2461-86-1

Upstream product

• 99-35-4 1,3,5-trinitrobenzene 
• 67-64-1 acetone 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 219654-05-4 C₉H₆N₃O₇^(1-) 
• 118-75-2 chloranil 
• 15225-54-4 tetramethylammonium tetrabutylborate 

Downstream Products

• 141031-73-4 1-methyl-2-picrylvinyl benzoate 
• 219654-05-4 C₉H₆N₃O₇^(1-) 

Relevant academic research and scientific papers

Alkylation of nitroaromatics with tetraalkylborate ion via electrochemical oxidation

Aromatic nucleophilic substitution reaction (SNAr) is one of the most thoroughly studied reactions. Alkylation of nitroaromatics with Grignard reagents via chemical oxidation of the σH-complexes is the most general method to introduc

Role of association of Yanovskii anionic σ adducts in their oxidation with quinones

In oxidation of 1,3-dinitro- and 1,3,5-trinitrobenzene acetonate σ adducts (Yanovskii complexes) with sodium, potassium, and tetrabutylammonium cations in acetonitrile and tetrahydrofuran (290-313 K), ion pairs are less reactive than free ions, which is e

Electrochemical synthesis of nitroaromatic ketones

Nitroaromatic ketones are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Carbanions of various ketones were added to selected nitroarenes in DMF/ketone mixtures leading to formation of the o

The aci-nitro equilibrium of picrylacetone: A kinetic and thermodynamic study in 50:50 and 30:70 (v/v) H2O-Me2SO mixtures

Rates of deprotonation of picrylacetone (3a) by a variety of bases B (phenoxide and carboxylate ions, primary amines, OH-, H2O) and of reprotonation of the resulting carbanion (C-3a) by the conjugate acids BH have been measured in 50 : 50 and 30 : 70 (v/v) H2O-Me2SO mixtures at 25 °C. In contrast with the situation in phenol and amine buffers, where only one relaxation time corresponding to a simple equilibrium approach according to 3a + B ? C-3a + BH is observed, a fast equilibrium protonation of the carbanion C-3a is found to precede its conversion to 3a at low pH in a number of carboxylic acid buffers and HCl solutions. The resulting short-lived nitronic acid species C-3aH has been characterized by UV-Visible stopped-flow spectrophotometry and all data (pKaNO2H , pKaCH, pKT) pertaining to the aci-nitro equilibrium of 3a in the two solvent mixtures studied could be determined. A notable solvent effect shown to be consistent with the preferential stabilization of the large polarizable carbanion C-3a by Me2SO is observed on pKaNO2H and PKaCH, but not on pKT, on going from 50 to 70% Me2SO. The solvent dependence and the magnitude of the intrinsic reactivity of 3a, as determined from the Bronsted plots for the various types of catalysts in the two solvent mixtures, are also found to agree with C-3a being an sp2-hybridized carbanion whose negative charge is largely dispersed through the picryl ring.

Solvent Effect on the Rate of Oxidation of Tetrabutylammonium 1-Acetonyl-2,4,6-trinitro-2,5-cyclohexadienide with Tetrachloro-1,4-benzoquinone

The kinetics of oxidation of 1-acetonyl-2,4,6-trinitro-2,5-cyclohexadienide with tetrachloro-1,4-benzoquinone were studied by spectrophotometry. The contribution of solvation to the kinetic parameters was estimated with the use of multiparameter regression equations. The second-order rate constants are influenced mainly by the basicity, polarizability, and polarity of aprotic solvents.

REACTIONS OF AROMATIC NITRO COMPOUNDS. LXVI. KINETICS OF OXIDATION OF THE YANOVSKII ? COMPLEX OF 1,3,5-TRINITROBENZENE BY QUINONES

The kinetic and thermodynamic parameters of the oxidation of sodium 1-acetonyl-2,4,6-trinitro-2,5-cyclohexadiene by para- and ortho-quinones in acetone were studied by a spectrophotometric method.The oxidation rate is determined mainly by the redox potentials of the quinones.

REACTIONS OF AROMATIC NITRO COMPOUNDS LXVIII. SYNTHESIS OF α-NITROARYL KETONES BY OXIDATION OF YANOVSKII ? COMPLEXES

The oxidation of the Yanovskii ? complexes of the nitro derivatives of benzene, naphthalene, and anthracene to α-aryl ketones was realized.The yield of the reaction products is determined by the ratio of the redox potentials of the ?-adduct and the oxidiz

UNEXPECTED ROUTE TO SUBSTITUTED 4,6-DINITROANTHRANILS BY OXIDATION OF ANIONIC ?-COMPLEXES OF 1,3,5-TRINITROBENZENE

Oxidation of anionic ?-complexes of trinitrobenzene with C-C bonds by the CuBr/CCl4 system forms 3-R-4,6-dinitroanthranils.When this reaction is carried out a CH2R group must be at the geminal node of the ?-complex and 18-crown-6-ether.