321-50-6

Basic information

• Product Name: 7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE
• Synonyms: 7-FLUORO-2H-3,1-BENZOXAZINE-2,4(1H)-DIONE;7-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione;2H-3,1-Benzoxazine-2,4(1H)-dione, 7-fluoro-;7-Fluoroisatoic anhydride;7-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione, 7-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione;7-fluoro-1H-3,1-benzoxazine-2,4-dione
• CAS NO: 321-50-6
• Molecular Formula: C₈H₄FNO₃
• Molecular Weight: 181.12
• Mol File: 321-50-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 229-231 °C (decomp)
• Appearance: /
• Density: 1.503 g/cm³
• Refractive Index: 1.561
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.91±0.20(Predicted)
• CAS DataBase Reference: 7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE(321-50-6)
• EPA Substance Registry System: 7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE(321-50-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 321-50-6(Hazardous Substances Data)

Usage

Description

7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE, also known as 7-Fluoro-1H-benzodioxazin-2,4-dione, is a heterocyclic chemical compound with the molecular formula C8H4FNO3. It features a benzoxazine ring fused with a dione functional group, which endows it with unique chemical properties and reactivity. 7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE serves as a versatile building block in organic synthesis and pharmaceutical research, making it a significant intermediate in the production of fine chemicals and pharmaceuticals.

Uses

Used in Pharmaceutical Research and Development:
7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE is used as a key intermediate in the synthesis of various drugs and biologically active compounds. Its unique structure and reactivity contribute to the development of novel therapeutic agents with potential applications in treating a wide range of diseases and medical conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE is employed as a valuable building block for the creation of complex organic molecules. Its benzoxazine ring and dione functional group provide opportunities for further chemical modifications and reactions, enabling the synthesis of a diverse array of organic compounds with various applications.
Used in Fine Chemical Production:
7-FLUORO-1-H-BENZO[D][1,3]OXAZINE-2,4-DIONE plays a crucial role in the production of fine chemicals, which are high-purity chemicals used in various industries, including pharmaceuticals, agriculture, and materials science. Its properties and reactivity make it an essential component in the synthesis of specialty chemicals with specific functions and applications.

InChI:InChI=1/C8H4FNO3/c9-4-1-2-5-6(3-4)10-8(12)13-7(5)11/h1-3H,(H,10,12)

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 119023-25-5 4-fluoroanthranilamide 
• 399-51-9 6-fluoro-1H-indole 
• 75-44-5 phosgene 
• 446-32-2 4-fluoroanthranilic acid 
• 503-38-8 trichloromethyl chloroformate 
• 324-03-8 6-fluoroisatin 

Downstream Products

• 1464831-57-9 10-fluoro-5-phenylindazolo[3,2-b]quinazolin-7-one 
• 194473-03-5 7-fluoro-2-methylquinazolin-4(3H)-one 
• 119023-25-5 4-fluoroanthranilamide 

Relevant articles and documents

Synthesis of Ring-Fused, N-Substituted 4-Quinolinones Using p Ka-Guided, Base-Promoted Annulations with Isatoic Anhydrides: Total Synthesis of Penicinotam

An anionic annulation strategy employing isatoic anhydrides and a wide assortment of enolizable partners was developed to afford over 80 novel ring-fused, N-substituted 4-quinolinones, an underrepresented privileged template. Multiple factors governing the efficiency of the transformation were determined, resulting in a reliable and tunable synthetic platform applicable for a broad range of substrates with variable deprotonation susceptibility, such as tetramic and tetronic acids, cyclic 1,3-diketones, and cycloalkanones. Application to the synthesis of bioactive, pyrrolizine-fused 4-quinolinone, penicinotam 3, resulted in the most brief and highest yielding total synthesis of the alkaloid in three steps and a 36% overall yield.

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.

Target Elucidation by Cocrystal Structures of NADH-Ubiquinone Oxidoreductase of Plasmodium falciparum (PfNDH2) with Small Molecule To Eliminate Drug-Resistant Malaria

Drug-resistant malarial strains have been continuously emerging recently, which posts a great challenge for the global health. Therefore, new antimalarial drugs with novel targeting mechanisms are urgently needed for fighting drug-resistant malaria. NADH-ubiquinone oxidoreductase of Plasmodium falciparum (PfNDH2) represents a viable target for antimalarial drug development. However, the absence of structural information on PfNDH2 limited rational drug design and further development. Herein, we report high resolution crystal structures of the PfNDH2 protein for the first time in Apo-, NADH-, and RYL-552 (a new inhibitor)-bound states. The PfNDH2 inhibitor exhibits excellent potency against both drug-resistant strains in vitro and parasite-infected mice in vivo via a potential allosteric mechanism. Furthermore, it was found that the inhibitor can be used in combination with dihydroartemisinin (DHA) synergistically. These findings not only are important for malarial PfNDH2 protein-based drug development but could also have broad implications for other NDH2-containing pathogenic microorganisms such as Mycobacterium tuberculosis.