508234-56-8

Basic information

• Product Name: 3-bromo-5-phenylpyran-2-one
• Synonyms: 3-bromo-5-phenylpyran-2-one
• CAS NO: 508234-56-8
• Molecular Weight: 251.079
• Mol File: 508234-56-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 356.7±42.0 °C(Predicted)
• Density: 1.618±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3-bromo-5-phenylpyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-5-phenylpyran-2-one(508234-56-8)
• EPA Substance Registry System: 3-bromo-5-phenylpyran-2-one(508234-56-8)

Safety Data

• Hazardous Substances Data: 508234-56-8(Hazardous Substances Data)

Upstream product

• 960-16-7 tributylphenylstannane 
• 19978-41-7 3,5-dibromo-2H-pyran-2-one 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

A Unified Strategy for the Enantiospecific Total Synthesis of Delavatine A and Formal Synthesis of Incarviatone A

We describe a symmetry-inspired synthetic approach that has enabled a short synthesis of delavatine A and a formal synthesis of incarviatone A, which are two likely biosynthetically related natural products. The indane core of these natural products was constructed through a cascade sequence involving five transformations that occur in a single pot. Leveraging symmetry has allowed us to trace both natural products back to a versatile building block, 3,5-dibromo-2-pyrone, and studies related to site-selective cross-coupling of this polyhalogenated heterocycle are described. In addition, our strategy gave access to a putative biogenetic precursor, from which the syntheses of both natural products were attempted.

Regiocontrolled Suzuki-Miyaura couplings of 3,5-dibromo-2-pyrone

In a similar way to its Stille coupling reactions, 3,5-di-bromo-2-pyrone undergoes the Suzuki-Miyaura coupling reactions at either the C3- or the C5-position with high regioselectivity depending on the reaction conditions.

Regioselective Stille coupling reactions of 3,5-dibromo-2-pyrone with various aryl and vinyl stannanes

3,5-Dibromo-2-pyrone underwent facile regioselective Stille coupling reactions with aryl, heteroaryl and vinyl stannanes to produce various 3-substituted, 5-bromo-2-pyrones. Addition of a catalytic amount of CuI greatly increased the selectivity and chemical yield of the desired 3-aryl-5-bromo-2-pyrone. Second Stille coupling reactions on the resulting 3-aryl-2-pyrones gave rise to a series of potentially useful 2-pyrones with two different functionalities at C3 and C5 position in good to excellent isolated yields. 2-Pyrones with pyridyl groups at C3 position can undergo Lewis acid catalyzed Diels-Alder cycloaddition reactions with benzyl vinyl ether.