14798-26-6

Basic information

• Product Name: 2,4,6-Trinitrophenoxide
• Synonyms: 2,4,6-Trinitrophenolate;2,4,6-Trinitrophenoxide;Picric acidanion;[2-(2-phenylethyl)phenyl]azanium;bis(3-azaniumylpropyl)-[2-(dimethylazaniumyl)ethyl]azanium
• CAS NO: 14798-26-6
• Molecular Formula: C₆H₂N₃O₇
• Molecular Weight: 0
• Mol File: 14798-26-6.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 303.56°C at 760 mmHg
• Flash Point: 133.896°C
• Appearance: /
• Vapor Pressure: 0.001mmHg at 25°C
• CAS DataBase Reference: 2,4,6-Trinitrophenoxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trinitrophenoxide(14798-26-6)
• EPA Substance Registry System: 2,4,6-Trinitrophenoxide(14798-26-6)

Safety Data

• Hazardous Substances Data: 14798-26-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H/p-1

Upstream product

• 115828-60-9 (E)-O-Picrylbenzaldoxime 
• 115828-61-0 4-methoxy-benzaldehyde-(O-picryl-seqtrans-oxime ) 
• 115828-63-2 4-nitro-benzaldehyde-(O-picryl-seqtrans-oxime ) 
• 131602-64-7 1-(2-acetoxyethoxy)-2,4,6-trinitrobenzene 
• 88-89-1 2,4,6-Trinitrophenol 
• 16331-65-0 t-butoxide 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 115828-62-1 3-Bromo-benzaldehyde O-(2,4,6-trinitro-phenyl)-oxime 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 100-67-4 potassium phenolate 
• 24676-69-5 potassium 2,6-di-tert-butylphenolate 
• 364-44-3 picryl fluoride 
• 79719-34-9 trimethyl-2,4,6 phenate de potassium 
• 67263-27-8 2,4,6-trinitro-1-piperidinobenzene 

Downstream Products

• 12241-77-9 {(C₆H₆)2Cr}⁽¹⁺⁾*{OC₆H₂(NO₂)3}^(1-)={(C₆H₆)2Cr}{OC₆H₂(NO₂)3} 
• 107065-12-3 {Ag(C₁₅H₂₆P₂)2}⁽¹⁺⁾*OC₆H₂(NO₂)3^(1-)={Ag(C₁₅H₂₆P₂)2}OC₆H₂(NO₂)3 
• 15938-03-1 2-methylazinium (2,4,6)-trinitrophenolate 
• 730918-86-2 C₆H₄N₃O₇^(3-) 
• 88-89-1 2,4,6-Trinitrophenol 

Relevant articles and documents

Concerted mechanisms of the reactions of 2,4,6-trinitrophenyl methyl carbonate and 2,4,6-trinitrophenyl acetate with secondary alicyclic amines

The reactions of secondary alicyclic amines with 2,4,6-trinitrophenyl methyl carbonate (TNPMC) and 2,4,6-trinitrophenyl acetate (TNPA) are subjected to a kinetic study in aqueous solution, 25.0 °C, ionic strength 0.2 (KCl). The reactions are studied by following spectrophotometrically (360 nm) the release of the 2,4,6-trinitrophenoxide anion. Under amine excess, pseudo-first-order rate coefficients (kobsd) are found. Plots of kobsd vs [amine] are linear, with the slope (kN) independent of pH. The Broensted-type plots (log kN vs pKa of the conjugate acid of the amines) are linear, with slopes β = 0.41 and β = 0.36 for the reactions of TNPA and TNPMC, respectively. The predicted breaks of the Broensted plots for stepwise mechanisms are pKa0 = 6.8 and 7.3, respectively. The lack of Broensted breaks for these reactions and the values of the Broensted slopes are consistent with concerted mechanisms. By comparison of the reactions under investigation among them and with similar aminolysis and pyridinolysis, the following conclusions can be drawn: (i) Secondary alicyclic amines react with TNPA and TNPMC by concerted mechanisms. (ii) TNPA is more reactive toward these amines than TNPMC due to the greater electron release of MeO from the latter substrate. (iii) The change of 2,4-dinitrophenoxy to 2,4,6-trinitrophenoxy in the zwitterionic tetrahedral intermediate (T± formed in the reactions of the title amines with 2,4-dinitrophenyl acetate greatly destabilizes T±. (iv) Secondary alicyclic amines destabilize T± relative to pyridines. (v) The intermediate T± formed in the reactions of the title amines with S-(2,4,6-trinitrophenyl) acetate is greatly destabilized by substitution of S-(2,4,6-trinitrophenyl) by O-(2,4,6-trinitrophenyl) as the leaving group.

Kinetics of the reaction of phenyl picrates with phenoxide ions in water. Concerted or stepwise?

A kinetic study is reported of the exchange reactions of substituted phenoxide ions with some ring-substituted 2,4,6-trinitrophenyl ethers in water. The βronsted diagrams formed by plotting log k, where k is the second-order rate constant for reaction, ve

Kinetics and mechanism of the benzenethiolysis of 2,4-dinitrophenyl and 2,4,6-trinitrophenyl methyl carbonates and S-(2,4-dinitrophenyl) and S-(2,4,6-trinitrophenyl) ethyl thiolcarbonates

The reactions of 2,4-dinitrophenyl and 2,4,6-trinitrophenyl methyl carbonates (DNPC and TNPC, respectively) and S-(2,4-dinitrophenyl) and S-(2,4,6-trinitrophenyl) ethyl thiolcarbonates (DNPTC and TNPTC, respectively) with a series of benzenethiolate anions were subjected to a kinetic investigation in water, at 25.0 °C, and an ionic strength of 0.2 M (KCl). These reactions obey pseudo-first-order kinetics, under excess of benzenethiolate, and are first order in the latter reactant. However, comparable reactant concentrations were used in the reactions of 4-nitrobenzenethiolate anion with TNPC and TNPTC, which showed second-order kinetics. The nucleophilic rate constants are pH independent, except those for the reactions of TNPC with 4-methoxy- and pentafluorobenzenethiolates, and TNPTC with benzenethiolate and 4-chloro- and 3-chlorobenzenethiolates, which show acid dependence. The Bronsted-type plots for the nucleophilic rate constants are linear with slopes β = 0.9, 1.0, 0.9, and 0.9 for the reactions of DNPC, TNPC, DNPTC, and TNPTC, respectively. No break in the Bronsted plot was found for the reactions of DNPC and DNPTC at pKa ca. 4.1 and 3.4, respectively, consistent with concerted mechanisms. TNPC is more reactive toward benzenethiolate anions than DNPC, and TNPTC more than DNPTC due to the better leaving groups involved. Comparison of the kinetic results obtained in this work with those for the concerted phenolysis of the same substrates shows that benzenethiolate anions are better nucleophiles toward carbonates than isobasic phenoxide anions. This is explained by Pearson's hard and soft acids and bases principle.