27398-50-1

Basic information

• Product Name: 6-BROMO-2-PHENYL-1H-QUINAZOLIN-4-ONE
• Synonyms: 6-BROMO-2-PHENYL-1H-QUINAZOLIN-4-ONE;6-broMo-2-phenylquinazolin-4(3H)-one;4(1H)-Quinazolinone, 6-broMo-2-phenyl-;6-broMo-2-phenyl-3,4-dihydroquinazolin-4-one;6-Bromo-2-phenyl-3H-quinazolin-4-one
• CAS NO: 27398-50-1
• Molecular Formula: C₁₄H₉BrN₂O
• Molecular Weight: 301.14
• Mol File: 27398-50-1.mol
• Article Data: 44

Chemical Properties

• Melting Point: 303-305 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 455.5±47.0 °C(Predicted)
• Appearance: /
• Density: 1.57 g/cm³
• PKA: 6.08±0.20(Predicted)
• CAS DataBase Reference: 6-BROMO-2-PHENYL-1H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2-PHENYL-1H-QUINAZOLIN-4-ONE(27398-50-1)
• EPA Substance Registry System: 6-BROMO-2-PHENYL-1H-QUINAZOLIN-4-ONE(27398-50-1)

Safety Data

• Hazardous Substances Data: 27398-50-1(Hazardous Substances Data)

Upstream product

• 639482-27-2 2-benzamido-5-bromobenzamide 
• 189635-01-6 N-(4-bromo-2-cyanophenyl)benzamide 
• 66387-70-0 6-bromo-2-phenyl-4H-benzo[2,3-d]-1,3-oxazin-4-one 
• 21740-00-1 5-bromo-2-iodo-benzoic acid 
• 1670-14-0 benzamidine monohydrochloride 
• 98-88-4 benzoyl chloride 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 16285-28-2 6-bromo-2-phenyl-2,3-dihydro-1H-quinazolin-4-one 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 102-09-0 bis(phenyl) carbonate 
• 21719-91-5 N′-(4-bromophenyl)benzamidine 
• 3878-46-4 ethyl phenyl carbonate 

Downstream Products

• 412923-42-3 6-bromo-4-chloro-2-phenyl-quinazoline 
• 1257629-22-3 [(6-bromo-2-phenyl-4-quinazolinyl)oxy]-acetyl hydrazine 
• 1257629-15-4 C₂₀H₁₅BrN₄O₃ 
• 1257629-17-6 6-bromo-4-(1,3,4-oxadiazol-2-ylmethoxy)-2-phenylquinazoline 
• 1257629-18-7 5-{[(6-bromo-2-phenylquinazolin-4-yl)oxy]methyl}-1,3,4-oxadiazol-2(3H)-thione 
• 1257629-20-1 5-{[(6-bromo-2-phenylquinazolin-4-yl)oxy]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione 
• 1257629-21-2 C₁₈H₁₅BrN₂O₃ 
• 449196-36-5 4-[(6-bromo-2-phenylquinazoline-4-yl)amino]benzoic acid 
• 1332259-67-2 4-[(6-bromo-2-phenylquinazoline-4-yl)amino]benzohydrazide 
• 1332259-69-4 potassium 2-({4-[(6-bromo-2-phenylquinazoline-4-yl)amino]phenyl}carbonyl)hydrazine carbodithioic acid 

Relevant articles and documents

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives

A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

Microwave-mediated N-arylation of 4-chloroquinazolines in THF/H2O rapidly and efficiently afforded a library of novel 6-halo-2- phenyl-substituted 4-anilinoquinazolines. The methodology was compatible with numerous ortho-, meta-, and para-substituted N-methylanilines as well as substituted anilines and furnished the corresponding 4-anilinoquinazolines in good yields. Preliminary screening of the synthesized compounds against tumor cells (HCT-116 and T98G) showed promising antiproliferative properties.