10406-24-3

Usage

Uses

Used in Pharmaceutical Industry:
3-CYANOBENZYLAMINE is used as a key intermediate for the preparation of indole and indazole derivatives, which are known for their potential as orexin receptor antagonists. These antagonists play a significant role in the development of medications targeting various conditions, such as insomnia, addiction, and other disorders related to the central nervous system.

InChI:InChI=1/C8H8N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5,9H2

Upstream product

• 62898-68-4 α-phthalimido-m-tolunitrile 
• 90390-50-4 1-(3-Cyano-benzyl)-3,5,7-triaza-1-azonia-tricyclo[3.3.1.1^3,7]decane; bromide 
• 626-17-5 benzene-1,3-dicarbonitrile 
• 1156122-53-0 2-{[(3-cyanophenyl)methyl]carbamoyl}benzoic acid 
• 49584-07-8 3-cyanophenyl-4-methylbenzene-1-sulfonate 
• 873-62-1 m-cyanophenol 
• 766-84-7 3-chloro-benzonitrile 
• 1235553-97-5 naphthalen-2-yl 4-methylbenzene-1-sulfonate 
• 916213-93-9 tert-butyl (3-cyanobenzyl)carbamate 
• 220324-83-4 2-[(3-cyanophenyl)methyl]imidodicarbonic acid 1,3-bis(1,1-dimethylethyl) ester 
• 7664-41-7 ammonia 
• 108-38-3 m-xylene 
• 28188-41-2 m-(bromomethyl)benzonitrile 
• 328552-90-5 3-(azidomethyl)benzonitrile 

Downstream Products

• 1477-55-0 1,3-di(aminomethyl)benzene 
• 1313039-62-1 3-((5-methyl[1,2,4]triazin-3-ylamino)methyl)benzonitrile 
• 28188-41-2 m-(bromomethyl)benzonitrile 
• 874-97-5 3-(hydroxymethyl)benzonitrile 
• 1877-72-1 3-Cyanobenzoic acid 
• 133671-96-2 α-(p-toluenesulfonamido)-m-tolualdehyde 

Relevant academic research and scientific papers

An efficient hydrogenation of dinitrile to aminonitrile in supercritical carbon dioxide

The highly selective hydrogenation of adiponitrile proceeds effectively in supercritical carbon dioxide (scCO2) to produce 6-aminocapronitrile with excellent selectivity of 100% over rhodium/alumina (Rh/Al2O 3) and without any additive, which is impossible in classical organic solvents. The presence of CO2 can be beneficial or mandatory for the exclusive formation of the aminonitrile as it can act as a solvent to enhance the activity and also as temporary protecting agent to increase the selectivity. These results successfully show the general concept of using scCO2 as a protective medium for the selectivity control of dinitrile to aminonitrile reactions. Recycling of the catalyst and further extension of this method to other dinitriles were also investigated.

Site-specific enzymatic introduction of a norbornene modified unnatural base into RNA and application in post-transcriptional labeling

Inverse electron demand Diels-Alder cycloadditions have proven to be extremely useful for mild and additive-free orthogonal labeling of biomolecules, amongst others, for RNA labeling in vitro and in a cellular context. Here we present a method for site-specific introduction of an alkene modification into RNA via T7 in vitro transcription. For this, an unnatural, hydrophobic base pairing system developed by Romesberg and coworkers was modified introducing one or two norbornene moieties at predefined positions into RNA oligonucleotides in an in vitro transcription reaction. This allows post-transcriptional functionalization of these RNA molecules with tetrazine derivatives containing for instance fluorophores or biotin.

2-IMIDAZOLYL-PYRIMIDINE SCAFFOLDS AS POTENT AND SELECTIVE INHIBITORS OF NEURONAL NITRIC OXIDE SYNTHASE

Imidazolyl-pyrimidine and related compounds, as can utilize heme-iron coordination in the selective inhibition of neuronal nitric oxide synthase.

Novel 2,4-disubstituted pyrimidines as potent, selective, and cell-permeable inhibitors of neuronal nitric oxide synthase

Selective inhibition of neuronal nitric oxide synthase (nNOS) is an important therapeutic approach to target neurodegenerative disorders. However, the majority of the nNOS inhibitors developed are arginine mimetics and, therefore, suffer from poor bioavai

Photostimulated reduction of nitriles by SmI2

Despite their high electron-withdrawing strength, nitriles are not good electron acceptors and therefore are hard to reduce. In this work, using photostimulation in the visible region, we examined the reactivity of aliphatic and aromatic, mono- and dicyano compounds in reaction with SmI2. A proton donor that complexes efficiently with SmI2 must be used. Maximum yield was obtained at ca.0.2 M MeOH. Aromatic nitriles were more reactive than aliphatic nitriles, which exhibited negligible yields. Phenylacetonitrile presents an intermediate reactivity. The mechanism of the reaction involves coordination of the SmI2 to the lone pair of the nitrile nitrogen followed by an inner sphere electron transfer. Surprisingly, m-dicyanobenzene was less reactive than the monocyano derivative benzonitrile. This was traced to the lower ability of the dicyano compound to coordinate to the SmI2 due to, as was shown by quantum mechanical calculations, its lone pair having an energy significantly lower than that of benzonitrile. It is noteworthy that at the SmI2 initial concentration used (0.04M), light penetrates only the 0.4 mm outer layer of the reaction mixture. Therefore the photostimulation effect observed was due to irradiation of only 4% of the total reaction volume, implying that under optimal conditions the effect should be 25 times larger.

One-pot primary aminomethylation of aryl and heteroaryl halides with sodium phthalimidomethyltrifluoroborate

A one-pot primary aminomethylation of aryl halides, triflates, mesylates, and tosylates via Suzuki-Miyaura cross-coupling reactions with sodium phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine is reported.

PROCESS FOR PRODUCING XYLYLENEDIAMINE

The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass% or less and a xylylenediamine content of 1 mass% or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.

(3-HYDROXY-4-AMINO-BUTAN-2-YL) -3- (2-THIAZOL-2-YL-PYRROLIDINE-1-CARBONYL) BENZAMIDE DERIVATIVES AND RELATED COMPOUNDS AS BETA-SECRETASE INHIBITORS FOR TREATING

The present invention provides novel beta-secretase inhibitors and methods for their use, including methods of treating of Alzheimer's disease. (Formula)

PRODUCTION METHOD OF PRIMARY AMINES AND CATALYSTS FOR PRODUCING PRIMARY AMINES

A method of producing a primary amine by the hydrogenation of a nitrile in the presence of a hydrogenation catalyst. The hydrogenation catalyst contains at least one metal selected from the group consisting of nickel, cobalt and iron. Before use in the hydrogenation of nitrile, the hydrogenation catalyst is pretreated with at least one treating agent selected from the group consisting of hydrocarbons, alcohols, ethers, esters and carbon monoxide at 150 to 500° C.

Production of Xylylenediamines

A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.