolecular pathway via the nitrogen-protonated adduct (T+/-) or to a stabilization, by the adjacent amine moiety, of the transition state for protonation by H3O+.Problems with either interpretation exist, though, and are discussed.Even after taking into account the different leaving group basicities, the cleavage of T0 derived from 1-NO2 is much slower than that of the previously studied T0 derived from benzylidenemalononitrile, indicating a higher intrinsic barrier for the departure of the more delocalized (4-nitrophenyl)acetonitrile anion compared to -CH(CN)2.This is consistent with similar patterns observed with other carbanion-forming reactions such as deprotonations of C-H acids and nucleophilic additions to olefins.If one allows for a steric enhancement of the cleavage of T0 derived from 1-(NO2)2, it appears that the intrinsic barrier for departure of 2-(NO2)2- is also higher than that for the somewhat less delocalized (4-nitrophenyl)acetonitrile anion.

RATES OF DEPROTONATION OF (4-NITROPHENYL)ACETONITRILE AND (2-4-DINITROPHENYL)ACETONITRILE IN 50% Me2SO--50% WATER.

Rates of reversible deprotonation of (2,4-dinitrophenyl)acetonitrile (2-(NO//2)//2) by OH** minus , water, piperidine, morpholine, cacodylate, acetate, formate, and chloroacetate ion and of (4-nitrophenyl)acetonitrile (2-NO//2) by OH** minus , piperidine, morpholine, n-butylamine, and 2-methoxyethylamine in 50% Me//2SO-50% water at 20 degree C are reported. The intrinsic rate constant (in the Marcus sense) for the dinitro derivative is about 10-fold lower than that for the mononitro compound. This is consistent with the stronger charge delocalization in the anion of the dinitro compound, which leads to greater structural/electronic/solvational reorganization during the reaction. Bronsted beta //B values (variation of base) for the deprotonation by piperidine and morpholine are 0. 50 for 2-(NO//2)//2 and 0. 74 for 2-NO//2, respectively. Bronsted alpha //C//H values (variation of C-H acid) are 0. 47 for deprotonation by morpholine and 0. 35 for deprotonation by piperidine.