38520-78-4

Basic information

• Product Name: 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one
• Synonyms: 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one
• CAS NO: 38520-78-4
• Molecular Formula: C₉H₆FNO₂
• Molecular Weight: 179.149
• Mol File: 38520-78-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 297 °C at 760 mmHg
• Flash Point: 133.4 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 0.00139mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one(38520-78-4)
• EPA Substance Registry System: 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one(38520-78-4)

Safety Data

• Hazardous Substances Data: 38520-78-4(Hazardous Substances Data)

Usage

General Description

6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one, also known as fluotimide, is a synthetic compound with a molecular formula of C9H6FNO2. It belongs to the benzoxazine family, which are organic compounds that contain a benzene ring fused to an oxazine ring. Fluotimide exhibits a fluoro-substituted structure that imparts unique chemical properties to the compound, making it useful for various purposes. It has been studied for its potential pharmaceutical applications, particularly in the field of medicine. Additionally, it may also have implications in other industries such as agriculture, manufacturing, or material science. Further research and testing are necessary to fully understand the potential uses and implications of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one.

InChI:InChI=1/C9H6FNO2/c1-5-11-8-3-2-6(10)4-7(8)9(12)13-5/h2-4H,1H3

Upstream product

• 446-08-2 2-amino-5-fluorobenzoic acid 
• 108-24-7 acetic anhydride 
• 201230-82-2 carbon monoxide 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 1009-22-9 N-(2-bromo-4-fluorophenyl)acetamide 
• 1003-98-1 2-bromo-4-fluoroaniline 

Downstream Products

• 129687-70-3 2-Acetamino-4-fluoro-2'-methoxybenzophenone 
• 49579-08-0 6-fluoro-3-(2-fluoro-phenyl)-2-methyl-3H-quinazolin-4-one 
• 49579-12-6 3-(2-chloro-phenyl)-6-fluoro-2-methyl-3H-quinazolin-4-one 
• 49579-01-3 6-fluoro-2-methyl-3-o-tolyl-3H-quinazolin-4-one 
• 199656-43-4 3-(2-bromo-phenyl)-6-fluoro-2-methyl-3H-quinazolin-4-one 
• 212764-92-6 (S)-3-(2-chloro-phenyl)-6-fluoro-2-(2-pyridin-2-yl-vinyl)-3H-quinazolin-4-one 

Relevant articles and documents

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.

Design, Synthesis, and Structure-Activity Relationship of Quinazolinone Derivatives as Potential Fungicides

Plant diseases caused by phytopathogenic fungi reduce the yield and quality of crops. To develop novel antifungal agents, we designed and synthesized eight series of quinazolinone derivatives and evaluated their anti-phytopathogenic fungal activity. The bioassay results revealed that compounds KZL-15, KZL-22, 5b, 6b, 6c, 8e, and 8f exhibited remarkable antifungal activity in vitro. Especially, compound 6c displayed the highest bioactivity against Sclerotinia sclerotiorum, Pellicularia sasakii, Fusarium graminearum, and Fusarium oxysporum, displaying appreciable IC50 values (50% inhibitory concentration) of 2.46, 2.94, 6.03, and 11.9 μg/mL, respectively. A further mechanism interrogation revealed abnormal mycelia, damaged organelles, and changed permeability of cell membranes in S. sclerotiorum treated with compound 6c. In addition, the in vivo bioassay indicated that compound 6c possessed comparable curative and protective effects (87.3 and 90.7%, respectively) to the positive control azoxystrobin (89.5 and 91.2%, respectively) at 100 μg/mL concentration against S. sclerotiorum. This work validated the potential of compound 6c as a new and promising fungicide candidate, contributing to the exploration of potent antifungal agents.

Discovery and development of extreme selective inhibitors of the ITD and D835Y mutant FLT3 kinases

Aberrant activation of FMS-like tyrosine receptor kinase 3 (FLT3) is implicated in the pathogenesis of acute myeloid leukemia (AML) in 20–30% of patients. In this study we identified a highly selective (phenylethenyl)quinazoline compound family as novel potent inhibitors of the FLT3-ITD and FLT3-D835Y kinases. Their prominent effects were confirmed by biochemical and cellular proliferation assays followed by mice xenograft studies. Our modelling experiments and the chemical structures of the compounds predict the possibility of covalent inhibition. The most effective compounds triggered apoptosis in FLT3-ITD AML cells but had either weak or no effect in FLT3-independent leukemic and non-leukemic cell lines. Our results strongly suggest that our compounds may become therapeutics in relapsing and refractory AML disease harboring various ITD and tyrosine kinase domain mutations, by their ability to overcome drug resistance.