56341-31-2

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-9H-XANTHEN-9-ONE is used as a pharmaceutical compound for its potential antitumor, antidiabetic, and antihypertensive activity. Its chemical structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs to treat cancer, diabetes, and hypertension.
Used in Anticancer Applications:
In the field of oncology, 2-BROMO-9H-XANTHEN-9-ONE is used as an anticancer agent due to its potential to target and inhibit tumor growth. Its oxygenated heterocycle structure enables it to modulate various oncological signaling pathways, which can lead to the inhibition of tumor progression and the enhancement of the effectiveness of conventional chemotherapeutic drugs.
Used in Antidiabetic Applications:
2-BROMO-9H-XANTHEN-9-ONE is used as an antidiabetic agent, where it may help in the regulation of blood sugar levels and improve insulin sensitivity. Its potential to target specific metabolic pathways involved in diabetes makes it a valuable compound for the development of new treatments for diabetes.
Used in Antihypertensive Applications:
In the context of cardiovascular health, 2-BROMO-9H-XANTHEN-9-ONE is used as an antihypertensive agent. Its ability to modulate blood pressure regulation mechanisms can contribute to the development of new therapies for the treatment of hypertension and related cardiovascular diseases.
Overall, 2-BROMO-9H-XANTHEN-9-ONE is a versatile compound with potential applications in various industries, particularly in the pharmaceutical sector, where its unique properties make it a promising candidate for the development of new drugs to address a range of health conditions.

InChI:InChI=1/C13H7BrO2/c14-8-5-6-12-10(7-8)13(15)9-3-1-2-4-11(9)16-12/h1-7H

Upstream product

• 90-47-1 xanth-9-one 
• 106-41-2 4-bromo-phenol 
• 118-91-2 ortho-chlorobenzoic acid 
• 4068-76-2 5-bromo-2-hydroxy-benzoic acid methyl ester 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 50-78-2 aspirin 
• 364323-77-3 2-(4-bromophenoxy)benzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 446-52-6 2-Fluorobenzaldehyde 
• 139139-81-4 bis(4-bromophenyl)iodonium triflate 
• 119-36-8 methyl salicylate 
• 54313-98-3 2-bromo-9H-xanthene 
• 182056-39-9 2-bromo-4-iodo-1-methoxybenzene 
• 393-52-2 2-Fluorobenzoyl chloride 

Downstream Products

• 40102-85-0 2,7-dibromo-9H-xanthen-9-one 
• 1166397-96-1 2-(2,6-dimethylphenyl)-9H-xanthen-9-one 
• 1316277-17-4 C₁₃H₈BrNO₂ 
• 1316277-23-2 C₁₃H₈BrNO₂ 
• 1316277-24-3 C₁₉H₁₃NO₂ 
• 1316277-18-5 C₁₉H₁₃NO₂ 
• 1316277-21-0 3-[2'-hydroxy-4'-bromophenyl]-5-bromo-1,2-benzisoxazole 
• 1316277-22-1 3-[2'-hydroxy-4'-phenylphenyl]-5-phenyl-1,2-benzisoxazole 
• 1316277-30-1 C₁₃H₈BrNO₃ 
• 1316277-35-6 C₁₃H₈BrNO₃ 
• 1316277-36-7 C₁₉H₁₃NO₃ 
• 1316277-31-2 C₁₉H₁₃NO₃ 
• 1316277-33-4 3-[2'-hydroxy-4'-bromophenyl]-5-bromo-1,2-benzisoxazole 2-oxide 
• 1316277-34-5 3-[2'-hydroxy-4'-phenylphenyl]-5-phenyl-1,2-benzisoxazole 2-oxide 

Relevant academic research and scientific papers

Synthesis of xanthones from 4-(2-phenoxyphenyl)-1-tosyl-1H-1,2,3-triazole via rhodium-catalyzed annulation/oxidation

A series of xanthone derivatives were synthesized by rhodium-catalyzed cycloaddition and sequential oxidation. The derivatives synthesized for excellent yields, including electron-withdrawing and electron-donating substituents, demonstrated the wide applicability of the proposed approach. The xanthones synthesized with different substituent electron effects may go through the same intermediate via two cycloadditions. It is highlighted that the protocol was exemplified by its successful integration into a one-pot synthesis directly from 1-ethynyl-2-phenoxybenzene. We believe that the current method may be an attractive option for the synthesis of xanthone and its derivatives.

Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis

A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.

Regioselective Bromine/Magnesium Exchange for the Selective Functionalization of Polyhalogenated Arenes and Heterocycles

Using the bimetallic combination sBu2Mg?2 LiOR (R=2-ethylhexyl) in toluene enables efficient and regioselective Br/Mg exchanges with various dibromo-arenes and -heteroarenes under mild reaction conditions and provides bromo-substituted magnesiu

Ultraviolet-light-induced aerobic oxidation of benzylic C(sp3)-H of alkylarenes under catalyst- and additive-free conditions

A mild and efficient system has been discovered for the synthesis of α-aryl carbonyl compounds via oxidation of benzylic C–H to C[dbnd]O bonds. This ultraviolet-light-mediated oxygenation reaction exhibited excellent substrate scope including various xanthenes, thioxanthenes and 9, 10-dihydroacridines and afforded the corresponding ketones with good to excellent yields under catalyst- and additive-free conditions at room temperature.

Synthesis of xanthones, thioxanthones and Acridones by a metal-free photocatalytic oxidation using visible light and molecular oxygen

9H-Xanthenes, 9H-thioxanthenes and 9,10-dihydroacridines can be easily oxidized to the corresponding xanthones, thioxanthones and acridones, respectively, by a simple photo-oxidation procedure carried out using molecular oxygen as oxidant under the irradiation of visible blue light and in the presence of riboflavin tetraacetate as a metal-free photocatalyst. The obtained yields are high or quantitative.

A Green Nanopalladium-Supported Catalyst for the Microwave-Assisted Direct Synthesis of Xanthones

We report an efficient, selective, rapid and eco-friendly protocol for the one-step synthesis of a small xanthone library via an intermolecular catalytic coupling from readily available salicylaldehydes and 1,2-dihaloarenes under ligand-free conditions. To achieve this advantageous direct annulation, we used a novel recoverable palladium nanocatalyst supported on a green biochar under microwave irradiation. Unlike other existing palladium-based approaches, our synthetic strategy showed a greater operational simplicity, drastic reduction in reaction times, and an excellent tolerance to diverse functional groups. The reaction proceeds in very good yields and with high regioselectivity. The novel heterogeneous catalyst can be recycled and reused up to four times without significant loss of activity.

Ultraviolet light promoted synthesis method of xanthone compounds

The invention discloses an ultraviolet light promoted synthesis method of a xanthone compound. The method comprises the steps: by taking a xanthene compound as a reaction substrate and oxygen in air as an oxidant, carrying out a reaction on the reaction substrate in an organic solvent at normal temperature under the condition of 380-385 nm ultraviolet irradiation, and after the reaction is finished, carrying out separation treatment to obtain the xanthone compound. According to the synthesis method disclosed by the invention, a traditional heating reaction is replaced by an illumination reaction, so that energy sources can be saved; no catalyst is used.

Benzylic oxidation and functionalizations of xanthenes by ligand trasfer reactions of hypervalent iodine reagents

The benzylic oxidation, amidation, and unprecedented heteroarylation proceed at room temperature using iodosobenzene, (sulfonylimido)iodobenzenes, and diaryliodonium(III) salts are described for the direct Csp3-H functionalizations of xanthene molecules. This study has demonstrated that hypervalent iodine reagents serve as unified synthetic tools for versatile xanthene Csp3-H transformations based on the radical and SET oxidation processes.

Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H cross-dehydrogenative coupling (CDC)

A Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H bond cross-dehydrogenative coupling of 2-aryloxybenzaldehydes is described. A variety of substituted xanthone derivatives are synthesized in moderate to excellent yields. Reaction can also be extended to the synthesis of 9H-thioxanthen-9-one 10,10-dioxide and phenanthridin-6(5H)-ones, respectively.

Visible-Light-Induced Aerobic Oxidation of Benzylic C(sp 3)-H of Alkylarenes Promoted by DDQ, tert -Butyl Nitrite, and Acetic Acid

A visible-light photocatalytic aerobic oxidation of benzylic C(sp 3)-H bonds proceeded in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tert -butyl nitrite, and acetic acid. Advantages of this aerobic oxidation method include its relatively mild conditions, the use of visible-light irradiation instead of conventional thermal methods, the use of a low catalyst loading, and the ability to oxidize a range of alkylarenes, including xanthenes, thioxanthenes, and 9,10-dihydroacridines, to the corresponding ketones in excellent yields.