945-26-6

Usage

Chemical compound

2-Propenenitrile, 2-methyl-3-(2-nitrophenyl)-

Use

Building block in synthesis of pharmaceuticals and agrochemicals

Physical properties

Pale yellow to yellow crystalline solid, melting point of 80-82°C

Solubility

Insoluble in water, soluble in organic solvents

Potential use

Versatile intermediate in organic synthesis

Biological activity

Valuable compound in medicinal chemistry

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 29668-61-9 diethyl (1-cyanoethyl)phosphonate 

Downstream Products

• 74844-99-8 2-amino-3-methylquinoline 

Relevant academic research and scientific papers

One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile

α-Diaminoboryl carbanions, readily prepared from acetonitrile, stereoselectively convert 2-nitrobenzaldehydes into nitrophenyl (Z)-acrylonitriles. Subsequent reductive cyclization leads to a series of 2-aminoquinoline derivatives. The entire procedure is practically operated in a single flask.

A short and versatile synthesis of 3-substituted 2-aminoquinolines

A short and versatile synthesis of a series of 3-substituted 2-aminoquinolines was accomplished in good yields starting from 2-nitrobenzaldehyde. Organic phosphonates were used as key synthetic intermediates and in some cases amino acids as readily available starting materials. The final two key steps of the sequence involving a reduction and ring closure that led to the 2-aminoquinoline skeleton were carried out in a 'one pot' procedure using SnCL22H2O.