168759-60-2

Basic information

• Product Name: 7-bromo-4H-chromen-4-one
• Synonyms: 7-bromo-4H-chromen-4-one;4H-1-Benzopyran-4-one, 7-broMo-;7-Bromochromone
• CAS NO: 168759-60-2
• Molecular Formula: C₉H₅BrO₂
• Molecular Weight: 225.0388
• Mol File: 168759-60-2.mol

Chemical Properties

• Melting Point: 154-159°C
• Boiling Point: 306.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.688±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 7-bromo-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-bromo-4H-chromen-4-one(168759-60-2)
• EPA Substance Registry System: 7-bromo-4H-chromen-4-one(168759-60-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 168759-60-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
7-Bromo-4H-chromen-4-one is used as a building block in pharmaceutical research for the synthesis of biologically active compounds. Its unique structure and potential pharmacological activities make it a promising candidate for the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 7-Bromo-4H-chromen-4-one serves as a key intermediate for the preparation of various complex organic molecules. Its reactivity and functional group compatibility contribute to its utility in the synthesis of a wide range of compounds.
Used in Anticancer Applications:
7-Bromo-4H-chromen-4-one is used as an anticancer agent due to its potential to inhibit the growth and proliferation of cancer cells. Its pharmacological properties, such as anti-inflammatory and antimicrobial activities, may also contribute to its effectiveness in cancer treatment.
Used in Anti-inflammatory Applications:
7-Bromo-4H-chromen-4-one is used as an anti-inflammatory agent, leveraging its ability to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Antimicrobial Applications:
As an antimicrobial agent, 7-Bromo-4H-chromen-4-one is employed to combat microbial infections by inhibiting the growth of bacteria, fungi, and other microorganisms.
Used in Drug Discovery:
7-Bromo-4H-chromen-4-one is used in drug discovery efforts to identify novel compounds with therapeutic potential. Its diverse biological activities and structural features make it an attractive target for the development of new pharmaceuticals.

Upstream product

• 288067-35-6 4-bromo-2-hydroxy-benzonitrile 
• 30186-18-6 4'-bromo-2'-hydroxyacetophenone 
• 18386-03-3 3-(3-bromophenoxy)propionic acid 
• 591-20-8 3-Bromophenol 
• 1016736-70-1 3-(3-bromophenoxy)propanenitrile 

Downstream Products

• 1287312-22-4 7-(2-phenylethynyl)-4H-chromen-4-one 
• 1180671-95-7 (E,Z)-7-bromochroman-4-one O-tosyl oxime 
• 1180671-97-9 7-bromo-3-amino-chroman-4-one hydrochloride 
• 1260485-26-4 (E)-7-styrylchromone 
• 18442-22-3 7-Bromo-2,3-dihydro-4H-chromen-4-one 

Relevant articles and documents

Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides

A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.

CHROMANE-SUBSTITUED TETRACYCLIC COMPOUNDS AND USES THEREOF FOR TREATMENT OF VIRAL DISEASES

Disclosed are novel chromane-substituted tetracyclic compounds of Formula (I), and pharmaceutically acceptable salts thereof, wherein A, A', R2 R3, R4 and R5 are as defined in the description. Also disclosed are compositions comprising a chromane-substituted tetracyclic compound, and methods of using the chromane-substituted tetracyclic compounds for treating or preventing HCV infection in a patient.

Discovery of Chromane Containing Hepatitis C Virus (HCV) NS5A Inhibitors with Improved Potency against Resistance-Associated Variants

The discovery of potent and pan-genotypic HCV NS5A inhibitors faces many challenges including the significant diversity among genotypes, substantial potency shift conferred on some key resistance-associated variants, inconsistent SARs between different genotypes and mutants, and the lacking of models of inhibitor/protein complexes for rational inhibitor design. As part of ongoing efforts on HCV NS5A inhibition at Merck, we now describe the discovery of a novel series of chromane containing NS5A inhibitors. SAR studies around the "Z" group of the tetracyclic indole scaffold explored fused bicyclic rings as alternates to the phenyl group of elbasvir (1, MK-8742) and identified novel chromane and 2,3-dihydrobenzofuran derivatives as "Z" group replacements offered good potency across all genotypes. This effort, incorporating the C-1 fluoro substitution at the tetracyclic indole core, led to the discovery of a new series of NS5A inhibitors, such as compounds 14 and 25-28, with significantly improved potency against resistance-associated variants, such as GT2b, GT1a Y93H, and GT1a L31V. Compound 14 also showed reasonable PK exposures in preclinical species (rat and dog).

LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.

ANTIVIRAL COMPOUNDS

The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

Efficient synthesis of chromones with alkenyl functionalities by the heck reaction

The usefulness of the Heck reaction in the field of chromones has been demonstrated. Bromochromones with the halogen atom in their rings A and B were reacted with various terminal alkenes to give hitherto unknown alkenyl-substituted chromones. Reactivity of the substrates was found to markedly depend on the position of the bromine atom. Under phosphine-free conditions using a phase-transfer catalyst additive (tetrabutylammonium bromide), shorter reaction periods and usually higher yields were obtained.