1878-71-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyanophenylacetic acid is used as a key intermediate in the synthesis of nonsteroidal anti-inflammatory drugs (NSAIDs) for its ability to provide anti-inflammatory and analgesic effects. It is also utilized in the production of other pharmaceutical compounds due to its versatile reactivity.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Cyanophenylacetic acid is employed as a precursor in the development of herbicides, contributing to the control of unwanted plant growth and enhancing crop productivity.
Used in Organic Chemistry:
3-Cyanophenylacetic acid is used as a reagent in various organic chemistry reactions, facilitating the synthesis of a wide range of organic compounds and aiding in the advancement of chemical research and development.
Used as a Precursor to Functionalized Acids and Esters:
3-Cyanophenylacetic acid serves as a precursor to other functionalized acids and esters, enabling the creation of diverse chemical entities with specific properties and applications across different industries.

InChI:InChI=1/C9H7NO2/c10-6-8-3-1-2-7(4-8)5-9(11)12/h1-4H,5H2,(H,11,12)

Upstream product

• 67-56-1 methanol 
• 143659-32-9 1-Naphthylmethyl 3-cyanophenylacetate 
• 52797-99-6 m-cyano-α-diazoacetophenone 
• 124-38-9 carbon dioxide 
• 1253037-56-7 m-cyanobenzyl methyl carbonate 
• 28188-41-2 m-(bromomethyl)benzonitrile 
• 16473-20-4 3-(Fluoromethyl)benzonitrile 
• 773837-37-9 sodium cyanide 
• 1878-69-9 3-iodophenylacetic acid 
• 14338-36-4 3-amino phenylacetic acid 
• 151-50-8 potassium cyanide 

Downstream Products

• 62043-92-9 4'-methoxy-α'-oxo-bibenzyl-3-carbonitrile 
• 62043-86-1 3-Cyanobenzyl-4'-methylphenylketon 
• 445003-61-2 methyl 2-(3-cyano-phenyl)-2-methyl-propionate 
• 178686-90-3 3-(4-pentylphenacyl) benzonitrile 
• 1097146-22-9 3-(3-oxo-4,5,6,7-tetrahydro-3H-isobenzofuran-1-ylidenemethyl)-benzonitrile 
• 210113-92-1 (3-aminomethyl-phenyl)-acetic acid ethyl ester hydrochloride 
• 1239437-24-1 3-(3-chloro-2-oxopropyl)benzonitrile 
• 52798-00-2 (3-cyano-phenyl)-acetic acid methyl ester 
• 1450927-39-5 tert-butyl 2-(3-cyanophenyl)acetate 

Relevant academic research and scientific papers

Visible-light photoredox-catalyzed selective carboxylation of C(sp3)?F bonds with CO2

It is highly attractive and challenging to utilize carbon dioxide (CO2), because of its inertness, as a nontoxic and sustainable C1 source in the synthesis of valuable compounds. Here, we report a novel selective carboxylation of C(sp3)?F bonds with CO2 via visible-light photoredox catalysis. A variety of mono-, di-, and trifluoroalkylarenes as well as α,α-difluorocarboxylic esters and amides undergo such reactions to give important aryl acetic acids and α-fluorocarboxylic acids, including several drugs and analogs, under mild conditions. Notably, mechanistic studies and DFT calculations demonstrate the dual role of CO2 as an electron carrier and electrophile during this transformation. The fluorinated substrates would undergo single-electron reduction by electron-rich CO2 radical anions, which are generated in situ from CO2 via sequential hydride-transfer reduction and hydrogen-atom-transfer processes. We anticipate our finding to be a starting point for more challenging CO2 utilization with inert substrates, including lignin and other biomass.

Suppressing carboxylate nucleophilicity with inorganic salts enables selective electrocarboxylation without sacrificial anodes

Although electrocarboxylation reactions use CO2as a renewable synthon and can incorporate renewable electricity as a driving force, the overall sustainability and practicality of this process is limited by the use of sacrificial anodes such as magnesium and aluminum. Replacing these anodes for the carboxylation of organic halides is not trivial because the cations produced from their oxidation inhibit a variety of undesired nucleophilic reactions that form esters, carbonates, and alcohols. Herein, a strategy to maintain selectivity without a sacrificial anode is developed by adding a salt with an inorganic cation that blocks nucleophilic reactions. Using anhydrous MgBr2as a low-cost, soluble source of Mg2+cations, carboxylation of a variety of aliphatic, benzylic, and aromatic halides was achieved with moderate to good (34-78%) yields without a sacrificial anode. Moreover, the yields from the sacrificial-anode-free process were often comparable or better than those from a traditional sacrificial-anode process. Examining a wide variety of substrates shows a correlation between known nucleophilic susceptibilities of carbon-halide bonds and selectivity loss in the absence of a Mg2+source. The carboxylate anion product was also discovered to mitigate cathodic passivation by insoluble carbonates produced as byproducts from concomitant CO2reduction to CO, although this protection can eventually become insufficient when sacrificial anodes are used. These results are a key step toward sustainable and practical carboxylation by providing an electrolyte design guideline to obviate the need for sacrificial anodes.

Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2

The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2 to generate important aryl acetic acids is reported. Besides aldehyde hydrazones, a variety of ketone hydrazones, which have not been successfully applied in previous umpolung reactions with other reactive electrophiles, also show high reactivity and selectivity under mild conditions. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and offers easy derivation of important structures, including bioactive felbinac and adiphenine. Computational studies reveal that this umpolung reaction proceeds through the generation of a Ru-nitrenoid followed by concerted [4 + 2] cycloaddition with CO2.

Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic Halides at Room Temperature

The first photoinduced copper(I)-catalyzed cyanation of aromatic halides at room temperature has been developed. The sp2 cyanation reaction exhibits outstanding tolerance to functional groups including primary amines and carboxylic acids, and chemoselectivity to SN2-reactive alkyl chlorides. Mechanistic investigations indicate that the reaction occurs via a single-electron transfer (SET) between the aryl halide and an excited copper(I) cyanide catalytic intermediate. (Figure presented.).

Electrochemical carboxylation of benzylic carbonates: Alternative method for efficient synthesis of arylacetic acids

Electrochemical carboxylation of benzylic carbonates was successfully performed as an alternative method for the synthesis of phenylacetic acids by using a one-compartment cell equipped with a Pt plate cathode and an Mg rod anode in CH3CN to afford the corresponding phenylacetic acids in good yields.

N-SULFONYL THIAZOLYLPIPERAZINE DERIVATIVES AND RELATED N-SULFONYL HETEROCYCLIC DERIVATIVES FOR THE TREATMENT OF NEURO DEGENERATIVE DISEASES

This invention provides thiazolylpiperazine derivatives, and N-sulfonyl heterocyclic derivatives including phenyl- and benzyl-thiazolylpiperidine derivatives, and pharmaceutically acceptable salts thereof, which are useful active ingredients for administration in a method for the treatment of an α-synucleopathy such as Parkinson's disease, diffuse Lewy body disease, traumatic brain injury, amyotrophic lateral sclerosis, Niemann-Pick disease, Hallervorden-Spatz syndrome, Down syndrome, neuroaxonal dystrophy, multiple system atrophy and Alzheimer's disease. This invention also provides methods for making such derivatives, and pharmaceutical compositions including such derivatives together with pharmaceutically acceptable excipients.

Photolysis of the 1-naphthylmethyl ester of substituted phenylacetic acids: intramolecular charge transfer and rates of decarboxylation of arylacyl radicals

The photolysis of esters 6 and 8 in methanol leads to products resulting from both naphthylmethyl cations and radicals.The product distribution is nearly independent of X for the esters 6 except when X equals methoxy.A mechanism involving initial homolytic cleavage of the carbon-oxygen bond in the excited singlet state of the ester is proposed.Competition between electron transfer in the radical pair to form the ion pair and decarboxylation of the arylacyloxy radical allows calculations of the rates of this decarboxylation process.The ρ values versus ? is close to zero.When X equals methoxy, intramolecular electron transfer occurs with the naphthalene ring serving as the acceptor and the methoxyaromatic as the donor.This exciplex fragments to carbon dioxide and 1-(1-naphthyl)-2-arylethane. Key words: acyloxy radical, decarboxylation, photolysis of benzylic esters.