5631-75-4

Basic information

• Product Name: 2-Methyl-2,3-dihydro-4H-1-benzopyran-4-one
• Synonyms: 2,3-Dihydro-2-methyl-4H-1-benzopyran-4-one;2-Methyl-2,3-dihydro-4H-1-benzopyran-4-one;2-methylchroman-4-one
• CAS NO: 5631-75-4
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 5631-75-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Methyl-2,3-dihydro-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-2,3-dihydro-4H-1-benzopyran-4-one(5631-75-4)
• EPA Substance Registry System: 2-Methyl-2,3-dihydro-4H-1-benzopyran-4-one(5631-75-4)

Safety Data

• Hazardous Substances Data: 5631-75-4(Hazardous Substances Data)

Upstream product

• 5751-48-4 2-methylchromone 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 64-17-5 ethanol 
• 46117-36-6 but-3-enoic acid phenyl ester 

Downstream Products

• 129410-09-9 2,3-dihydro-2-methyl-4H-1-benzopyran-4-one 2,4-dinitrophenylhydrazone 
• 5751-48-4 2-methylchromone 
• 62756-35-8 2,3-dihydro-2-methyl-2-phenyl-4H-1-benzopyran-4-one 

Relevant articles and documents

A Borane-Catalyzed Metal-Free Hydrosilylation of Chromones and Flavones

A Piers-type hydrosilylation of chromones and flavones has been successfully realized for the first time using 0.1 mol % of borane catalyst generated in situ by hydroboration of pentafluorostyrene with HB(C 6 F 5) 2 to afford a variety of chromanones and flavanones in 60-99% yields. An attempt for the asymmetric transformation with chiral diyne and HB(C 6 F 5) 2 gave chromanones and flavanones in high yields with up to 32% ee.

3-Hydroxy-(4H)-benzopyran-4-ones as potential iron chelating agents in vivo

Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalised from specific carriers or intracellular sites (inflammation, eurodegenerative diseases, post-ischaemic reperfusion, etc.). In order to be used for therapeutical purposes in vivo, a reliable iron chelator should be capable of preventing the undesired effects that follow the electrochemical activation of iron (see below). Bearing in mind the molecular structure of some flavonols that are able to chelate iron, we synthesised a new oral iron-chelator, 2-methyl-3-hydroxy-4H-benzopyran-4-one (MCOH). We demonstrate that MCOH chelates iron in a 2:1 ratio showing a stability constant of ～1010. MCOH is able to cross cell membranes (erythrocytes, ascite tumour cells) in both directions. Following intraperitoneal administratio to rats, it is quickly taken up by the liver and excreted in the urine withi 24 h. A similar behaviour has bee documented after oral administration. We propose that MCOH may represent the prototype of a new class of iron chelating agents to be developed for iron-removal therapy in vivo with the goal of preventing tissue damage caused by the iron redox cycle. Copyright

Cobalt schiff base complex promoted retro-claisen reaction of 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanediones and flavone formation

Co(salpr) promotes the conversion of 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanediones to retro-Claisen reaction products and flavones in methanol under oxygen. Base catalysis by Co(salpr)(OH) produced in situ is responsible for the reaction.