36082-71-0

Basic information

• Product Name: QUINAZOLINE-4-CARBONITRILE
• Synonyms: QUINAZOLINE-4-CARBONITRILE;4-Cyanoquinazoline
• CAS NO: 36082-71-0
• Molecular Formula: C₉H₅N₃
• Molecular Weight: 155.16
• Mol File: 36082-71-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 334.1°C at 760 mmHg
• Flash Point: 118.1°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.000131mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: QUINAZOLINE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: QUINAZOLINE-4-CARBONITRILE(36082-71-0)
• EPA Substance Registry System: QUINAZOLINE-4-CARBONITRILE(36082-71-0)

Safety Data

• Hazardous Substances Data: 36082-71-0(Hazardous Substances Data)

Usage

General Description

QUINAZOLINE-4-CARBONITRILE is a chemical compound with the molecular formula C9H6N4. It is a heterocyclic organic compound containing a quinazoline ring system with a carbonitrile functional group. QUINAZOLINE-4-CARBONITRILE is utilized in the pharmaceutical industry as a building block for the synthesis of a variety of biologically active compounds, including potential therapeutic agents. QUINAZOLINE-4-CARBONITRILE has shown potential as an intermediate in the synthesis of various pharmaceuticals, and its unique structure makes it a valuable component in drug discovery and development. Additionally, it has also been studied for its potential use in organic synthesis and chemical research.

InChI:InChI=1/C9H5N3/c10-5-9-7-3-1-2-4-8(7)11-6-12-9/h1-4,6H

Upstream product

• 151-50-8 potassium cyanide 
• 187336-04-5 4-(α-benzyl-α-hydroxybenzyl)quinazoline 
• 187336-15-8 (4-Methoxy-phenyl)-phenyl-quinazolin-4-yl-methanol 
• 187336-13-6 1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol 
• 187336-14-7 1-(4-methoxyphenyl)-2-phenyl-1-(quinazoline-4-yl)ethanol 
• 99933-52-5 Benzoic acid cyano-(3-nitro-phenyl)-quinazolin-4-yl-methyl ester 
• 99933-51-4 Benzoic acid cyano-(4-nitro-phenyl)-quinazolin-4-yl-methyl ester 
• 99933-48-9 Benzoic acid cyano-phenyl-quinazolin-4-yl-methyl ester 
• 76051-72-4 2,4-dicyano-1,3-dibenzoyl-1,2,3,4-tetrahydroquinazoline 
• 100-52-7 benzaldehyde 
• 92736-32-8 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile 
• 99933-56-9 (4-Nitro-phenyl)-quinazolin-4-yl-methanone 
• 99933-49-0 Benzoic acid (4-chloro-phenyl)-cyano-quinazolin-4-yl-methyl ester 

Relevant articles and documents

Carbon-carbon bond cleavage of α-hydroxybenzylheteroarenes catalyzed by cyanide ion: Retro-benzoin condensation affords ketones and heteroarenes and benzyl migration affords benzylheteroarenes and arenecarbaldehydes

4-(α-Benzylα-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford kelones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybelzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4- aroylquinazolines (34), using the aroyl group as a protecting and electron- withdrawing group.

Reissert Compound Studies. LXI. Preparation and Reactions of Quinazoline Di-Reissert Compounds

Various di-Reissert compounds and analogs were prepared from quinazoline by use of trimethylsilyl cyanide together with a catalytic amount of anhydrous aluminum chloride.Reactions of these quinazoline di-Reissert compounds are reported.

Reaction of 4-Aroylquinazolines with Sodium Hydroxide: Aryl Migration to Give 4-Aryl-3,4-dihydro-4-quinazolinecarboxylic Acids and Formation of Quinazoline and Aroic Acids

4-Aroylquinazolines (3) were prepared in good yields by alkaline hydrolysis of α-aryl-4-quinazolinylmethyl benzoates (15), followed by oxidation.The reaction of 3 with sodium hydroxide in dimethyl sulfoxide(DMSO) was found to proceed in two ways.One path is the aryl migration to lead to 4-aryl-3,4-dihydro-4-quinazolinecarboxylic acids (4), and the other is the fission of the C4-CO bond to yield quinazoline (5) and aroic acids (6). Potassium ferricyanide oxidized the carboxylic acids 4 to the corresponding 4-arylquinazolines (14) with elimination of carbon dioxide. Reaction of 4-benzoylquinazoline (3a) with methylmagnesium iodide did not result in the migration, but instead yielded of α-methyl-α-phenyl-4-quinazolinemethanol (18) and 3,4-dihydro-α,4-dimethyl-α-phenyl-4-quinazolinemethanol (19).