398-63-0

Basic information

• Product Name: 6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE
• Synonyms: 6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE;6-FLUORO-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE;BUTTPARK 120\07-74;6-fluoro-4H-1,4-benzoxazin-3-one;6-Fluoro-2,4-dihydro-1,4-benzoxazin-3-one
• CAS NO: 398-63-0
• Molecular Formula: C₈H₆FNO₂
• Molecular Weight: 167.14
• Product Categories: API intermediates;Benzoxazines;Building Blocks;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Others
• Mol File: 398-63-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 207-211 °C(lit.)
• Boiling Point: 322.9 °C at 760 mmHg
• Flash Point: 149.1 °C
• Appearance: /
• Density: 1.347 g/cm³
• Vapor Pressure: 0.00027mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE(398-63-0)
• EPA Substance Registry System: 6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE(398-63-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 398-63-0(Hazardous Substances Data)

Usage

Description

6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE is a chemical compound characterized by the presence of a halogen (fluorine) at the C-6 position. This feature endows the molecule with significant phytotoxic activity, making it a compound of interest in various applications.

Uses

Used in Agricultural Industry:
6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE is used as a phytotoxic agent for controlling the growth of unwanted plants and weeds. Its ability to inhibit plant growth makes it a potential candidate for use in herbicides, helping to protect crops and improve agricultural yields.
Used in Pharmaceutical Industry:
6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties can be exploited to develop new drugs with potential applications in treating different diseases and medical conditions.
Used in Chemical Research:
6-FLUORO-2H-1,4-BENZOXAZIN-3(4H)-ONE serves as a valuable compound for research purposes in the field of organic chemistry. Its study can lead to a better understanding of the properties and reactivity of halogenated benzoxazinones, which may contribute to the development of new chemical processes and applications.

InChI:InChI=1/C8H6FNO2/c9-5-1-2-7-6(3-5)10-8(11)4-12-7/h1-3H,4H2,(H,10,11)

Upstream product

• 396-15-6 (4-fluoro-2-nitro-phenoxy)-acetic acid 
• 405-79-8 2-(4-fluorophenoxy)ethanoic acid 
• 100638-16-2 ethyl 4-fluoro-2-nitrophenoxyacetate 
• 1249633-21-3 2-(4-fluoro-2-nitrophenoxy)acetonitrile 
• 394-33-2 2-nitro-4-fluorophenol 
• 399-97-3 2-amino-4-fluorophenol 
• 598-21-0 2-Bromoacetyl bromide 
• 1247501-95-6 (4-fluoro-6-nitrophenoxy)acetic acid methyl ester 
• 371-41-5 4-Fluorophenol 
• 55444-93-4 (4-fluorophenoxy)acetic acid methyl ester 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 131637-37-1 4-{3-[4-(2-Chloro-phenyl)-9-methyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-2-yl]-prop-2-ynyl}-6-fluoro-4H-benzo[1,4]oxazin-3-one 
• 105655-00-3 6-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine 
• 1245276-87-2 (Z)-2,6-dibromo-4-{(6-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ylidene)methyl}phenyl acetate 
• 1350659-88-9 6-fluoro-4-[5-(3-morpholinophenoxy)pyrimidin-2-yl]-3,4-dihydro-2H-benzo[1,4]oxazine 

Relevant articles and documents

Synthesis, docking, 3-D-qsar, and biological assays of novel indole derivatives targeting serotonin transporter, dopamine D2 receptor, and mao-a enzyme: In the pursuit for potential multitarget directed ligands

A series of 27 compounds of general structure 2,3-dihydro-benzo[1,4]oxazin-4-yl)-2-{4-[3-(1H-3indolyl)-propyl]-1-piperazinyl}-ethanamides, Series I: 7(a-o) and (2-{4-[3-(1H-3-indolyl) -propyl]-1-piperazinyl}-acetylamine)-N-(2-morfolin-4-yl-ethyl)-fluorinated benzamides Series II: 13(a-l) were synthesized and evaluated as novel multitarget ligands towards dopamine D2 receptor, serotonin transporter (SERT), and monoamine oxidase-A (MAO-A) directed to the management of major depressive disorder (MDD). All the assayed compounds showed affinity for SERT in the nanomolar range, with five of them displaying Ki values from 5 to 10 nM. Compounds 7k, Ki = 5.63 ± 0.82 nM, and 13c, Ki = 6.85 ± 0.19 nM, showed the highest potencies. The affinities for D2 ranged from micro to nanomolar, while MAO-A inhibition was more discrete. Nevertheless, compounds 7m and 7n showed affinities for the D2 receptor in the nanomolar range (7n: Ki = 307 ± 6 nM and 7m: Ki = 593 ± 62 nM). Compound 7n was the only derivative displaying comparable affinities for SERT and D2 receptor (D2/SERT ratio = 3.6) and could be considered as a multitarget lead for further optimization. In addition, docking studies aimed to rationalize the molecular interactions and binding modes of the designed compounds in the most relevant protein targets were carried out. Furthermore, in order to obtain information on the structure-activity relationship of the synthesized series, a 3-D-QSAR CoMFA and CoMSIA study was conducted and validated internally and externally (q2 = 0.625, 0.523 for CoMFA and CoMSIA and r2ncv = 0.967, 0.959 for CoMFA and CoMSIA, respectively).

Using gene expression database to uncover biology functions of 1,4-disubstituted 1,2,3-triazole analogues synthesized via a copper (I)-catalyzed reaction

We have synthesized bioactive 1,4-disubstituted 1,2,3-triazole analogues containing 2H-1,4-benzoxazin-3-(4H)-one derivatives via 1,3-dipolar cycloaddition in the presence of CuI. All the reactions proceeded smoothly and afforded its desired products in excellent yields. Among these analogues, 3y exhibited a better cytotoxic effect on human hepatocellular carcinoma (HCC) Hep 3B cells and displayed less cytotoxicity on normal human umbilical vein endothelial cells, compared with Sorafenib, a targeted therapy for advanced HCC. 3y also induced stronger apoptosis and autophagy. Addition of curcumin enhanced 3y-induced cytotoxicity by further induction of autophagy. Using gene expression signatures of 3y to query Connectivity Map, a glycogen synthase kinase-3 inhibitor (AR-A014418) was predicted to display similar molecular action of 3y. Experiments further demonstrate that AR-A014418 acted like 3y, and vice versa. Overall, our data suggest the chemotherapeutic potential of 3y on HCC.

TRICYCLIC SULFONAMIDE DERIVATIVES

The invention relates to derivatives of formula (I), wherein the substituents are as defined in the specification; to processes for the preparation of such derivatives; pharmaceutical compositions comprising such derivatives; such derivatives as a medicament; such derivatives for the treatment of pain.