708-73-6

Basic information

• Product Name: 7-Chloro-2-methyl-3,1-benzoxazin-4-one
• Synonyms: 7-Chloro-2-methyl-3,1-benzoxazin-4-one
• CAS NO: 708-73-6
• Molecular Formula: C₉H₆ClNO₂
• Molecular Weight: 195.60244
• Mol File: 708-73-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 334.2°Cat760mmHg
• Flash Point: 155.9°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.00013mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 7-Chloro-2-methyl-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-2-methyl-3,1-benzoxazin-4-one(708-73-6)
• EPA Substance Registry System: 7-Chloro-2-methyl-3,1-benzoxazin-4-one(708-73-6)

Safety Data

• Hazardous Substances Data: 708-73-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H6ClNO2/c1-5-11-8-4-6(10)2-3-7(8)9(12)13-5/h2-4H,1H3

Upstream product

• 108-24-7 acetic anhydride 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 50-84-0 2,4 dichlorobenzoic acid 
• 66909-52-2 2,4-dichlorobenzoic acid potassium salt 
• 78-39-7 Triethyl orthoacetate 
• 827-66-7 N-(2-bromo-5-chlorophenyl)acetamide 
• 823-57-4 2-bromo-5-chloroaniline 

Downstream Products

• 18730-12-6 1-(4-Chlor-2-acetamido-benzamido)-guanidin 
• 34999-47-8 N-(2-benzoyl-5-chlorophenyl)acetamide 
• 74101-51-2 N-(2-Carboxy-5-chlor-phenyl)-N'-(3',5'-dimethyl-phenyl)-acetamidin 
• 7012-88-6 7-chloro-2-methylquinazolin-4(3H)-one 
• 90537-62-5 3-amino-7-chloro-2-methyl-4(3H)-quinazoline 
• 5900-56-1 2-acetylamino-4-chlorobenzoic acid 
• 340734-91-0 7-chloro-2-[2-(4-chloro-phenyl)-vinyl]-benzo[d][1,3]oxazin-4-one 
• 894-49-5 7-chloro-2-methyl-3-o-tolyl-3H-quinazolin-4-one 
• 340735-02-6 7-chloro-2-[2-(2-nitro-phenyl)-vinyl]-benzo[d][1,3]oxazin-4-one 
• 98601-72-0 (2-amino-4-chloro-phenyl)-(2-chloro-phenyl)-methanone 
• 338793-90-1 7-chloro-2-methyl-3-(1,3,4-thiadiazol-2-yl)quinazolin-4(3H)-one 
• 152911-53-0 (2-amino-4-chloro-phenyl)-(2-chloro-phenyl)-methanol 
• 152911-70-1 [4-chloro-2-(2,2-dimethyl-propylamino)-phenyl]-(2-chloro-phenyl)-methanol 
• 152911-92-7 (E)-3-[{5-Chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-(2,2-dimethyl-propyl)-carbamoyl]-acrylic acid ethyl ester 

Relevant articles and documents

Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source

A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.

4H-Benzo[d][1,3]oxazin-4-ones and Dihydro analogs from substituted anthranilic acids and orthoesters

A one-pot route to 2-alkyl and 2-aryl-4H-benzo[d][1,3]oxazin-4-ones (also known as 4H-3,1-benzoxazin-4-ones) has been developed and studied. The method involves the reaction of aryl-substitutedanthranilic acidswithorthoesters inethanol catalyzedby acetic acid. Additionally,wehave also investigated the reaction under microwave conditions. Not all of the substrates were successful in yielding the target heterocycles as some of the reactions failed to undergo the final elimination. This process led to the isolation of (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.

Distinct novel quinazolinone exhibits selective inhibition in MGC-803 cancer cells by dictating mutant p53 function

The mutant p53 proteins and their corresponding cellular response can be manipulated by novel quinazolinone derivatives 4-8 (a-i) in p53 mutant cancer cells. Of the two most potent compounds, 4a exhibited promising broad-spectrum anti-cancer effects, whereas 6c showed selective and exclusive inhibition activity in p53 mutant cancer cell lines but low toxicity to wild-type p53 cancer cell A375 and normal lung fibroblast WI-38 cells. Furthermore, 6c exhibited a more sophisticated mechanism for cell-destructive response by causing S/G2 phase arrest effect and cell size reduction. Compared with the cellular response of 6b and genetic background of cell lines studied, p53 mutation was found to be the key factor and main target for 6c evoked cell-destructive response. Molecular mechanism studies indicated that p53 phosphorylation and acetylation dual-targeting inhibitor 6c exerted anti-cancer activities with a special mechanism in evoking cell apoptosis by arresting mutant p53 function to trigger the deregulation of Cdk2 caused Bim-mediated apoptosis. To the best of our knowledge, 6c is the first quinazolinone derivative to dictate mutant p53 function for apoptotic cell death.