2486-07-9

Basic information

• Product Name: 2,4-dinitro-1-phenoxybenzene
• Synonyms: 2,4-dinitro-1-phenoxybenzene;2,4-dinitrophenyl phenyl ether;1,3-Dinitro-4-phenoxybenzene;1-Phenoxy-2,4-dinitrobenzene;Phenyl 2,4-dinitrophenyl ether
• CAS NO: 2486-07-9
• Molecular Formula: C₁₂H₈N₂O₅
• Molecular Weight: 260.20232
• EINECS: 219-627-8
• Mol File: 2486-07-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 71°C
• Boiling Point: 403.46°C (rough estimate)
• Flash Point: 158.3°C
• Appearance: /
• Density: 1.3933 (rough estimate)
• Vapor Pressure: 4.16E-05mmHg at 25°C
• Refractive Index: 1.6360 (estimate)
• CAS DataBase Reference: 2,4-dinitro-1-phenoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dinitro-1-phenoxybenzene(2486-07-9)
• EPA Substance Registry System: 2,4-dinitro-1-phenoxybenzene(2486-07-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36
• Safety Statements: 26-37/39
• Hazardous Substances Data: 2486-07-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 26, p. 301, 1996 DOI: 10.1080/00397919608003618

InChI:InChI=1/C12H8N2O5/c15-13(16)9-6-7-12(11(8-9)14(17)18)19-10-4-2-1-3-5-10/h1-8H

Upstream product

• 110-86-1 pyridine 
• 742-25-6 2,4-dinitrophenyl 4-methylbenzenesulfonate 
• 584-48-5 2,4-dinitrobromobenzene 
• 100-67-4 potassium phenolate 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 108-95-2 phenol 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 67-56-1 methanol 
• 3229-70-7 phenolate 
• 139-02-6 sodium phenoxide 
• 22351-79-7 2,4-dinitrophenyl trifluoromethyl sulfone 
• 1174-72-7 tetraphenoxysilane 
• 13509-27-8 methyl phenyl carbonate 
• 3115-68-2 tetrabutyl phosphonium bromide 

Downstream Products

• 2831-60-9 2-(2,4-dinitrophenoxy)ethanol 
• 961-68-2 N-phenyl-2,4-dinitroaniline 
• 5465-68-9 2-(2,4-dinitrophenyl)-3-oxobutyric acid ethyl ester 
• 7474-11-5 1-(2,4-dinitrophenyl)-3,5-dimethylpyrazole 
• 13059-86-4 2,4-dinitro-N-butylaniline 
• 2363-36-2 (2,4-dinitro-phenyl)-(4-nitro-phenyl)-ether 
• 6973-40-6 2,4,6-trinitrophenyl phenyl ether 
• 10242-31-6 1-(4-nitrophenoxy)-2,4,6-trinitrobenzene 
• 2217-56-3 bis(2,4-dinitrophenyl) ether 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 108-95-2 phenol 
• 4096-88-2 1-azido-2,4-dinitrobenzene 
• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 92432-49-0 2,4-Dinitro-N-octyl-⁽²⁾-anilin 

Relevant articles and documents

An efficient strategy for the synthesis of aryl ethers

An efficient strategy for the construction of aryl ethers using aryl fluorides and silyl ethers is described. This protocol uses a sub-stoichiometric amount of silicon-based reagent and proceeds under milder conditions than previously reported reactions of this type. Georg Thieme Verlag Stuttgart.

Choline Hydroxide as a Versatile Medium for Catalyst-Free O-Functionalization of Phenols

A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal- and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.

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.