7033-50-3

Basic information

• Product Name: 6-chloro-2-methyl-4H-3,1-benzoxazin-4-one
• Synonyms: 6-Chloro-2-methyl-4H-3,1-benzoxazin-4-one
• CAS NO: 7033-50-3
• Molecular Formula: C₉H₆ClNO₂
• Molecular Weight: 195.6024
• Mol File: 7033-50-3.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 334.2°C at 760 mmHg
• Flash Point: 155.9°C
• Density: 1.42g/cm³
• Vapor Pressure: 0.00013mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 6-chloro-2-methyl-4H-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-2-methyl-4H-3,1-benzoxazin-4-one(7033-50-3)
• EPA Substance Registry System: 6-chloro-2-methyl-4H-3,1-benzoxazin-4-one(7033-50-3)

Safety Data

• Hazardous Substances Data: 7033-50-3(Hazardous Substances Data)

Usage

Biological activities

anti-inflammatory, anti-cancer, insecticidal, anti-fungal
Potential agricultural applications
Potential in the development of new drugs for various diseases

Upstream product

• 108-24-7 acetic anhydride 
• 635-21-2 5-chloroanthranilic acid 
• 5202-87-9 2-acetamido-5-chlorobenzoic acid 
• 201230-82-2 carbon monoxide 
• 63069-48-7 p-chloro-o-iodoaniline 

Downstream Products

• 102023-71-2 4-(6-chloro-2-methyl-4-oxo-4H-quinazolin-3-yl)-benzenesulfonic acid-[2]pyridylamide 
• 107919-09-5 4-(6-chloro-2-methyl-4-oxo-4H-quinazolin-3-yl)-benzenesulfonic acid thiazol-2-ylamide 
• 62175-53-5 5-(2-acetylamino-5-chloro-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 34999-45-6 N-(4-chloro-2-(4-chlorobenzoyl)phenyl)acetamide 
• 34999-44-5 5-Chlor-2--4'-methoxy-benzophenon 
• 34999-43-4 N-(4-chloro-2-(4-methylbenzoyl)phenyl)acetamide 
• 34999-46-7 N-(2-(4-fluorobenzoyl)-4-chlorophenyl)acetamide 
• 2894-64-6 2-Acetamino-4-chloro-2'-methoxybenzophenone 
• 73268-16-3 5-chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzoic acid 
• 62492-51-7 2-Acetylamino-5-chlor-3'-methoxy-benzophenon 
• 963-33-7 6-chloro-2-methyl-3-o-tolyl-3H-quinazolin-4-one 
• 152909-08-5 2-amino-5-chloro-2',4',-6'-trimethoxybenzophenone 
• 152911-43-8 (2-amino-5-chlorophenyl)(2,3-dimethoxyphenyl)methanone 
• 406684-57-9 (2-amino-5-chloro-phenyl)-(2-methoxy-3-methyl-phenyl)-methanone 

Relevant articles and documents

Synthesis of 5-chloro-2-methyl-3-(5-methylthiazol-2-yl)-4(3H)-quinazolinone and related compounds with potential biological activity

Eight new 2-methyl-4(3H)-quinazolinones (8a-8d, 9c, 9d, 10c, 10d) with one or two chlorine atoms in the benzene ring and a 5-methyl-1,3-thiazol-2-yl, 4-methyl-1,3-thiazol-2-yl, and 5-ethyl-1,3,4-thiadiazol-2-yl substituent in position 3 of the heterocyclic ring were synthesized and characterized. The two step procedure (Scheme 1) utilizes chlorosubstituted anthranilic acids (3a-3d) and acetic anhydride as the starting materials, with the respective chlorosubstituted 2-methyl-4H-3,1-benzoxazin-4-ones (4a-4d) as the intermediates. The quinazoline derivatives were characterized by their melting points, elemental analyses and the mass, ultraviolet, infrared, and 1H and 13C nmr spectra. The new compounds are expected to be biologically active.

Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones

A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance and good to excellent yields. This supported palladium complex can be readily separated from the product and recovered by a simple filtration of the reaction solution and reused up to seven times with almost consistent catalytic efficiency.

Novel Hydroxamic Acid Incorporating Quinazolin-4(3H)-ones as Histone Deacetylase Inhibitors and Anticancer Composition Comprising the Same

The compound according HDAC(histone deacetylase) to the present -4(3H)- won invention can, be used as an active. ingredient of, a potent anticancer agent, HDAC since the compound according, to the present invention can be used. as, an active ingredient of a potent anticancer agent, since the compound. according to the present invention can be used as an active ingredient of a potent anticancer agent. (by machine translation)

Quinazolin-4(3H)-one-Based Hydroxamic Acids: Design, Synthesis and Evaluation of Histone Deacetylase Inhibitory Effects and Cytotoxicity

The present article describes the synthesis and biological activity of various series of novel hydroxamic acids incorporating quinazolin-4(3H)-ones as novel small molecules targeting histone deacetylases. Biological evaluation showed that these hydroxamic acids were potently cytotoxic against three human cancer cell lines (SW620, colon; PC-3, prostate; NCI?H23, lung). Most compounds displayed superior cytotoxicity than SAHA (suberoylanilide hydroxamic acid, Vorinostat) in term of cytotoxicity. Especially, N-hydroxy-7-(7-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5b) and N-hydroxy-7-(6-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5c) (IC50 values, 0.10–0.16 μm) were found to be approximately 30-fold more cytotoxic than SAHA (IC50 values of 3.29–3.67 μm). N-Hydroxy-7-(4-oxoquinazolin-3(4H)-yl)heptanamide (5a; IC50 values of 0.21–0.38 μm) was approximately 10- to 15-fold more potent than SAHA in cytotoxicity assay. These compounds also showed comparable HDAC inhibition potency with IC50 values in sub-micromolar ranges. Molecular docking experiments indicated that most compounds, as represented by 5b and 5c, strictly bound to HDAC2 at the active binding site with binding affinities much higher than that of SAHA.