72301-65-6

Usage

Uses

Used in Pharmaceutical Industry:
2-(5-Chloro-2-nitrophenyl)acetonitrile is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, 2-(5-Chloro-2-nitrophenyl)acetonitrile is used as an intermediate in the production of pesticides and other agrochemicals. Its reactivity and chemical properties make it a valuable component in the development of effective and targeted pest control solutions.
Used in Organic Synthesis:
2-(5-Chloro-2-nitrophenyl)acetonitrile is utilized in organic synthesis for the preparation of various organic compounds. Its versatility and reactivity make it a valuable building block in the synthesis of complex organic molecules for a wide range of applications.

InChI:InChI=1/C8H5ClN2O2/c9-7-1-2-8(11(12)13)6(5-7)3-4-10/h1-2,5H,3H2

Upstream product

• 61540-35-0 S-(Dimethylthiocarbamoyl)thioglycolonitrile 
• 100-00-5 4-chlorobenzonitrile 
• 5219-61-4 (phenylthio)acetonitrile 
• 75-05-8 acetonitrile 
• 82272-28-4 cyanomethylenetrimethylammonium iodide 
• 3598-13-8 (4-chlorophenoxy)acetonitrile 
• 107-14-2 chloroacetonitrile 

Downstream Products

• 189696-91-1 2-(5-Chloro-2-nitro-phenyl)-3-(3,4-dichloro-phenyl)-propionitrile 
• 22908-28-7 (5-chloro-2-nitro-phenyl)-acetic acid 
• 332150-64-8 2-(5-chloro-2-nitro-phenyl)-1-(2,4-dihydroxy-phenyl)-ethanone 
• 332150-63-7 3-(5-chloro-2-nitro-phenyl)-7-hydroxy-chromen-4-one 
• 1259405-80-5 (5-chloro-2-nitrophenyl)(1-methylpyrrolidin-2-ylidene)acetonitrile 
• 1352276-48-2 2-(5-chloro-2-nitrophenyl)-3-pyrrolidin-1-ylpent-2-enenitrile 
• 153887-96-8 (E)-2-(5-Chloro-2-nitro-phenyl)-5-phenyl-pent-4-enenitrile 

Relevant academic research and scientific papers

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.

Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co-Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions

A cobalt-rhodium heterobimetallic nanoparticle-catalyzed reductive cyclization of 2-(2-nitroaryl)acetonitriles to indoles has been achieved. The tandem reaction proceeds without any additives under the mild conditions (1 atm H2 and 25 °C). This procedure could be scaled up to the gram scale. The catalytic system is significantly stable under these reaction conditions and could be reused more than ten times without loss of catalytic activity.

Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives

We report on a novel synthesis towards benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives by using ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole-4-carboxylic acid methylester moiety was produced. Refluxing the ortho-methoxy series in HBr/HAc produced the desired benzofuran-2-yl-methanamines. Accordingly, for the synthesis of indoles the nitro-group was first reduced and refluxing these intermediates in HCl gave the corresponding indol-2-yl-methanamines. The method worked well with electron donating substituents. Limitations regarding electron withdrawing substituents are discussed. This straightforward synthetic procedure can be a useful approach to generate a variety of substituted benzofuran-2-yl-methanamine and indol-2-yl-methanamine compounds by starting from readily available phenylacetic acid derivatives.

Short and simple method of synthesis of some pyrrolo[3,2-b]quinoline derivatives from easily available nitrobenzene derivatives

The Vilsmeier-Hack condensation of ortho-cyanomethylated nitroarenes with N-methylpyrrolidone, followed by cyclization promoted by O,N- bistrimethylsilylacetamide and DBU in DMF led directly to pyrrolo[3,2-b] quinoline derivatives. Georg Thieme Verlag Stuttgart · New York.

An aminoisoflavone-salicyloylindole ring transformation

A series of 2′-nitroisoflavones 8-10, 15, 22, 27 and 28 was prepared via the (2-nitro-phenyl)-acetic acids 1, 13, 19 and 25. In order to obtain the corresponding 2′-aminoisoflavones the reduction of 8-10, 15, 22, 27 and 28 was undertaken. Surprisingly, new 3-salicyloylindoles instead of the expected 2′-aminoisoflavones were the main reduction products. In the following paper the preparation of the 2′-nitroisoflavones 8-10, 15, 22, 27 and 28 as well as the reduction experiments obtaining the 2′-aminoisoflavones 33 and 35 and the 3-salicyloylindoles 29-32, 34 and 36 will be described. Furthermore, a possible mechanism responsible for the formation of the 3-salicyloylindoles from 2′-nitroisoflavones under reductive conditions will be discussed.

Hypoglycemic imidazoline compounds

This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.

Base-mediated reaction of quaternary ammonium salts with nitroarenes - Their useful functionalization via vicarious nucleophilic substitution (VNS)

Ammonium ylides generated from ammonium salt 1a-e with a base react with derivatives of 3-nitropyridine 2a-c and 2-nitrothiophene (3) to form products of vicarious nucleophilic substitution (VNS) 7, 8, or 9 respectively. The products of VNS 10, 11, or 12 are also produced from the corresponding ammonium salts, a base and 4-chloro-nitrobenzene (4), nitrobenzene (5), or 1-nitronaphthalene (6), respectively. In a few products, an exchange of alkoxy group 7c or substitution of chlorine by alkoxyl 8a,b occured.

Specific ortho-Cyanomethylation of Nitroarenes via the Vicarious Nucleophilic Substitution of Hydrogen

The vicarious nucleophilic substitution of hydrogen in nitroarenes with acetonitrile derivatives XCH2CN in t-BuOK/THF base/solvent system proceeds exclusively ortho to the nitro group.Strong influence of substituents Z in 3-Z-nitrobenzene derivatives on the orientation has been observed.

Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with α-Substituted Nitriles and Esters. Direct α-Cyanoalkylation and α-Carbalkoxyalkylation of Nitroarenes

Carbanions generated from alkanenitriles bearing α-chloro, α-OR, or α-SR groups and from aliphatic esters bearing α-SR groups react with mononitroarenes to replace hydrogen atoms of the nitroaromatic ring ortho or para to the nitro group with α-cyanoalkyl or α-carbalkoxyalkyl substituents.The nucleophilic replacement of hydrogen with such carbanions proceeds faster than substitution of halogen ortho or para to the nitro group.

NUCLEOPHILIC SUBSTITUTION OF 4-CHLOROQUINOLINE 1-OXIDE AND RELATED COMPOUNDS BY MEANS OF HYDRIDE ELIMINATION

The reaction of 4-chloroquinoline 1-oxide (1) with pinacolone and t-BuOK in t-BuNH2 at -10 ca. -15 deg C gives 4-chloro-2-pinacolylquinoline 1-oxide in good yield by means of hydride-elimination.Similar reactions of 1 with acetone, 2-butanone, acetophenone, and ethyl and t-butyl acetates occur when treated with t-BuOK or n-BuLi in t-BuNH2 at -10 ca. -15 deg C, or t-BuOK, KNH2 or NaNH2 in liq NH3 at -70 deg C.Reactions of this type proceed also with quinoline 1-oxide (2), 3-bromoquinoline 1-oxide (3), p-chloronitrobenzene (4) and nitrobenzene.