132559-91-2

Basic information

• Product Name: 4-Bromo-6-Methyl-2H-Pyran-2-One
• Synonyms: 4-Bromo-6-Methyl-2H-Pyran-2-One;2H-Pyran-2-one, 4-bromo-6-methyl-;4-bromo-6-methyl-2(2H)-pyranone;4-Bromo-6-Methyl-2H-Pyran-2-One(WXC01361)
• CAS NO: 132559-91-2
• Molecular Formula: C₆H₅BrO₂
• Molecular Weight: 189.0067
• Mol File: 132559-91-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-Bromo-6-Methyl-2H-Pyran-2-One(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-6-Methyl-2H-Pyran-2-One(132559-91-2)
• EPA Substance Registry System: 4-Bromo-6-Methyl-2H-Pyran-2-One(132559-91-2)

Safety Data

• Hazardous Substances Data: 132559-91-2(Hazardous Substances Data)

Upstream product

• 675-10-5 4-hydroxy-6-methyl-2-pyron 

Downstream Products

• 505097-72-3 1-(6-methyl-2-oxo-2H-pyran-4-yl)-pyrrolidine-2-carboxylic acid methoxy-methyl-amide 
• 811862-80-3 4-(4-fluorophenyl)-6-methyl-2H-pyran-2-one 
• 4467-33-8 6-methyl-4-phenyl-2H-pyran-2-one 
• 186032-77-9 6-methyl-4-(phenylethynyl)pyran-2-one 
• 67075-01-8 4-(4-methoxy-phenyl)-6-methyl-pyran-2-one 

Relevant articles and documents

Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines.

Bioactive synthetic 4-substituted-6-methyl-2-pyrones are reported. Various 4-substitutents have been incorporated using Pd-catalysed carbon-carbon bond coupling procedures. Preliminary screening of the 2-pyrones against human ovarian carcinoma (A2780) and

An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone

We herein report the efficient syntheses of biologically active 4-alkenyl- and 4-alkynyl-6-methyl-2-pyrones using Pd-catalysed coupling procedures. A palladium on carbon/triphenylphosphine combination is shown to be the most effective catalyst for Sonogas

PI3K INHIBITORS AND USES THEREOF

The development of a new, targeted drug delivery paradigm coupled to improved PI3K inhibitors (e.g., PI3Kα inhibitors) represents a significant advance in cancer therapy. Provided herein are compounds, such as compounds of Formula (I) and (II), and pharmaceutically acceptable salts, hydrates, solvates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof. The compounds provided herein are PI3K (e.g., PI3Kα) inhibitors and are therefore useful for the treatment and/or prevention of various diseases (e.g., proliferative diseases such as cancer). Also provided herein are nanoparticles and nanogels (e.g., P-selectin targeting nanoparticles) comprising PI3K inhibitors, such a compound described herein. In certain embodiments, a nanoparticle or nanogel described herein encapsulates a compound described herein for targeting delivery to cancer cells or tumors.

Unexpected C-N bond formation via Smiles rearrangement: One pot synthesis of N -arylated coumarin/pyran derivatives

A conceptually new and one-pot method for the synthesis of N-arylated coumarin/pyran derivatives via Smiles rearrangement. The reaction of 4-bromocoumarin/pyran with 2-amino phenols affords O-arylated coumarin/pyran which subsequently rearranges into N-arylated coumarin/pyran under mild reaction conditions in good yields.

Synthesis of trifluoromethylthiolated and trifluoromethylselenolated pyrones

Trifluoromethylthiolation and trifluoromethylselenolation of 3- or 4-iodo(bromo)-2-pyrones with (bpy)CuSCF3 and [(bpy)CuSeCF3]2 provide a convenient method for the synthesis of trifluoromethylthio(seleno)lated 4-alkoxy-, aryloxy-, and benzyloxy-2-pyrones in high yields.

Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation

Aryl-heteroaryl coupling via double C-H activation is a powerful transformation that avoids the installation of activating groups. A double C-H activation of privileged biological scaffolds, 2-coumarins and 2-pyrones, is reported. Despite the rich chemistry of these molecular frameworks, the yields are very good. Excellent regioselectivity was achieved on the pyrones. This methodology was applied to the synthesis of flemichapparin C in three steps. Isotope effect experiments were carried out, and a mechanism is proposed.

Intramolecular Direct Arylation of 3-Halo-2-pyrones and 2-Coumarins

Direct arylation represents a favorable alternative to traditional cross-coupling and has found widespread use with simple aryls and robust heterocycles. Herein a direct arylation protocol has been optimized and applied to 2-pyrones, which are delicate an

Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling

α-Pyrones and pyrimidones are common structural motifs in natural products and bioactive compounds. They also display photochemistry that generates high-energy intermediates that may be capable of protein reactivity. A library of pyrones and pyrimidones was synthesized, and their potential to act as photoaffinity probes for nondirected affinity-based protein profiling in several crude cell lysates was evaluated. Further "proof-of-principle" experiments demonstrate that a pyrimidone tag on an appropriate scaffold is equally capable of proteome labeling as a benzophenone.

An economical access to 3,4-diaryl-2(5H)-furanones and 4-aryl-6-methyl- 2(2H)-pyranones by pd-catalyzed Suzuki-type arylation of 3-aryl-4-tosyloxy-2(5H) -furanones and 6-methyl-4-tosyloxy-2(2H)-pyranones, respectively

Both symmetrical and unsymmetrical 3,4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosy

ANTIBACTERIAL CONDENSED THIAZOLES

Compound of formula (I) have antibacterial activity: wherein: m is 0 or 1; Q is hydrogen or cyclopropyl; AIk - is an optionally substituted, divalent C1-C6 alkylene, alkenylene or alkynylene radical which may contain an ether (-0-), thioether (-S-) or amino (-NR)- link, wherein R is hydrogen, -CN or C1-C3 alky!; X is -C(=O)NR6-, or -C(=O)O- wherein R6 is hydrogen, optionally substituted C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl; Z1 is -N= or -CH= Z2 is -N= or -C(R1)=; R1 is hydrogen, methyl, ethyl, ethenyl, ethynyl, methoxy, mercapto, mercaptomethyl halo, fully or partially fluorinated (C1-C2)alkyl, (C1-C2JaIkOXy or (C1-C2)alkylthio, nitro, or nitrile (-CN); R2 is a group Q1 -[Alk1]q-Q2 -, wherein q is 0 or 1; AIkl is an optionally substituted, divalent, straight chain or branched C1-C6 alkylene, or C2-C6 alkenylene or C2-C6 alkynylene radical which may contain or terminate in an ether (-O-), thioether (-S-) or amino (-NR)- link; Q2 is an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 5 or 6 ring atoms or an optionally substituted divalent bicyclic carbocyclic or heterocyclic radical having 9 or 10 ring atoms; Q1 is hydrogen, an optional substituent or an optionally substituted carbocyclic or heterocyclic radical having 3-7 ring atoms