2363-38-4

Basic information

• Product Name: 1-(3-chlorophenoxy)-2,4-dinitrobenzene
• CAS NO: 2363-38-4
• Molecular Formula: C₁₂H₇ClN₂O₅
• Molecular Weight: 294.6474
• Mol File: 2363-38-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 390.3°C at 760 mmHg
• Flash Point: 189.8°C
• Density: 1.505g/cm³
• Vapor Pressure: 6.02E-06mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 1-(3-chlorophenoxy)-2,4-dinitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-chlorophenoxy)-2,4-dinitrobenzene(2363-38-4)
• EPA Substance Registry System: 1-(3-chlorophenoxy)-2,4-dinitrobenzene(2363-38-4)

Safety Data

• Hazardous Substances Data: 2363-38-4(Hazardous Substances Data)

Usage

General Description

1-(3-chlorophenoxy)-2,4-dinitrobenzene is a chemical compound that consists of a benzene ring with a 3-chlorophenoxy group and two nitro groups attached. It is commonly known as chlornitrofen and is used as a herbicide to control weeds in agricultural and industrial settings. Chlornitrofen is a selective herbicide, meaning it only targets specific types of plants while leaving others unharmed. It works by inhibiting the growth of target weeds, ultimately leading to their death. However, it has been subject to regulatory restrictions and potential bans in some countries due to its environmental and health concerns. Studies have shown that chlornitrofen can have harmful effects on aquatic organisms and may pose a risk to human health if not used properly. Therefore, its use is heavily regulated and alternatives are being sought in many parts of the world.

Upstream product

• 70-34-8 2,4-Dinitrofluorobenzene 
• 108-43-0 3-monochlorophenol 
• 2363-36-2 (2,4-dinitro-phenyl)-(4-nitro-phenyl)-ether 
• 126644-71-1 1-<(tert-butyldimethylsilyl)oxy>-3-chlorobenzene 

Downstream Products

• 610-54-8 2,4-dinitro-1-ethoxybenzene 
• 4096-88-2 1-azido-2,4-dinitrobenzene 
• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 51-28-5 2,4-Dinitrophenol 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 26227-87-2 Dnp-Gly-Gly-OH 
• 119-27-7 2,4-dinitroanisole 

Relevant articles and documents

The α-effect in the SNAr reaction of 1-(4-nitrophenoxy)-2,4-dinitrobenzene with anionic nucleophiles: Effects of solvation and polarizability on the α-effect

A kinetic study on SNAr reactions of 1-(4-nitrophenoxy)-2,4-dinitrobenzene (1a) with various anionic nucleophiles in 80 mol% water-20 mol% DMSO at 25.0 °C is reported. The Bronsted-type plot for the reaction of 1a with a series of substituted phenoxides and HOO- results in an excellent linear correlation with βnuc = 1.17. However, OH- exhibits dramatic negative deviation from the Bronsted-type plot, while N3-, C6H5S-, and butane-2,3-dione monoximate (Ox-) deviate positively from linearity. HOO- is 680-fold more reactive than OH- but does not exhibit the α-effect. In contrast, Ox- is 166-fold more reactive than isobasic 4-Cl-C6H4O- and exhibits the α-effect. Differential solvation effects have been suggested to be responsible for the α-effect in this study, i.e., Ox- exhibits the α-effect, since it is 5.7 kcal/mol less strongly solvated than 4-Cl-C6H4O- in the reaction medium, while HOO- does not show the α-effect due to a strong requirement for partial desolvation before nucleophilic attack. The highly enhanced reactivity of polarizable N3- and C6H5S- and extremely decreased reactivity of nonpolarizable OH- are in accord with the hard-soft acid and base principle.

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.