3839-22-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Cyanobenzoic acid is used as a reactant in the synthesis of T-box riboswitch antiterminator RNA-binding oxazolidinone derivatives, which have potential applications in the development of new drugs targeting RNA-based regulatory mechanisms in various diseases.
Used in Chemical Industry:
2-Cyanobenzoic acid is used as a reactant in the synthesis of Benzoate modified β-cyclodextrin derivatives. These derivatives have potential applications in various fields, such as drug delivery, supramolecular chemistry, and the development of new materials with unique properties.
Used in Pharmaceutical Industry:
2-Cyanobenzoic acid is used as a reactant in the synthesis of Pyrrolo[1,2-f]triazines, which are potential JAK2 inhibitors. JAK2 inhibitors have potential applications in the treatment of various inflammatory and autoimmune diseases, as well as certain types of cancer.
Used in Chemical Industry:
2-Cyanobenzoic acid is used as a reactant involved in decarboxylation, decarboxylative halogenation, and protodecarboxylation reactions. These reactions are important in the synthesis of various organic compounds and the development of new chemical processes.
Used in Chemical Industry:
2-Cyanobenzoic acid may be used to synthesize phthalamidine, a compound with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H5NO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4H,(H,10,11)/p-1

Upstream product

• 601-70-7 3,3-dichlorophthalide 
• 169141-21-3 3,3-dibromo-phthalide 
• 445-69-2 phthaloyl fluoride 
• 6525-45-7 2-cyano-benzoic acid ethyl ester 
• 88-95-9 Phthaloyl dichloride 
• 6587-24-2 methyl 2-cyanobenzoate 
• 57-14-7 N,N-Dimethylhydrazine 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 17174-98-0 o-cyanobenzamide 
• 91-15-6 phthalonitrile 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 529-19-1 2-Methylbenzonitrile 

Downstream Products

• 88-99-3 benzene-1,2-dicarboxylic acid 
• 88-97-1 phthalamic acid 
• 27611-63-8 2-Cyanobenzoyl chloride 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 135689-93-9 4-(2-Cyanophenyl)benzaldehyde 
• 159589-69-2 4'-[(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]-2-cyanobenzanilide 
• 329083-19-4 1-acetyl-3-[1-hydroxy-1-(3-cyanophenyl)-methylidene]-5,6-dimethoxy-2-indolinone 
• 6587-24-2 methyl 2-cyanobenzoate 
• 1160509-17-0 2-cyanophenyl octyl sulfide 
• 1071849-95-0 potassium 2-cyanobenzoate 
• 1204331-33-8 N-{4-[1-(2-cyano-benzoyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-3-trifluoromethyl-benzoyl}-N'-(carbobenzyloxy)-guanidine 
• 1227610-00-5 2-(2-(4-cyclobutyl-1,4-diazepane-1-carbonyl)-7-azaspiro[3.5]nonane-7-carbonyl)benzonitrile 
• 100-02-7 4-nitro-phenol 
• 25832-66-0 o-cyanobenzoic acid, sodium salt 

Relevant academic research and scientific papers

Base mediated spirocyclization of quinazoline: One-step synthesis of spiro-isoindolinone dihydroquinazolinones

A novel approach for the spiro-isoindolinone dihydroquinazolinones has been demonstrated from 2-aminobenzamide and 2-cyanomethyl benzoate in the presence of KHMDS as a base to get moderate yields. The reaction has been screened in various bases followed by solvents and a gram scale reaction has also been executed under the given conditions. Based on the controlled experiments a plausible reaction mechanism has been proposed. Further the substrate scope of this reaction has also been studied.

Stepwise benzylic oxygenation via uranyl-photocatalysis

Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.

o-Cyanobenzoate: A Recyclable and Reusable Stereo-directing Group for β-O-Glycosylation via Pd(0)-catalyzed Ferrier Rearrangement

Inner sphere Tsuji-Trost reaction has found recent application for β-selective Ferrier rearrangement of glycal substrates with alcohol nucleophiles. Herein, we report an efficient and stereoselective synthesis of 2,3-dideoxy-β-O-glycosides from C3-(o-cyan

Photoinduced FeCl3-Catalyzed Alkyl Aromatics Oxidation toward Degradation of Polystyrene at Room Temperature?

While polystyrene is widely used in daily life as a synthetic plastic, the subsequently selective degradation is still very challenging and highly required. Herein, we disclose a highly practical and selective reaction for the catalytically efficient oxidation of alkyl aromatics (including 1°, 2°, and 3° alkyl aromatics) to carboxylic acids. While dioxygen was used as the sole terminal oxidant, this protocol was catalyzed by the inexpensive and readily available ferric compound (FeCl3) with irradiation of visible light (blue LEDs) under only 1 atmosphere of O2 at room temperature. This system could further facilitate the selective degradation of polystyrene to benzoic acid, providing an important and practical tool to generate high-value chemical from abundant polystyrene wastes.

Cleavage of Carboxylic Esters by Aluminum and Iodine

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

Methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted α-amino acids as promising building blocks in peptidomimetic synthesis: a comparative study

Abstract: An efficient and simple synthetic protocol for the synthesis of a number methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted (S)-α-amino acids via subsequent coupling and hydroxyamination of 2-cyanobenzamide derivatives has been developed. Comparative analysis of three pseudopeptide series based on 2-cyano- and 2-amidoxime-substituted benzoic acid and its pyridine and pyrazine counterparts has been provided and it has revealed a practical advantage of the benzoic acid derivatives due to their greater availability. The impact of the nitrogen atom in the aromatic ring on the trans/cis-amide equilibrium in the proline derivatives is discussed. Graphical abstract: [Figure not available: see fulltext.]

Pd-Catalyzed debenzylation and deallylation of ethers and esters with sodium hydride

Herein we demonstrate simply that the addition of Pd(OAc)2 as a promotor switches the reactivity of a commonly used base NaH to a nucleophilic reductant. The reactivity is engineered into a palladium-catalyzed reductive debenzylation and deallylation of aryl ethers and esters. This operationally simple, mild protocol displays a broad substrate scope and a broad spectrum of functional group tolerance (>50 examples) and high chemoselectivity toward aryl ethers over aliphatic structures. Moreover, the dual reactivity of NaH as a base and a reductant is demonstrated in efficient synthetic elaboration.

Application of metallide/palladium compound catalytic reduction system in debenzylation reaction and deuterization reaction

The invention discloses an application of a metallide/palladium compound catalytic reduction system in debenzylation reaction and deuterization reaction of benzyl-containing compounds. The reaction comprises the following steps: under the protection of nitrogen, suspending a palladium compound and a metallide in a solvent, stirring for 5 minutes, adding the benzyl-containing compounds, carrying out a reaction for 0.5 to 48 h at the temperature of -30 DEG C to 150 DEG C, adding ice water to stop the reaction, adjusting the pH value to 3.5 with diluted hydrochloric acid, extracting the reactionsolution by a solvent, drying by distillation, purifying by column chromatography, and thus completing the reaction.

Catalyst-free, efficient and one pot protocol for synthesis of nitriles from aldehydes using glycerol as green solvent

We described herein the novel, efficient and one-pot catalyst free protocol for the synthesis of nitriles from aldehydes by using hydroxyl amine hydrochlorides in glycerol as a green solvent. This protocol was efficiently used for transformation of aromatic aldehydes bearing electron-withdrawing and electron-donating groups into a aryl nitriles in good to excellent yields. The methodology offers a very simple, efficient and environmentally benign procedure.

NH4I/tert-butyl hydroperoxide-promoted oxidative C–N cleavage of tertiary amines leading to nitroaromatic compounds

A NH4I/tert-butyl hydroperoxide-promoted oxidation of tertiary N-aryl-N,N-dialkylamines in DMSO has been developed to access nitroaromatic compounds. This methodology involves sequential N-dealkylation reactions in one-pot and a radical pathway is proposed.