610-66-2

Basic information

• Product Name: 2-Nitrophenylacetonitrile
• Synonyms: (o-nitrophenyl)-acetonitril;2-nitro-benzeneacetonitril;2-nitrobenzeneacetonitrile;2-nitrobenzylnitrile;o-nitrobenzacetonitrile;O-NITROBENZYL CYANIDE;2-NITROBENZYL CYANIDE;2-NITROPHENYLACETONITRILE
• CAS NO: 610-66-2
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• EINECS: 210-231-0
• Product Categories: benzene derivative;Aromatic Nitriles;Aromatics;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C8 to C9;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 610-66-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: 82-85 °C(lit.)
• Boiling Point: 178°C
• Flash Point: 138 °C
• Appearance: Light brown to brownish-gray/Powder
• Density: 1.3264 (rough estimate)
• Vapor Pressure: 0.000864mmHg at 25°C
• Refractive Index: 1.5770 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate
• Water Solubility: <0.01 g/100 mL at 20℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 1869400
• CAS DataBase Reference: 2-Nitrophenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrophenylacetonitrile(610-66-2)
• EPA Substance Registry System: 2-Nitrophenylacetonitrile(610-66-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: 3439
• WGK Germany: 3
• RTECS: AM1248000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 610-66-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

2-Nitrophenylacetonitrile was used in synthesis of 2 or 2,4-substituted α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones. It was used in the synthesis of strychnine.

Synthesis Reference(s)

Synthesis, p. 514, 1987 DOI: 10.1055/s-1987-27989

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitriles, such as 2-Nitrophenylacetonitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Fire Hazard

Flash point data for 2-Nitrophenylacetonitrile are not available. 2-Nitrophenylacetonitrile is probably combustible.

InChI:InChI=1/C8H6N2O2/c9-6-5-7-3-1-2-4-8(7)10(11)12/h1-4H,5H2

Upstream product

• 140-29-4 phenylacetonitrile 
• 151-50-8 potassium cyanide 
• 612-23-7 2-nitrobenzyl chloride 
• 107-14-2 chloroacetonitrile 
• 98-95-3 nitrobenzene 
• 35120-10-6 methylthioacetonitrile 
• 61540-35-0 S-(Dimethylthiocarbamoyl)thioglycolonitrile 
• 5219-61-4 (phenylthio)acetonitrile 
• 3598-14-9 phenoxyacetonitrile 
• 7697-37-2 nitric acid 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 3156-39-6 (E)-1-nitro-2-(2-nitrovinyl)benzene 
• 612-25-9 2-Nitrobenzyl alcohol 

Downstream Products

• 112181-38-1 2,3-Bis(2-nitrophenyl)propanenitrile 
• 873978-95-1 2,4-dihydroxy-2'-nitro-deoxybenzoin 
• 136764-93-7 2-Ethyl-2-(2-nitro-phenyl)-butyronitrile 
• 147644-06-2 1-(2-nitrophenyl)cyclopropane-1-carbonitrile 
• 136764-94-8 2-Allyl-2-(2-nitro-phenyl)-pent-4-enenitrile 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 1969-74-0 2-phenylisatogen 
• 91477-03-1 3-phenyl-4-o-nitrophenyl-isoxazole 
• 96129-47-4 4-(2-Nitro-phenyl)-isoxazole-3-carboxylic acid ethyl ester 
• 14714-50-2 2-hydroxybenzyl cyanide 
• 88975-25-1 2-(2-(methylamino)phenyl)acetonitrile 
• 88975-95-5 (2-Cyanato-phenyl)-acetonitrile 
• 88975-36-4 N-(2-Cyanomethyl-phenyl)-2,2,2-trifluoro-acetamide 
• 88975-64-8 [2-(Thiazol-2-ylamino)-phenyl]-acetic acid 

Relevant articles and documents

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Substituted conformationally restricted guanidine derivatives: Probing the α2-adrenoceptors’ binding pocket

In this paper we report the design, synthesis and pharmacological evaluation of new N-substituted 2-amino-1,4-dihydroquinazolines, 2-amino-1,4-dihydropyridopyrimidines and 2-amino-4,5-dihydro-1,3-benzodiazepines as α2-adrenoceptors ligands. Computational studies show that the proposed substitutions and guanidine-containing ring size will probe an extensive area of the active site. Preparation of these molecules involved novel routes than those previously utilised in our laboratory for the preparation of the acyclic aryl-guanidine counterparts. Compounds 8b and 18c showed the highest affinity and antagonistic activity, within their series, towards the α2-adrenoceptor in human brain tissue in?vitro experiments. Structure-activity relationships have been established for the design and biological evaluation of novel α2-adrenoceptor ligands.

A heterogeneous palladium catalyst hybridised with a titanium dioxide photocatalyst for direct C-C bond formation between an aromatic ring and acetonitrile

A palladium catalyst hybridised with a titanium dioxide photocatalyst can promote cyanomethylation of an aromatic ring by using acetonitrile, where the photocatalyst activates acetonitrile to form a cyanomethyl radical before the C-C bond formation using the palladium catalyst.