39201-33-7

Usage

Uses

Used in Chemical Synthesis:
4-Cyanobutyric acid is used as a key intermediate in the synthesis of various organic compounds, particularly in the production of lactams from aliphatic α,ω-dinitriles. Lactams are important building blocks for the synthesis of biodegradable polymers, pharmaceuticals, and other specialty chemicals.
Used in Chemoenzymic Production:
4-Cyanobutyric acid plays a crucial role in chemoenzymic processes, which combine chemical and enzymatic reactions to produce complex molecules with high selectivity and efficiency. This application takes advantage of the compound's ability to participate in various chemical transformations, making it a valuable asset in the development of sustainable and environmentally friendly synthetic methods.

InChI:InChI=1/C5H7NO2/c6-4-2-1-3-5(7)8/h1-3H2,(H,7,8)

Upstream product

• 5699-72-9 1-Cyanobutanol 
• 544-13-8 Glutaronitrile 

Downstream Products

• 41126-15-2 methyl 4-cyanobutanoate 
• 1121-89-7 piperidine-2,6-dione 
• 110-94-1 1,5-pentanedioic acid 
• 629-40-3 octanedinitrile 
• 26823-02-9 5-(4-methoxyphenyl)-5-oxopentanenitrile 
• 61718-86-3 5-oxo-5-[4-(trifluoromethyl)phenyl]pentanenitrile 
• 25917-55-9 4-cyano-N-phenylbutanamide 
• 53897-27-1 4-cyanobutanamide 

Relevant academic research and scientific papers

Preparation of lactams from aliphatic α, ω-dinitriles

A process for the preparation of five-membered or six-membered ring lactams from aliphatic α,ω-dinitriles has been developed. In the process an aliphatic α,ω-dinitrile is first converted to an ammonium salt of an ω-nitrile-carboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and arnidase (EC 3.5.1.4) activities. The ammonium salt of the ω-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate ω-nitrilecarboxylic acid or ω-aminocarboxylic acid. When the aliphatic α,ω-dinitrile is also unsymmetrically substituted at the α-carbon atom, the nitrilase produces the ω-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the ω-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

SELECTIVE HYDROLYSIS OF NITRILES UNDER MILD CONDITIONS BY AN ENZYME

A wide range of aromatic/aliphatic nitriles and dinitriles have been selcetively hydrolysed using a commercially available enzyme preparation from a Rhodococcuc sp.

BACTERIA IN ORGANIC SYNTHESIS: SELECTIVE CONVERSION OF 1,3-DICYANOBENZENE INTO 3-CYANOBENZOIC ACID

Suspensions of Rhodococcus rhodochrous NCIB 11,216 catalyse hydrolysis of dinitriles into cyanocarboxylic acids under mild conditions.This bioconversion was used for the highly selective synthesis of 3-cyanobenzoic acid from 1,3-dicyanobenzene.