17629-01-5

Basic information

• Product Name: 4-phenylquinazoline
• CAS NO: 17629-01-5
• Molecular Formula: C₁₄H₁₀N₂
• Molecular Weight: 206.2426
• Mol File: 17629-01-5.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 351.5°C at 760 mmHg
• Flash Point: 170.1°C
• Density: 1.176g/cm³
• Vapor Pressure: 8.32E-05mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 4-phenylquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenylquinazoline(17629-01-5)
• EPA Substance Registry System: 4-phenylquinazoline(17629-01-5)

Safety Data

• Hazardous Substances Data: 17629-01-5(Hazardous Substances Data)

Upstream product

• 1904-72-9 3,4-dihydro-4-phenylquinazoline 
• 89242-54-6 4-phenylquinazoline-2-carboxylic acid 
• 2565-30-2 formyl chloride 
• 1885-29-6 anthranilic acid nitrile 
• 29874-83-7 2-chloro-4-phenylquinazoline 
• 13209-38-6 (2-aminophenyl)(phenyl)methanol 
• 516-06-3 D,L-valine 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 529-23-7 o-aminobenzaldehyde 
• 56-40-6 glycine 
• 302-72-7 rac-Ala-OH 
• 552-89-6 2-nitro-benzaldehyde 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 79-16-3 N-methyl-acetamide 

Downstream Products

• 109271-63-8 1-(2-chloromethylbenzoyl)-1,2-dihydro-4-phenylquinazoline-2-carbonitrile 
• 109271-56-9 1-benzoyl-1,2-dihydro-4-phenylquinazoline-2-carbonitrile 
• 109271-60-5 1-(4-Methyl-benzoyl)-4-phenyl-1,2-dihydro-quinazoline-2-carbonitrile 
• 109271-58-1 1-(4-Chloro-benzoyl)-4-phenyl-1,2-dihydro-quinazoline-2-carbonitrile 
• 109271-59-2 1,2-dihydro-1-(4-methoxybenzoyl)-4-phenylquinazoline-2-carbonitrile 
• 109271-57-0 1-(4-Nitro-benzoyl)-4-phenyl-1,2-dihydro-quinazoline-2-carbonitrile 
• 109271-61-6 2-Cyano-4-phenyl-2H-quinazoline-1-carboxylic acid phenyl ester 
• 109271-62-7 1-(4-chlorobutanoyl)-1,2-dihydro-4-phenylquinazoline-2-carbonitrile 
• 1904-72-9 3,4-dihydro-4-phenylquinazoline 

Relevant articles and documents

Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines

A one-pot method for joining three separate components leading to an assortment of 4-arylquinazolines (27 examples) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed?-cascade reaction involving C(sp)-C(sp 2/s

Preparation of 4-arylquinazolines with: O-(N-alkyl, N-p-tosyl)aminobenzonitriles, aryllithiums, and NIS

The treatment of o-(N-alkyl,N-p-tosyl)aminobenzonitriles with aryllithiums, followed by the reaction with water, NIS under irradiation with a fluorescent lamp, and then tBuOK gave 2-alkyl-4-arylquinazolines or 4-arylquinazolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of iminyl radicals, the 1,6-H shift by iminyl radicals, the cyclization via 6-exo-tet mode, and finally the elimination of p-toluenesulfinate to generate 2-alkyl-4-arylquinazolines or 4-arylquinazolines.

“On-Water” Palladium-Catalyzed Tandem Cyclization Reaction for the Synthesis of Biologically Relevant 4-Arylquinazolines

The quinazoline scaffold is prevalent in pharmaceutically relevant molecules that show diverse biological activities. Herein, we report an efficient “on-water” palladium-catalyzed tandem cyclization reaction from commercially available arylboronic acids and benzonitriles that enable the rapid access to 4-arylquinazoline scaffolds in good to excellent yields (45 examples, up to 98 % yield). This protocol has shown good functional group tolerance and broad substrate scope. The reaction was also performed on a gram scale and successfully applied to the synthesis of the highly potent and selective PI3Kδ inhibitor N11, showing the practicability and synthetic utility of the protocol. In this reaction, the quinazoline scaffold is efficiently constructed with the simultaneous formation of one C?C bond and one C?N bond. Collectively, the protocol could serve as an alternative strategy to synthesize biologically important quinazoline scaffolds.