20650-73-1

Basic information

• Product Name: 2,6-dinitrophenoxide ion
• Synonyms: 2,6-dinitrophenoxide ion
• CAS NO: 20650-73-1
• Molecular Weight: 183.1
• Mol File: 20650-73-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,6-dinitrophenoxide ion(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dinitrophenoxide ion(20650-73-1)
• EPA Substance Registry System: 2,6-dinitrophenoxide ion(20650-73-1)

Safety Data

• Hazardous Substances Data: 20650-73-1(Hazardous Substances Data)

Upstream product

• 1523-09-7 2,6-dinitrophenyl acetate 
• 18938-17-5 4-formylphenoxide ion 
• 14609-76-8 4-cyanophenolate 
• 110-89-4 piperidine 
• 3535-67-9 2,6-dinitroanisole 

Relevant articles and documents

Mechanism of reaction of hydroxide ion with dinitrochlorobenzenes

Formation of dinitrophenoxide ion from 2,4- and 2,6-dinitrochlorobenzene (2,4- and 2,6-DNCB) and OH- (OD-) in 70:30 and 80:20 (v/v) DMSO-H2O (D2O) is accompanied by extensive 1H NMR line broadening of unreacted substrate and exchange of arene hydrogen with D2O, which is quantitative at the 3-position of 2,4-DNCB. Unproductive Meisenheimer complexes are detected spectrophotometrically in the course of reaction. For reaction of 2,4-DNCB, the Meisenheimer 3-complex is formed first and then the more stable 5-complex can be detected and characterized by NMR spectrometry. There is no hydrogen exchange of Meisenheimer complexes or dinitrophenoxide ions and their 1H NMR signals are not broadened. These results do not fit the classical mechanism of single-step nucleophilic addition, but they, and the kinetic results, are fitted by a reaction scheme involving single-electron transfer from OH- to give a charge-transfer complex of OH? and a radical anion which collapses to give Meisenheimer complexes and aryl oxide ion. This scheme is consistent with MO calculations by the AM1 method.

Reactions of Nitroanisoles. Part 2. Reactions of 2,4- and 2,6-Dinitroanisole with Piperidines in Benzene

The reactions of 2,4- (I) and 2,6-dinitroanisole (VIII) with piperidine (II) and N-methylpiperidine (NMP) in benzene have been studied.It was found that (I) and (VIII) react with (II) to give not only the expected aromatic nucleophilic substitution (a.n.s.) products, but also the corresponding dinitrophenols, generated by an SN2 reaction.The rate for each reaction and the overall rates were measured and it was observed that compound (I) has similar rate coefficients for the a.n.s. as well as for the SN2 reaction.Mild acceleration by base was found for the a.n.s.reaction.When (VIII) reacts with (II) the rate of reaction to form 2,6-dinitrophenol is greater than the rate for the a.n.s.In the reaction with NMP only an SN2 reaction was observed.Furthermore, the rates of reaction of (VIII) with (II) and with NMP are ca. 1000 and 300 times, respectively, the rate of reaction of (I) with these amines.A field effect is proposed for the increase in rate.