2555-23-9

Basic information

• Product Name: 7-hydroxy-4-methyl-3-phenyl-2H-chromen-2-one
• Synonyms: 2555-23-9; 7-Hydroxy-4-methyl-3-phenyl-2H-chromen-2-one
• CAS NO: 2555-23-9
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.2647
• Mol File: 2555-23-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 472.1°C at 760 mmHg
• Flash Point: 206.7°C
• Density: 1.289g/cm³
• Vapor Pressure: 1.55E-09mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 7-hydroxy-4-methyl-3-phenyl-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-hydroxy-4-methyl-3-phenyl-2H-chromen-2-one(2555-23-9)
• EPA Substance Registry System: 7-hydroxy-4-methyl-3-phenyl-2H-chromen-2-one(2555-23-9)

Safety Data

• Hazardous Substances Data: 2555-23-9(Hazardous Substances Data)

Upstream product

• 112030-33-8 4-methyl-3-phenyl-7-phenylacetoxy coumarin 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 
• 63577-89-9 ethyl 2-phenyl-2,3-butadienoate 
• 108-46-3 recorcinol 
• 103-82-2 phenylacetic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 4468-48-8 1-phenyl-1-cyanopropan-2-one 
• 114-70-5 sodium phenylacetate 
• 103-80-0 phenylacetyl chloride 
• 5413-05-8 ethyl 2-phenylacetoacetate 
• 75200-57-6 7-acetoxy-4-methyl-3-phenyl-2H-1-benzopyran-2-one 
• 100-34-5 benzene diazonium chloride 

Downstream Products

• 23028-24-2 7-methoxy-4-methyl-3-phenylcoumarin 
• 672938-11-3 8-bromo-7-hydroxy-4-methyl-3-phenyl-coumarin 
• 212694-37-6 6-bromo-7-hydroxy-4-methyl-3-phenyl-coumarin 
• 873403-43-1 6,8-dibromo-7-hydroxy-4-methyl-3-phenyl-coumarin 
• 866887-44-7 7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-4-methyl-3-phenyl-2H-chromen-2-one 
• 42308-38-3 3-(2,4-dimethoxy-phenyl)-2-phenyl-crotonic acid 
• 75200-67-8 5-Methyl-3-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-2,6-diphenyl-furo[3,2-g]chromen-7-one 
• 75200-70-3 5-Methyl-2,6-diphenyl-3-[4-(2-piperazin-1-yl-ethoxy)-phenyl]-furo[3,2-g]chromen-7-one 
• 75200-63-4 5-Methyl-2,6-diphenyl-3-[4-(3-piperidin-1-yl-propoxy)-phenyl]-furo[3,2-g]chromen-7-one 
• 75200-68-9 5-Methyl-2,6-diphenyl-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-furo[3,2-g]chromen-7-one 
• 75200-69-0 5-Methyl-2,6-diphenyl-3-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-furo[3,2-g]chromen-7-one 
• 75200-65-6 3-[4-(2-Diethylamino-ethoxy)-phenyl]-5-methyl-2,6-diphenyl-furo[3,2-g]chromen-7-one 
• 75200-66-7 3-[4-(2-Dimethylamino-ethoxy)-phenyl]-5-methyl-2,6-diphenyl-furo[3,2-g]chromen-7-one 
• 75200-61-2 2,6-Diphenyl-3-(p-methoxyphenyl)-5-methyl-7-oxo-7H-furo<3,2-g><1>benzopyran 

Relevant articles and documents

1,2,3,4-Tetrahydroisoquinoline/2H-chromen-2-one conjugates as nanomolar P-glycoprotein inhibitors: Molecular determinants for affinity and selectivity over multidrug resistance associated protein 1

A series of coniugates bearing a 1,2,3,4-tetrahydroisoquinoline motif linked to substituted 7-hydroxy-2H-chromen-2-ones was synthesized and assayed through calcein-AM test in Madin-Darby Canine Kidney (MDCK) cells overexpressing P-glycoprotein (P-gp) and closely related multidrug resistance associated protein 1 (MRP1) to probe the interference with efflux mechanisms mediated by P-gp and MRP1, respectively. A number of substituents at C3 and C4 of coumarin nucleus along with differently sized and shaped spacers was enrolled to investigate the effects of focused structural modifications over affinity and selectivity. Linker length and flexibility played a key role in enhancing P-gp affinity as proved by the most potent P-gp modulator (3h, IC50 = 70 nM). A phenyl ring within the spacer (3k, 3l, 3o) and bulkier groups (Br in 3r, Ph in 3u) at coumarin C3 led to derivatives showing nanomolar activity (160 nM 50 350). Molecular docking calculations carried out on a human MDR1 homology model structure contributed to gain insights into the ligands’ binding modes. Some compounds (3d, 3h, 3l, 3r, 3t, 3u) reversed MDR thereby restoring doxorubicin cytotoxicity when co-administered with the drug into MDCK-MDR1 cells.

Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts

This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is

Regioselective C-3 arylation of coumarins with arylhydrazines via radical oxidation by potassium permanganate

An efficient protocol for oxidative C-3 arylation of coumarins with arylhydrazine has been developed using potassium permanganate as an oxidant. The arylated coumarins with different electronic properties were obtained in moderate to good yields. The deve