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

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 Short Synthesis of Delavatine A Unveils New Insights into Site-Selective Cross-Coupling of 3,5-Dibromo-2-pyrone

The recognition of latent symmetry in delavatine A has enabled a short synthesis of the natural product starting from 3,5-dibromo-2-pyrone. The concise synthetic route features a cascade process involving a 6p electrocyclization to construct the indane co

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.

Regioselectivity in the Stille Coupling Reactions of 3,5-Dibromo-2-pyrone

The Stille couplings of 3,5-dibromo-2-pyrone normally take place regioselectively at C3, lower in electron density than C5, thus oxidative addition proceeds faster . When the reactions are carried out with Cu(I) in DMF or other polar aprotic solvent, however, the couplings occur predominantly at C5. The observed regiochemical reversal is attributed to the preferred formation of 5-pallado-2-pyrone intermediate which, in addition, turned out to be more reactive than 3-pallado-2-pyrone intermediate. Copyright

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.