71526-47-1

Basic information

• Product Name: 2H-3,1-Benzoxazin-2-one, 1,4-dihydro-4,4-diphenyl-
• Synonyms: 4,4-Diphenyl-1,4-dihydro-benz[d][1,3]oxazin-2-on;4,4-Diphenyl-3,1-benzoxazin-2-on;4,4-diphenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-one;4,4-diphenyl-1,4-dihydro-2H-3,1-benzoxazin-2-one;4,4-diphenyl-1,4-dihydro-benz[d][1,3]oxazin-2-one;4,4-diphenyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one;2H-3,1-Benzoxazin-2-one,1,4-dihydro-4,4-diphenyl
• CAS NO: 71526-47-1
• Molecular Formula: C20H15NO2
• Molecular Weight: 301.345
• Mol File: 71526-47-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2H-3,1-Benzoxazin-2-one, 1,4-dihydro-4,4-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-3,1-Benzoxazin-2-one, 1,4-dihydro-4,4-diphenyl-(71526-47-1)
• EPA Substance Registry System: 2H-3,1-Benzoxazin-2-one, 1,4-dihydro-4,4-diphenyl-(71526-47-1)

Safety Data

• Hazardous Substances Data: 71526-47-1(Hazardous Substances Data)

Upstream product

• 1922-79-8 3,3-diphenyl-1,3-dihydro-indol-2-one 
• 5100-23-2 2-isocyanatobenzoyl chloride 
• 71-43-2 benzene 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 62-53-3 aniline 
• 134-20-3 2-carbomethoxyaniline 
• 67-56-1 methanol 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 87-25-2 2-ethoxycarbonylaniline 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 36192-63-9 2-amino-4'-methylbenzophenone 
• 7732-18-5 water 
• 64-19-7 acetic acid 

Downstream Products

• 602-56-2 9-phenylacridine 
• 52744-72-6 (2-aminophenyl)diphenylmethanol 
• 57259-32-2 (2-aminophenyl)diphenylmethane 

Relevant articles and documents

Friedel-Crafts Acylation with 2-Isocyanatobenzoyl Chlorides: The Structure of the Intermediate Complex

The intermediate complex obtained in the Friedel-Crafts acylation of benzene with 2-isocyanatobenzoyl chloride (1a) reacts with methanol or ethanol in the presence of ether affording 4-alkoxy-4-phenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-ones, whereas with anilines, the corresponding anils of 2-aminobenzophenone are obtained.In the presence of triethylamine, the complex reacts with aniline and 2-aminobenzophenone affording 4-hydroxy-4-phenyl-3-substituted 3,4-dihydroquinazolin-2(1H)-ones whereas, with alkyl anthranilates, the new 11b-phenyl-7,11b-dihydroquinazolinobenzoxazine-6,13-diones are obtained.Similar products are also obtained from 5-chloro-2-isocyanatobenzoyl chloride.The intermediate complex has been shown to exist exclusively in the cyclic form in both acidic and basic media.

Friedel-Crafts Acylation of Some Aromatic Compounds with 2-Isocyanatobenzoyl Chloride

Friedel-Crafts acylation of benzene, toluene, anisole and chlorobenzene with 2-isocyanatobenzoyl chloride (1) afford either 2-aminobenzophenones (2) or 4,4-diaryl-1,2-dihydro-3,1-benzoxazin-2(4H)-ones (3) as major products depending on reaction temperature and/or substrate reactivity.Other minor products isolated are 3-aryl-1,2,3,4-tetrahydroquinazoline-2,4-diones (4), 6,12-diaryldibenzodiazocines (6) and 2-aminophenyl-α,α-diarylmethanols (7).The formation of 2 and 3 has been shown to take place via a common intermediate complex to which the cyclic 4-aryl-3,1-benzoxazinonium ion structure (12) has been assigned on the basis of its rection with methanol and 2-aminobenzophenone.While the formation of 6 occurs through the intermediate complex (12), 4-aryliminoquinazolin-2-ones (5) are formed most probably from the 1-AlCl3 complex.