13218-13-8

Basic information

• Product Name: Nitroacetonitrile
• Synonyms: 2-Nitroacetonitrile;Nitroacetonitrile;Acetonitrile, nitro-
• CAS NO: 13218-13-8
• Molecular Formula: C₂H₂N₂O₂
• Molecular Weight: 86.05
• Mol File: 13218-13-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 224.4 °C at 760 mmHg
• Flash Point: 89.5 °C
• Appearance: /
• Density: 1.270
• PKA: 4.62±0.29(Predicted)
• CAS DataBase Reference: Nitroacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Nitroacetonitrile(13218-13-8)
• EPA Substance Registry System: Nitroacetonitrile(13218-13-8)

Safety Data

• Hazardous Substances Data: 13218-13-8(Hazardous Substances Data)

Usage

General Description

Nitroacetonitrile is a chemical compound with the molecular formula C2H2N2O2. It is a highly reactive and toxic compound that is used in the synthesis of pharmaceuticals and agrochemicals. Nitroacetonitrile is known for its ability to undergo various chemical reactions, including nucleophilic addition and substitution reactions. It is commonly used in the production of nitroacetic acid and its derivatives, which have applications in medicinal chemistry and organic synthesis. Due to its toxic nature, nitroacetonitrile must be handled with care and proper safety measures should be followed when working with this compound.

Upstream product

• 5653-21-4 2-nitroacetaldehyde oxime 
• 7570-26-5 1,2-dinitroethane 
• 7719-09-7 thionyl chloride 
• 5653-21-4 metazonic acid 
• 60-29-7 diethyl ether 
• 97925-51-4 2-Nitro-3-oxo-propionitrile 

Downstream Products

• 109568-63-0 2,2'-dinitro-2,2'-cyclohexylidene-di-acetonitrile; bis-diethylamine salt 
• 58046-27-8 4-hydroxy-3-methoxy-α-nitro-cis-cinnamonitrile 
• 100865-52-9 3-anilino-3-(2-chloro-phenyl)-2-nitro-propionitrile 
• 100881-55-8 3-anilino-2-nitro-3-(4-nitro-phenyl)-propionitrile 
• 70827-33-7 3-methyl-2-nitro-5t-phenyl-penta-2ξ,4-dienenitrile 
• 102003-15-6 2-nitro-5-oxo-2-(3-oxo-3-phenyl-propyl)-5-phenyl-valeronitrile 
• 22918-12-3 2-nitromethylbenzothiazole 
• 19747-21-8 4-nitro-3-phenyl-isoxazol-5-ylamine 
• 126065-38-1 C₈H₈N₄O₄^(2-)*2C₄H₉Cl₂N*2H⁽¹⁺⁾ 
• 6123-71-3 3-Anilino-2-nitro-propennitril 
• 917839-31-7 4-[(E)-2-cyano-2-nitrovinyl]benzonitrile 
• 14677-11-3 4-phenyl-1H-1,2,3-triazole-5-carbonitrile 
• 38436-36-1 (2E)-3-phenyl-2-nitroprop-2-enenitrile 
• 98207-42-2 (E)-1-cyano-2-(4'-chlorophenyl)-1-nitroethene 

Relevant articles and documents

Synthesis of α-functional nitro compounds by the nitration of activated carbonyl compounds in a two-phase system

2-Nitro-1,3-dicarbonyl and α-nitromonocarbonyl compounds were synthesized in the yields variyng from moderate (30percent) to nearly quantitative by the nitration of β-dicarbonyl compounds in a two-phase system: sulfuric/nitric acid mixture - chloroform at -10 - 10 deg C.The use of phase transfer conditions made it possible to avoid the formation of furoxans as by-products and to simplify the isolation of products.This method is quite common for preparing various α-functional nitro compounds including those containing a CF3-group. - Key words: nitration, α-functional nitro compounds.

A high density pyrazolo-triazine explosive (PTX)

The fused-ring heterocycle 4-amino-3,7,8-trinitropyrazolo-[5,1-c][1,2,4]triazine (PTX) has promising explosive properties. The Cheetah thermochemical code used its calculated standard enthalpy of formation and its measured crystal density of 1.946 g cm-3 to predict HMX-like explosive performance, while measurements of its thermal stability, sensitivity to impact, friction, and spark showed greater safety margins.

Nitroacetonitrile and Its Synthetic Equivalents

Nitroacetonitrile (NAN) serves as a cyano(nitro)methylating agent facilitating the construction of polyfunctionalized compounds; however, its explosive property is a significant drawback in terms of practical handling. Alkali metal salts of NAN are therma

Development of a safely handleable synthetic equivalent of cyanonitrile oxide by 1,3-dipolar cycloaddition of nitroacetonitrile

Dianionic cyano-aci-nitroacetate affords 3-cyanoisoxazol(in)es upon heating with a range of dipolarophiles in the presence of hydrochloric acid. In this reaction, nitroacetonitrile is formed as an intermediate active species, which serves as a synthetic e