16552-38-8

Basic information

• Product Name: N-Picryl-m-toluidine
• Synonyms: N-Picryl-m-toluidine
• CAS NO: 16552-38-8
• Molecular Formula: C₁₃H₁₀N₄O₆
• Molecular Weight: 318.2417
• Mol File: 16552-38-8.mol

Chemical Properties

• Boiling Point: 431.7°Cat760mmHg
• Flash Point: 214.9°C
• Appearance: /
• Density: 1.535g/cm³
• Vapor Pressure: 1.17E-07mmHg at 25°C
• Refractive Index: 1.699
• CAS DataBase Reference: N-Picryl-m-toluidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Picryl-m-toluidine(16552-38-8)
• EPA Substance Registry System: N-Picryl-m-toluidine(16552-38-8)

Safety Data

• Hazardous Substances Data: 16552-38-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H10N4O6/c1-8-3-2-4-9(5-8)14-13-11(16(20)21)6-10(15(18)19)7-12(13)17(22)23/h2-7,14H,1H3

Upstream product

• 88-88-0 2,4,6-trinitrochlorobenzene 
• 108-44-1 1-amino-3-methylbenzene 
• 479-45-8 tetryl 
• 19159-68-3 dipicryl-diazene 
• 6973-40-6 2,4,6-trinitrophenyl phenyl ether 
• 5950-87-8 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether 
• 68683-32-9 2,2',4,4',6,6'-hexanitrohydrazobenzene 

Relevant articles and documents

2,4,6-Trinitro- N-(m-tolyl)aniline: A New Polymorphic Material Exhibiting Different Colors

2,4,6-Trinitro-N-(m-tolyl)aniline or N-picryl-m-toluidine (abbreviated as TMA), exhibiting color polymorphism, was synthesized and characterized structurally, spectroscopically, and thermodynamically. The studies consider both the isolated molecule of the

Electronic and steric effects in the SNAr substitution reactions of substituted anilines with 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether in acetonitrile

Rate measurements are reported for the reactions of 12 ring-substituted anilines with 2,4-dinitrophenyl 2,4,6-trinitrophenyl ether (1) in acetonitrile. Formation of the products, the correspondingly substituted 2,4,6- trinitrodiphenylamines, occurs without the observation of intermediates in detectable amounts by both base-catalysed and uncatalysed pathways and Hammett ρ value were determined for these processes. The results show that although substituents at the 3- or 4-positions of the anilines have only small steric effects, alkyl substituents at the 2-position may result in considerable reductions in reactivity. These effects are more pronounced for the base-catalysed pathway and in 2,6-dimethylaniline the uncatalysed pathway takes all the reaction flux. In the case of the 2-fluoro substituent the electronic effect, strong inductive electron withdrawal, is dominant over steric effects. Copyright

Mechanism of the Reactions of Substituted Anilines with Phenyl 2,4,6-Trinitrophenyl Ether in Benzene: Evidence for a Cyclic Transition State involving an Eight-membered Ring

Rates and activation parameters have been determined for the reactions of phenyl 2,4,6-trinitrophenyl ether with substituted anilines in benzene.For some of the nucleophiles, the rates decrease with increasing temperature in the range 5-35 deg C resulting in negative activation enthalpies (ΔH(excit.) -3.1 to -27.3 kJ mol-1).This is strong evidence for a stepwise mechanism involving (at least) a pre-equilibrium.These base-catalysed nucleophilic substitution reactions are sensitive to the nature of the arylated amine as indicated by the Hammett's constant (ρ -7.7).