16011-90-8

Usage

Uses

Used in Pharmaceutical Industry:
4-aminobutyronitrile monohydrochloride is used as a key intermediate for the production of various drugs, particularly for the treatment of diseases such as cancer and hypertension.
Used in Agrochemical Industry:
4-aminobutyronitrile monohydrochloride is used as a building block in the synthesis of pesticides and other agricultural chemicals, contributing to the development of effective and sustainable solutions for crop protection.
Used in Chemical Industry:
4-aminobutyronitrile monohydrochloride is used as an important component in the manufacture of a wide range of products, highlighting its value and significance in the chemical industry.

InChI:InChI=1/C4H8N2.ClH/c5-3-1-2-4-6;/h1-3,5H2;1H

Upstream product

• 146952-04-7 5-Amino-2-(hydroxyimino)pentansaeure 
• 5332-06-9 4-bromobutanenitrile 
• 110-61-2 butanedinitrile 
• 32754-99-7 4-aminobutyronitrile 

Downstream Products

• 32039-00-2 4-(Benzoylamino)butansaeurenitril 
• 150671-79-7 4-(Phenylacetylamino)butansaeurenitril 

Relevant academic research and scientific papers

An improved synthesis of 4-aminobutanenitrile from 4-azidobutanenitrile and comments on room temperature stability

4-Aminobutanenitrile (1) is an important synthetic intermediate for neurological disorder therapeutics including Parkinson’s and Alzheimer’s diseases, and is an industrial precursor to pyrroline and pyrrolidine. Synthesis of 1 by Co(II) catalyzed reduction of 4-azidobutanenitrile (2) with NaBH4, or by a one-pot Staudinger reduction of 2 in THF, was low yielding. 1H-NMR analysis of the Staudinger reduction revealed the formation of iminophosphorane intermediate (3) after 22 h at rt, and that increasing the reaction temperature from rt to 40 °C promoted hydrolysis of 3 to 1. A modified Staudinger reduction of 2 involving pyridine as solvent, addition of water 3 h after triphenylphosphine, and a temperature increase to 40 °C, gave rise to 1 in 69% yield. 1 is unstable at rt, thus the hydrochloride salt of 1 (1?HCl) was prepared by bubbling HCl(g) through a solution of 1 in chloroform. 1?HCl is stable at rt and is hence the preferred form for storage.

Copper-catalyzed ring-opening C(sp3)-N coupling of cycloketone oxime esters: Access to 1°, 2° and 3° alkyl amines

A novel copper-catalyzed C(sp3)-N coupling of cycloketone oxime esters with nitrogen nucleophiles has been realized. All of the N-aryl/alkylanilines, anilines and benzophenone imine could be employed in this protocol to produce a variety of 1°, 2° and 3° alkyl amines in one or two steps. These resultant cyano-containing alkyl amines were proven to be versatile synthetic building blocks in a variety of chemical transformations.

Straightforward access to cyclic amines by dinitriles reduction

1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.

Novel aromatic compounds and poly(oxyalkylene) containing aromatic compounds possessing antibacterial, antifungal or antitumor activity

The present invention provides novel compounds possessing one or more of the following activities: antibacterial, antifungal and antitumor activity. The compounds are of Formula (I): Pharmaceutical compositions containing these compounds, methods of making and methods for using these compounds are also provided.

Novel compounds possessing antibacterial, antifungal or antitumor activity

The present invention provides novel compounds possessing one or more of the following activities: antibacterial, antifungal and antitumor activity. The compounds are of Formula (I): Pharmaceutical compositions containing these compounds, methods of making and methods for using these compounds are also provided.

Ring-Opening Reactions of 1,2-Didehydroprolines, I. - Synthesis of 4-Hydroxyornithine and Protected 4-Amino-3-hydroxybutyronitriles

The cyclic azomethines 6a, b, d and f easily undergo ring-opening reaction with hydroxylamine and its O-alkyl derivatives leading to the oximino compounds 3a, b, d and f-i.Dissolved alkali metals in amines (Birch conditions) give satisfactory yields of reduction products with a stereochemistry depending on the substitution pattern in 3b, d, f-i.In case of 3d, the (2R,4R) stereoisomer 9b is the sole product, which can subsequently be cleaved to give 8b.Compounds 3g-i give predominantly the (2S,4R) product 8a.Acylation under alkaline conditions decarboxylates the oximino compounds 3b and d to the corresponding protected butyronitriles 14a-h.Trifluoroacetic anhydride tranforms 3b into the nitrile 14i together with the cyclization product 15.Key Words: 1,2-Didehydroprolines / Oxime reduction / Ornithine derivatives / Butyronitriles / 2-Piperidones / Proline derivatives / Amino acids