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

Uses

Used in Pharmaceutical Industry:
2-Nitrophenylacetonitrile is used as a synthetic intermediate for the production of 2 or 2,4-substituted α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones. These α-carbolines have potential applications in the pharmaceutical industry due to their diverse biological activities.
Used in Organic Synthesis:
2-Nitrophenylacetonitrile is also used in the synthesis of strychnine, a highly toxic alkaloid with potential applications in medicine and research. Its use in organic synthesis allows for the creation of various complex organic molecules with specific properties and functions.

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

• 27878-36-0 2-hydroxyimino-3-(2-nitro-phenyl)-propionic acid 
• 861560-54-5 nitro-phenyl-acetic acid amide 
• 108-24-7 acetic anhydride 
• 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 
• 143-33-9 sodium cyanide 
• 3958-60-9 2-nitrophenylmethyl bromide 

Downstream Products

• 120-72-9 indole 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 2973-50-4 2-aminophenylacetonitrile 
• 112181-38-1 2,3-Bis(2-nitrophenyl)propanenitrile 
• 873978-95-1 2,4-dihydroxy-2'-nitro-deoxybenzoin 
• 86162-68-7 (2-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-phenyl)-acetonitrile 
• 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 
• 96129-38-3 5-Amino-4-(2-nitro-phenyl)-isoxazole-3-carboxylic acid ethyl ester 
• 96129-37-2 4-(2-Nitro-phenyl)-3-phenyl-isoxazol-5-ylamine 
• 14714-50-2 2-hydroxybenzyl cyanide 
• 88975-25-1 2-(2-(methylamino)phenyl)acetonitrile 
• 88975-95-5 (2-Cyanato-phenyl)-acetonitrile 

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

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

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.

An efficient and practical synthesis of [2-11C]indole via superfast nucleophilic [11C]cyanation and RANEY Nickel catalyzed reductive cyclization

A rapid method for the synthesis of carbon-11 radiolabeled indole was developed using a sub-nanomolar quantity of no-carrier-added [11C]cyanide as radio-precursor. Based upon a reported synthesis of 2-(2-nitrophenyl)acetonitrile (2), a highly reactive substrate 2-nitrobenzyl bromide (1) was evaluated for nucleophilic [11C]cyanation. Additionally, related reaction conditions were explored with the goal of obtaining of highly reactive 2-(2-nitrophenyl)-[1-11C]acetonitrile ([11C]-2) while inhibiting its rapid conversion to 2,3-bis(2-nitrophenyl)-[1-11C]propanenitrile ([11C]-3). Next, a RANEY Nickel catalyzed reductive cyclization method was utilized for synthesizing the desired [2-11C]indole with hydrazinium monoformate as the active reducing agent. Extensive and iterative screening of basicity, temperature and stoichiometry was required to overcome the large stoichiometry bias that favored 2-nitrobenzylbromide (1) over [11C]cyanide, which both caused further alkylation of the desired nitrile and poisoned the RANEY Nickel catalyst. The result is an efficient two-step, streamlined method to reliably synthesize [2-11C]indole with an entire radiochemical yield of 21 ± 2.2% (n = 5, ranging from 18-24%). The radiochemical purity of the final product was >98% and specific activity was 176 ± 24.8 GBq μmol-1 (n = 5, ranging from 141-204 GBq μmol-1). The total radiosynthesis time including product purification by semi-preparative HPLC was 50-55 min from end of cyclotron bombardment.

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.

Syntheses of two isotopically labeled CB1 receptor antagonists

Synthesis of deuterium-labeled CB1 receptor antagonist 2-d 9 was accomplished in three steps by alkylation of 2-nitrophenylacetonitrile with cyclopentyl-d9 bromide, reductive cyclization of the resulting secondary nitrile into the 3-cyclopentyl indole-d9 and its N-sulfonylation with corresponding p-amidosulfonyl chloride. Another, structurally related, CB1 receptor antagonist 1 was radiolabeled with carbon-14 by oxidative cleavage of 3-cyclopentyl indole followed by the ring closure of o-acyl substituted N-formylaniline with potassium cyanide-[14C], in situ reduction-elimination of the intermediate amino alcohol, and N-sulfonylation of the resulting 3-cyclopentyl indole-2-[14C]. Copyright

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration

Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf 2O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf2O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K T/KB = 5-10) in (Figure presented) between values reported for covalent nitrates and preformed nitronium salts.

Efficient methods for the synthesis of arylacetonitriles

Various approaches to [2-fluoro-4-(trifluoromethyl)phenyl]acetonitrile were investigated. Two of these methods were selected and applied to a variety of electron-deficient substrates, thereby expanding the scopes of the procedures.

Synthesis, analgesic and anti-inflammatory activities of novel 3-(4-acetamido-benzyl)-5-substituted-1,2,4-oxadiazoles

A series of 3-(4-acetamido-benzyl)-5-substituted-1,2,4-oxadiazoles (7a-7n) were synthesized and screened for analgesic and in vivo anti-inflammatory activities using acetic acid writhing in mice model and carrageenan-induced paw oedema method in mice, respectively. The analgesic activity of compounds 7i and 7m is superior while that of 7d, 7c, 7f and 7j is equal to the reference standard, diclofenac sodium. The anti-inflammatory activity of compounds 6, 7c, 7e, 7f, 7i, 7l, 7m and 7n is found to be superior than that of diclofenac sodium which is used as a reference, while compounds 7d and 7g are found to be equipotent with the reference compound.

Synthesis of 3,5-disubstituted [1,2,4]-oxadiazoles

Substituted amidoximes have been synthesized, and converted to corresponding oxadiazoles as a novel heterocyclic compounds under mild conditions in good to excellent yield.