13130-21-7

Basic information

• Product Name: 3-(2-Hydroxyphenyl)coumarin
• Synonyms: 3-(2-Hydroxyphenyl)-2H-1-benzopyran-2-one;3-(2-Hydroxyphenyl)coumarin
• CAS NO: 13130-21-7
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• Mol File: 13130-21-7.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(2-Hydroxyphenyl)coumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Hydroxyphenyl)coumarin(13130-21-7)
• EPA Substance Registry System: 3-(2-Hydroxyphenyl)coumarin(13130-21-7)

Safety Data

• Hazardous Substances Data: 13130-21-7(Hazardous Substances Data)

Upstream product

• 90-02-8 salicylaldehyde 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 955-10-2 3-phenylcumarin 
• 164170-38-1 2'-(2-benzyloxybenzoyloxy)acetophenone 
• 118-93-4 o-hydroxyacetophenone 
• 4349-62-6 2-benzyloxybenzoyl chloride 
• 14389-86-7 2-benzyloxybenzoic acid 
• 55142-16-0 methyl 2-(benzyloxy)benzoate 
• 119-36-8 methyl salicylate 
• 69-72-7 salicylic acid 
• 1441-87-8 salicyloyl chloride 
• 145723-30-4 2-(2-Hydroxybenzoyloxy)acetophenone 
• 100-66-3 methoxybenzene 
• 7035-02-1 o-Methoxybenzyl chloride 

Downstream Products

• 18221-50-6 dihydroxy-stilbene 
• 13130-34-2 3-(2-acetoxy-phenyl)-coumarin 

Relevant articles and documents

Palladium-Catalyzed Weakly Coordinating Lactone-Directed C-H Bond Functionalization of 3-Arylcoumarins: Synthesis of Bioactive Coumestan Derivatives

A palladium-catalyzed highly regioselective ortho-selective C-H functionalization of 3-arylcoumarins has been developed. The method utilizes the weakly coordinating lactone as a directing group. The versatility of the strategy is highlighted by developing methodologies for alkenylation, halogenation, fluoroalkoxylation, and hydroxylation. Different functional groups were well tolerated, and functionalized coumarins were obtained in moderate to high yields. The method also showed good selectivity for monofunctionalization versus difunctionalization. The generated ortho-hydroxy derivatives were cyclized in the presence of DDQ, thus developing a simple and fast method for the synthesis of bioactive coumestan from 3-arylcoumarins.

Metal-free Synthesis of Spiro-2,2′-benzo[b]furan-3,3′-ones via PhI(OAc)2-Mediated Cascade Spirocyclization

Treating the benzyl protected 3-hydroxy-1,3-bis(2-hydroxyphenyl)prop-2-en-1-ones solely with PhI(OAc)2 (PIDA) in DCE at room temperature readily furnished the seldom studied spiro-2,2′-benzo[b]furan-3,3′-ones in satisfactory to excellent yields. The hypervalent iodine reagent enables the metal-free cascade spirocyclization resulting in the dual oxidative C?O bond formation. (Figure presented.).

Ru(II)-Catalyzed Site-Selective Hydroxylation of Flavone and Chromone Derivatives: The Importance of the 5-Hydroxyl Motif for the Inhibition of Aurora Kinases

An efficient protocol for Ru(II)-catalyzed direct C-H oxygenation of a broad range of flavone and chromone substrates was developed. This convenient and powerful synthetic tool allows for the rapid installation of the hydroxyl group into the flavone, chromone, and other related scaffolds and opens the way for analog synthesis of highly potent Aurora kinase inhibitors. The molecular docking simulations indicate that the formation of bidentate H-bonding patterns in the hinge regions between the 5-hydroxyflavonoids and Ala213 was the significant binding force, which is consistent with experimental and computational findings.