610-66-2 Usage
Description
2-Nitrophenylacetonitrile is an organic compound that is classified as a nitro compound and a nitriles. It is a yellow solid and is primarily used as a synthetic intermediate in the production of various organic compounds.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 610-66-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 0 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 610-66:
(5*6)+(4*1)+(3*0)+(2*6)+(1*6)=52
52 % 10 = 2
So 610-66-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H6N2O2/c9-6-5-7-3-1-2-4-8(7)10(11)12/h1-4H,5H2
610-66-2Relevant articles and documents
Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes
Hu, Dandan,Liu, Jiayue,Ren, Hongjun,Song, Jinyu,Zhang, Jun-Qi,Zhu, Guorong
supporting information, p. 786 - 790 (2022/01/28)
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
McMullan, Michela,García-Bea, Aintzane,Miranda-Azpiazu, Patricia,Callado, Luis F.,Rozas, Isabel
, p. 48 - 57 (2016/08/01)
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
Yoshida, Hisao,Fujimura, Yuki,Yuzawa, Hayato,Kumagai, Jun,Yoshida, Tomoko
supporting information, p. 3793 - 3795 (2013/05/22)
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.
