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

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

Uses

Used in Pharmaceutical Synthesis:
Nitroacetonitrile is used as a key intermediate in the synthesis of pharmaceuticals for its reactivity in facilitating the formation of desired medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, Nitroacetonitrile serves as a precursor in the production of various agrochemicals, contributing to the development of effective crop protection agents.
Used in Organic Synthesis:
Nitroacetonitrile is utilized as a reactive building block in organic synthesis, enabling the creation of a wide range of organic compounds for different applications.
Safety Note:
Due to its toxic nature, Nitroacetonitrile must be handled with extreme care, and stringent safety measures should be adhered to during its use in any application to ensure the safety of individuals and the environment.

Upstream product

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

Downstream Products

• 38436-36-1 (2E)-3-phenyl-2-nitroprop-2-enenitrile 
• 102003-15-6 2-nitro-5-oxo-2-(3-oxo-3-phenyl-propyl)-5-phenyl-valeronitrile 
• 52617-52-4 5-nitro-4-(4-nitro-phenyl)-2-oxy-4,5-dihydro-isoxazole-3-carbonitrile 
• 52617-51-3 5-nitro-4-(3-nitro-phenyl)-2-oxy-4,5-dihydro-isoxazole-3-carbonitrile 
• 6123-71-3 3-Anilino-2-nitro-propennitril 
• 103867-44-3 2-nitro-3-(4-fluorophenyl)acrylonitrile 
• 126065-38-1 C₈H₈N₄O₄^(2-)*2C₄H₉Cl₂N*2H⁽¹⁺⁾ 
• 448897-29-8 (E)-3-(3-Methoxy-phenyl)-2-nitro-acrylonitrile 
• 57222-07-8 (2E)-3-(4-methylphenyl)-2-nitroacrylonitrile 
• 57222-08-9 (E)-1-cyano-2-(4'-methoxyphenyl)-1-nitroethene 
• 64273-53-6 2-Nitro-3-p-chloranilinoacrylnitril 
• 64273-54-7 2-Nitro-3-p-toluidinoacrylnitril 
• 70827-33-7 3-methyl-2-nitro-5t-phenyl-penta-2ξ,4-dienenitrile 
• 112325-87-8 3-methyl-2,4-dinitro-3-phenyl-glutaronitrile 

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.

Syntheses with nitriles, LXXXVIII; cyanonitropropenides - Synthons for the preparation of nitropyridines

Nitroacetonitrile reacts with triethyl orthoformate, orthoacetate and orthopropionate, respectively in presence of pyridine to the pyridinium salts of 1,3-dicyano-1,3-dinitro-2-propen-1-ides. With ethoxymethylenemalononitrile nitroacetonitrile yields 1,1,3-tricyano-3-nitropropenide, which can be cyclized with sodium methoxide or ethoxide to 2-alkoxy-6-amino-3-cyano-5-nitropyridines. Ether cleavage of the latter leads to 6-amino-3-cyano-5-nitro-2(1H)-pyridone, subsequent chlorination gives the corresponding 2-chloropyridine, suitable for nucleophilic substitutions. By hydrolysis of the nitrile group 6-amino-5-nitro-3-pyridine-carboxylic acid derivatives are obtained.

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

Method for efficiently synthesizing nitroacetonitrile

The invention discloses a method for efficiently synthesizing nitroacetonitrile, which comprises the following steps: by using nitromethane as a starting raw material, carrying out Henry reaction under the action of alkali to obtain nitroacetaldehyde oxime, and dehydrating the nitroacetaldehyde oxime under the action of thionyl chloride to obtain nitroacetonitrile. The method is designed by starting from a commercially available low-cost raw material nitromethane, wherein the nitroacetaldehyde oxime is obtained through a Henry reaction under the action of alkali and is dehydrated under the action of thionyl chloride to obtain nitroacetonitrile; therefore, the efficient synthesis of nitroacetonitrile is achieved through two-step reaction, the requirement for temperature in the synthesis process is relatively wide, operation steps are not complex, and the method is suitable for industrial production. Thus, the product with stable yield and stable purity can be obtained, the production cost is low, the period is short, the problems of unstable yield and quality, high production cost, long production period and the like of a traditional preparation method are solved. Excellent technical support can be provided for subsequent application of nitroacetonitrile in the field of high-density energetic materials.

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

Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes

Drug resistance has become a major concern in the field of infection management, therefore searching for new antibacterial agents is getting more challenging. Our study presents an optimized and eco-friendly synthesis scheme for a panel of nitroalkenes be

Polyfunctional pyridines from nitroacetamidine and β-diketones. A useful synthesis of substituted imidazo[4,5-b]pyridines and related compounds

Nitroacetamidine undergoes a useful cyclocondensation with β-diketones to produce substituted 2-amino-3-nitropyridines. Use of an acylpyruvate generates hitherto unreported 2-amino-3-nitropyridine-4-carboxylates. These may be converted easily to functionalized imidazo[4,5-b]pyridines and oxazolo[5,4-b]pyridines.