155593-11-6

Basic information

• Product Name: 2-(2,6-dinitrophenyl)acetonitrile
• Synonyms: 2-(2,6-dinitrophenyl)acetonitrile;2,6-DINITROPHENYLACETONITRILE
• CAS NO: 155593-11-6
• Molecular Formula: C₈H₅N₃O₄
• Molecular Weight: 207.145
• Mol File: 155593-11-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,6-dinitrophenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-dinitrophenyl)acetonitrile(155593-11-6)
• EPA Substance Registry System: 2-(2,6-dinitrophenyl)acetonitrile(155593-11-6)

Safety Data

• Hazardous Substances Data: 155593-11-6(Hazardous Substances Data)

Usage

General Description

2-(2,6-dinitrophenyl)acetonitrile is a chemical compound with the molecular formula C8H4N4O4. It is a yellow solid that is not very soluble in water, but dissolves readily in organic solvents. This chemical is commonly used in organic synthesis and as a building block for the preparation of other compounds. It is also known for its explosive properties and is considered a potentially hazardous compound. Additionally, 2-(2,6-dinitrophenyl)acetonitrile has been identified as a potential mutagen and is classified as a toxic substance. Due to its hazardous nature, it is important to handle and store this chemical with proper safety precautions.

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 624-75-9 iodoacetonitrile 
• 75-05-8 acetonitrile 
• 606-20-2 2,6-dinitrotoluene 
• 590-17-0 cyanomethyl bromide 
• 93213-74-2 2-(bromomethyl)-1,3-dinitrobenzene 
• 151-50-8 potassium cyanide 

Downstream Products

• 603-12-3 2,6-dinitrobenzoic acid 

Relevant articles and documents

Synthesis of 2-(2,6-dinitrophenyl)malonates, -acetates and acetonitrile by copper-mediated vicarious nucleophilic substitution

A regioselective, vicarious nucleophilic substitution of 1,3- dinitrobenzene with α-bromo- and iodocarbanions proceeds in the presence of copper(1) tert-butoxide and pyridine giving 2,6-dinitrophenylmalonates, 2,6- dinitrophenylacetates or 2,6-dinitrophenylacetonitrile as the only isomers from bromomalonate esters, bromoacetate esters, iodoacetate esters or iodoacetonitrile, respectively. Without copper(I) tert-butoxide, the 4- substituted isomer is the only product. We believe that the reaction proceeds via a σ-adduct of 1,3-dinitrobenzene and halocarbanion from which hydrogen and halogen are eliminated. This elimination is dependent upon the concentration of copper(I) tert-butoxide.

Unexpected formation of the arcyriacyanin system by condensation of a 3-bromo-4-(indol-3-yl)maleimide with (2-nitrophenyl)acetates

The reaction of an N-protected 3-bromo-4-(indol-3-yl)maleimide with methyl (2-nitrophenyl)acetates in the presence of base affords condensed cycloheptatriene derivatives which can be transformed into arcyriacyanin-type alkaloids. The unusual reaction sequ