6295-35-8

Basic information

• Product Name: 6-METHOXY-4-METHYLCOUMARIN
• Synonyms: 4-METHYL-6-METHOXYCOUMARIN;6-METHOXY-4-METHYLCOUMARIN;METHYL-6-METHOXYCOUMARINE, 4-;AURORA KA-3744
• CAS NO: 6295-35-8
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.2
• Mol File: 6295-35-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 163-167 °C(lit.)
• Boiling Point: 351.6 °C at 760 mmHg
• Flash Point: 146.3 °C
• Appearance: /
• Density: 1.195 g/cm³
• Vapor Pressure: 4.05E-05mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 6-METHOXY-4-METHYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-4-METHYLCOUMARIN(6295-35-8)
• EPA Substance Registry System: 6-METHOXY-4-METHYLCOUMARIN(6295-35-8)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 6295-35-8(Hazardous Substances Data)

Usage

General Description

6-Methoxy-4-methylcoumarin is a chemical compound with the formula C11H10O3. It is a derivative of coumarin, a natural substance found in many plants. 6-METHOXY-4-METHYLCOUMARIN is used in the pharmaceutical and cosmetic industries due to its potential antioxidant and anti-inflammatory properties. It is also utilized in the synthesis of various medications and as a fragrance in perfumes and other personal care products. Additionally, 6-methoxy-4-methylcoumarin has been studied for its potential role in cancer treatment, as it has shown promising anti-tumor activity in preliminary research. Overall, this compound has a range of potential applications and continues to be studied for its various biological effects.

InChI:InChI=1/C11H10O3/c1-7-5-11(12)14-10-4-3-8(13-2)6-9(7)10/h3-6H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 2373-31-1 6-hydroxy-4-methyl-chromen-2-one 
• 77-78-1 dimethyl sulfate 
• 4341-76-8 Ethyl 2-butynoate 
• 150-76-5 4-methoxy-phenol 
• 141-97-9 ethyl acetoacetate 
• 1205-91-0 benzene-1,4-diyl diacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 74-88-4 methyl iodide 
• 110450-38-9 p-methoxyphenyl but-2-ynoate 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 448212-00-8 (Z)-ethyl-3-(4,4,5,5)-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate 

Downstream Products

• 13522-86-6 2-iso-propyl-4-methoxyphenol 
• 65490-17-7 4-methoxy-2-(prop-1-en-2-yl)phenol 
• 1456809-26-9 (E)-3-(4-hydroxy-3,5-dimethylstyryl)-6-methoxy-4-methyl-2H-chromen-2-one 
• 1456809-40-7 (E)-6-methoxy-3-(4-((2-methoxyethoxy)methoxy)-3,5-dimethylstyryl)-4-methyl-2H-chromen-2-one 
• 1456809-28-1 (E)-6-hydroxy-3-(4-hydroxy-3,5-dimethylstyryl)-4-methyl-2H-chromen-2-one 
• 1456809-43-0 6-methoxy-3-((4-((2-methoxyethoxy)methoxy)-3,5-dimethylphenyl)ethynyl)-4-methyl-2H-chromen-2-one 
• 1456809-31-6 (E)-3-(4-hydroxy-3,5-dimethylstyryl)-7-methoxy-4-methyl-2H-chromen-2-one 
• 1456809-33-8 6-hydroxy-3-((4-hydroxy-3,5-dimethylphenyl)ethynyl)-4-methyl-2H-chromen-2-one 
• 95767-60-5 2-[(4-methyl-2-oxo-2H-chromen-6-yl)oxy]acetic acid 
• 2373-31-1 6-hydroxy-4-methyl-chromen-2-one 

Relevant articles and documents

Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons

Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.

B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions

Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]

Catalytic Activity of a Zr MOF Containing POCOP-Pd Pincer Complexes

A metal-organic framework assembled from POCOP-Pd pincer complex metallolinkers (1-PdBF4, Zr6O4(OH)4(L-PdMeCN)3(BF4)3, L = (2,6-(OPAr2)2C6H3, Ar = p-C6H4CO2-) has been generated via postsynthetic oxidative I-/BF4- ligand exchange with NOBF4. 1-PdBF4 catalyzes a range of organic transformations, including transfer hydrogenation of unsaturated organic substrates, terminal alkyne hydration, and intramolecular hydroarylation of alkynes. The homogeneous analogue, tBu4POCOP-PdBF4, shows poor catalytic activity for transfer hydrogenation and alkyne hydration and decomposes under the catalytic reaction conditions. Solubility limitations and catalyst deactivation pathways observed for the homogeneous pincer complex propound the advantages of using porous solid supports to immobilize organometallic species.