2363-25-9

Basic information

• Product Name: 1-(4-methylphenoxy)-2,4-dinitrobenzene
• Synonyms: 1-(4-Methylphenoxy)-2,4-dinitrobenzene; 2,4-Dinitro-1-(p-tolyloxy)benzene; Ether, 2,4-dinitrophenyl p-tolyl
• CAS NO: 2363-25-9
• Molecular Formula: C₁₃H₁₀N₂O₅
• Molecular Weight: 274.2289
• Mol File: 2363-25-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 374.3°C at 760 mmHg
• Flash Point: 158.2°C
• Density: 1.371g/cm³
• Vapor Pressure: 1.81E-05mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 1-(4-methylphenoxy)-2,4-dinitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methylphenoxy)-2,4-dinitrobenzene(2363-25-9)
• EPA Substance Registry System: 1-(4-methylphenoxy)-2,4-dinitrobenzene(2363-25-9)

Safety Data

• Hazardous Substances Data: 2363-25-9(Hazardous Substances Data)

Usage

Chemical structure

A benzene ring with two nitro groups (-NO2) at the 2nd and 4th positions, and a phenoxy group (-OC6H4-CH3) attached to the 1st position.

Reactivity

Highly reactive due to the presence of nitro groups and phenoxy group, making it a useful building block for more complex molecules in organic chemistry.

Color

Yellow.

Solubility

Insoluble in water, but soluble in organic solvents.

Applications

Commonly used in the synthesis of organic compounds and as a reagent in chemical reactions.

Safety precautions

Toxic and can cause skin and eye irritation, so it should be handled with caution.

Molecular weight

Approximately 273.22 g/mol.

Appearance

Yellow crystalline solid.

Hazardous properties

Classified as an irritant and toxic substance.

Upstream product

• 106-44-5 p-cresol 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 1121-70-6 sodium 4-methylphenoxide 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 1192-96-7 potassium p-cresolate 
• 2363-36-2 (2,4-dinitro-phenyl)-(4-nitro-phenyl)-ether 
• 584-48-5 2,4-dinitrobromobenzene 

Downstream Products

• 3761-31-7 4-(2,4-dinitrophenoxy)benzoic acid 
• 6282-16-2 (2,4-dinitro-phenyl)-(4-methyl-2-nitro-phenyl)-ether 
• 408349-30-4 (2,4-dinitro-phenyl)-(4-methyl-2,3-dinitro-phenyl)-ether 
• 119-27-7 2,4-dinitroanisole 
• 68191-07-1 4-methyl-2,5-dinitrophenol 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 51-28-5 2,4-Dinitrophenol 
• 4096-88-2 1-azido-2,4-dinitrobenzene 
• 610-54-8 2,4-dinitro-1-ethoxybenzene 

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.

Synthesis and biological evaluation of novel thiadiazole amides as potent Cdc25B and PTP1B inhibitors

A series of novel thiadiazole amide derivatives have been synthesized and evaluated for inhibitory activities against Cdc25B and PTP1B. Most of them showed inhibitory activities against Cdc25B (IC50 = 1.18-8.01 μg/mL) and PTP1B (IC50 = 0.85-8.75 μg/mL), respectively. Moreover, compounds 5b and 4l were most potent with IC50 values of 1.18 and 0.85 μg/mL for Cdc25B and PTP1B, respectively, compared with reference drugs Na3VO4 (IC50 = 0.93 μg/mL) and oleanolic acid (IC50 = 0.85 μg/mL). The results of selectivity experiments showed that the target compounds were selective inhibitors against PTP1B and Cdc25B. Enzyme kinetic experiments demonstrated that compound 5k was a specific inhibitor with the typical characteristics of a mixed inhibitor.

Kinetic study on SNAr reaction of 1-Y-substituted-phenoxy-2,4- dinitrobenzenes with hydroxide ION: Effect of substituent y on reactivity and reaction mechanism

A kinetic study is reported for the SNAr reaction of 1-Y-substituted- phenoxy-2,4-dinitrobenzenes (1a-1h) with OH- in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The second-order rate constant (kOH-) increases as the substituent Y in the leaving group changes from an electron-donating group (EDG) to an electronwithdrawing group (EWG). The Bronsted-type plot for the reactions of 1a-1h is linear with βlg = -0.16, indicating that the reactivity of substrates 1a-1h is little affected by the leaving-group basicity. A linear Bronsted-type plot with βlg = -0.3 ± 0.1 is typical for reactions reported previously to proceed through a stepwise mechanism in which formation of a Meisenheimer complex is the rate-determining step (RDS). The Hammett plot correlated with σY o constants results in a much better correlation than that correlated with σY - constants, implyng that no negative charge is developing on the O atom of the leaving group (or expulsion of the leaving group is not advanced at all in the TS). This excludes a possibility that the SNAr reaction of 1a-1h with OH- proceeds through a concerted mechanism or via a stepwise pathway with expulsion of the leaving group being the RDS. Thus, the current reactions have been concluded to proceed through a stepwise mechanism in which expulsion of the leaving group occurs rapidly after the RDS.