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

Description

QUINAZOLINE-4-CARBONITRILE, with the molecular formula C9H6N4, is a heterocyclic organic compound that features a quinazoline ring system fused with a carbonitrile functional group. QUINAZOLINE-4-CARBONITRILE is recognized for its role as a key building block in the pharmaceutical industry, where it contributes to the synthesis of a diverse array of biologically active molecules, including potential therapeutic agents. Its distinctive structure positions it as a significant player in drug discovery and development, as well as in the realm of organic synthesis and chemical research.

Uses

Used in Pharmaceutical Industry:
QUINAZOLINE-4-CARBONITRILE is used as a building block for the synthesis of biologically active compounds due to its unique quinazoline ring system and carbonitrile functional group. It plays a crucial role in the development of potential therapeutic agents, contributing to the creation of new medicines with diverse pharmacological properties.
Used in Drug Discovery and Development:
As an intermediate in the synthesis of various pharmaceuticals, QUINAZOLINE-4-CARBONITRILE is utilized for its potential to enhance the properties of drug candidates, making it a valuable component in the advancement of novel treatments and therapies.
Used in Organic Synthesis and Chemical Research:
Beyond its pharmaceutical applications, QUINAZOLINE-4-CARBONITRILE is also employed in organic synthesis and chemical research, where its distinctive structure allows for the exploration of new chemical reactions and the development of innovative synthetic pathways.

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

Upstream product

• 187336-13-6 1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol 
• 187336-15-8 (4-Methoxy-phenyl)-phenyl-quinazolin-4-yl-methanol 
• 151-50-8 potassium cyanide 
• 187336-04-5 4-(α-benzyl-α-hydroxybenzyl)quinazoline 
• 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 
• 99933-49-0 Benzoic acid (4-chloro-phenyl)-cyano-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 

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.

Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles

Reactions of the quinazoline Reissert compound (2) with various electrophiles in the presence of sodium hydride in N,N-dimethylformamide were investigated.The reactions with aldehydes (3) and ketones (12) gave α-aryl (or alkyl)-(7) and α-alkyl-α-aryl (or alkyl)-4-quinazolinylmethyl benzoates (16), respectively.The reaction with ?-deficient heteroaromatics (10a-c) gave 4-heteroarylquinazolines (20a-c).Alkylation (or arylation) with alkyl (or aryl) halides (23a-c) afforded 4-substituted 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitriles (24a-c).The reaction with dimethyl acetylenedicarboxylate proceeded in two ways, giving dimethyl 3-phenylpyrroloquinazoline-1,2-dicarboxylate (27) and dimethyl 3-benzoyl-4-cyano-1,2,3,4-tetrahydro-2,4-ethenoquinazoline-9,10-dicarboxylate (28).The reaction with 2-alkenonitriles (29a,b) resulted in the formation of 2-benzoyl-3-(4-quinanolinyl)alkanonitriles (32a,b).Keywords - rearrangement; substitution; 1,3-dipolar addition; quinazoline Reissert compound anion; α-substituted 4-quinazolinylmethyl benzoate; 4-heteroarylquinazoline; 4-substituted 3,4-dihydro-4-quinazoline carbonitrile; pyrroloquinazoline; 2,4-ethenoquinazoline; 2-benzoyl-3-(4-quinazolinyl)alkanonitrile