2363-36-2

Basic information

• Product Name: 2,4-dinitro-1-(4-nitrophenoxy)benzene
• Synonyms: 2,4-Dinitro-1-(4-nitro-phenoxy)-benzene; 2,4-dinitrophenyl 4-nitrophenyl ether; benzene, 2,4-dinitro-1-(4-nitrophenoxy)-; Ether, 2,4-dinitrophenyl p-nitrophenyl
• CAS NO: 2363-36-2
• Molecular Formula: C₁₂H₇N₃O₇
• Molecular Weight: 305.1999
• Mol File: 2363-36-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 424.3°C at 760 mmHg
• Flash Point: 188.2°C
• Density: 1.56g/cm³
• Vapor Pressure: 5.15E-07mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: 2,4-dinitro-1-(4-nitrophenoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dinitro-1-(4-nitrophenoxy)benzene(2363-36-2)
• EPA Substance Registry System: 2,4-dinitro-1-(4-nitrophenoxy)benzene(2363-36-2)

Safety Data

• Hazardous Substances Data: 2363-36-2(Hazardous Substances Data)

Usage

General Description

2,4-dinitro-1-(4-nitrophenoxy)benzene is a chemical compound with the molecular formula C12H6N4O8. It is a yellow crystalline solid that is insoluble in water but soluble in organic solvents. It is primarily used as an intermediate in the production of dyes, pigments, and other organic compounds. It is also known for its explosive properties and is used in the manufacture of explosives and propellants. Exposure to this compound can cause irritation to the skin, eyes, and respiratory system, and it is considered to be a potential environmental pollutant. It is important to handle and dispose of this chemical with care to prevent harm to human health and the environment.

Upstream product

• 14609-74-6 p-nitrophenolate 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 2486-07-9 2,4-dinitrophenyl phenyl ether 
• 7697-37-2 nitric acid 
• 101-84-8 diphenylether 
• 1124-31-8 potassium 4-nitrophenolate 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 2831-60-9 2-(2,4-dinitrophenoxy)ethanol 
• 2217-56-3 bis(2,4-dinitrophenyl) ether 
• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 26227-87-2 Dnp-Gly-Gly-OH 
• 51-28-5 2,4-Dinitrophenol 
• 117593-93-8 1-(2,4-dinitro-phenyl)-3-methyl-piperidine, N-(2.4-dinitro-phenyl)-dl-β-pipecoline 
• 31284-04-5 N-(2,4-dinitrophenyl)piperidine 
• 331652-62-1 2-[4-(2,4-dinitrophenyl)piperazin-1-yl]ethanol 
• 39242-76-7 4-(2,4-dinitrophenyl)morpholine 
• 610-54-8 2,4-dinitro-1-ethoxybenzene 
• 2363-25-9 1-(4-methylphenoxy)-2,4-dinitrobenzene 
• 2486-07-9 2,4-dinitrophenyl phenyl ether 

Relevant articles and documents

Kinetic study on SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes with Azide ion: Effect of changing nucleophile from hydroxide to Azide ion on reaction mechanism and reactivity

Second-order rate constants (kN3-) for SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes (2a-2h) with (Formula presented.) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C have been measured spectrophotometrically. The Bronsted-type plot is linear with β1g=-0.38. The Hammett plots correlated with (Formula presented.) constants exhibit highly scattered points. In contrast, the Yukawa-Tsuno plot results in an excellent linear correlation with ρY = 1.02 and r = 0.51, indicating that a negative charge develops partially on the O atom of the leaving Y-substituted-phenoxy moiety in the transition state. Accordingly, the reactions have been concluded to proceed through a stepwise mechanism, in which expulsion of the leaving group occurs in the rate-determining step. Comparison of kN3- with the kOH- values reported previously for the corresponding reactions with OH has revealed that (Formula presented.) is only 6- to 26-fold than OH toward substrates 2a-2h, although the former is over 11 pKa units less basic than the latter. Solvation and polarizability effects have been suggested to be responsible for the unusual reactivity shown by (Formula presented.) and OH. Effects of changing nucleophile from OH to (Formula presented) on reaction mechanism and reactivity are discussed in detail.

The α-effect in SNar reaction of y-substituted-phenoxy-2, 4-dinitrobenzenes with amines: Reaction mechanism and origin of the α-effect

Second-order rate constants (kN) have been measured spectrophotometrically for SNAr reactions of Ysubstituted-phenoxy-2, 4-dinitrobenzenes (1a-1g) with hydrazine and glycylglycine in 80 mol % H 2O/20 mol % DMSO at 25.0 ± 0.1 °C. Hydrazine is 14.6-23.4 times more reactive than glycylglycine. The magnitude of the α-effect increases linearly as the substituent Y becomes a stronger electron-withdrawing group (EWG). The Bronsted-type plots for the reactions with hydrazine and glycylglycine are linear with βlg = -0.21 and -0.14, respectively, which is typical for reactions reported previously to proceed through a stepwise mechanism with expulsion of the leaving group occurring after rate-determining step (RDS). The Hammett plots correlated with so constants result in much better linear correlations than s- constants, indicating that expulsion of the leaving group is not advanced in the transition state (TS). The reaction of 1a-1g with hydrazine has been proposed to proceed through a five-membered cyclic intermediate (TIII), which is structurally not possible for the reaction with glycylglycine. Stabilization of the intermediate TIII through intramolecular H-bonding interaction has been suggested as an origin of the α-effect exhibited by hydrazine.

Kinetic study on SNAr reaction of 1-(Y-Substituted-phenoxy)-2,4- dinitrobenzenes with cyclic secondary amines in acetonitrile: Evidence for cyclic transition-state structure

A kinetic study is reported for SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes (1a-1h) with amines in MeCN. The plots of pseudo-first-order rate constant versus amine concentration curve upward, indicating that the reactions are catalyzed by a second amine molecule. The Br?nsted-type plots for the reaction of 1-(4-nitrophenyl)-2,4- dinitrobenzene (1a) with secondary amines are linear with βnuc = 1.10 and 0.85 for the uncatalyzed and catalyzed reactions, respectively, while the Yukawa-Tsuno plots for the reactions of 1a-1h with piperidine result in excellent linear correlations with ρY = 1.85 and r = 0.27 for the uncatalyzed reaction and ρY = 0.73 and r = 0.23 for the catalyzed reaction. The catalytic effect decreases with increasing amine basicity or electron-withdrawing ability of the substituent Y in the leaving group. Activation parameters calculated from the rate constants measured at five different temperatures for the catalyzed reaction of 1a with piperidine are ΔH? = 0.38 kcal/mol and ΔS? = -55.4 cal/(mol K). The catalyzed reaction from a Meisenheimer complex (MC ±) is proposed to proceed through a concerted mechanism with a cyclic transition-state rather than via a stepwise pathway with an anionic intermediate, MC-. Deuterium kinetic isotope effects provide further insight into the nature of the concerted transition state.