17372-53-1

Basic information

• Product Name: 6-METHOXYCOUMARIN
• Synonyms: 6-METHOXYCOUMARIN;6-METHOXY-2H-CHROMEN-2-ONE;6-Methoxy-2H-chromen-2-one 97%
• CAS NO: 17372-53-1
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• Product Categories: Coumarins;Fused Ring Systems
• Mol File: 17372-53-1.mol
• Article Data: 33

Chemical Properties

• Melting Point: 189-191 °C
• Boiling Point: 348.2 °C at 760 mmHg
• Flash Point: 144.7 °C
• Appearance: /
• Density: 1.248 g/cm³
• Vapor Pressure: 5.12E-05mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: 6-METHOXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXYCOUMARIN(17372-53-1)
• EPA Substance Registry System: 6-METHOXYCOUMARIN(17372-53-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 17372-53-1(Hazardous Substances Data)

Usage

General Description

6-Methoxycoumarin, also known as 6-methoxy-2H-1-benzopyran-2-one, is a chemical compound belonging to the coumarin family. It is a naturally occurring compound found in various plant species and has been isolated from the seeds and roots of different plants. 6-Methoxycoumaring has been studied for its potential biological activities, including anti-inflammatory, antioxidant, and anticancer properties. It has also been used as a starting material in the synthesis of pharmaceuticals and agrochemicals. The compound has a unique chemical structure, characterized by a benzopyran ring with a methoxy group attached at the 6-position, which contributes to its diverse biological activities and potential applications in various fields.

InChI:InChI=1/C10H8O3/c1-12-8-3-4-9-7(6-8)2-5-10(11)13-9/h2-6H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 6093-68-1 6-hydroxycoumarin 
• 74-88-4 methyl iodide 
• 105786-73-0 3-Ethoxyacrylsaeure-4-methoxyphenylester 
• 62536-85-0 2-acetoxy-5-methoxybenzaldehyde 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 150-76-5 4-methoxy-phenol 
• 623-47-2 propynoic acid ethyl ester 
• 471-25-0 Propiolic acid 
• 90920-97-1 4-methoxyphenyl propynoate 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 927-80-0 1-ethoxyacetylene 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 5683-31-8 3-(trimethylsilyl)prop-2-ynoic acid 

Downstream Products

• 20920-98-3 6-methoxy-3,4-dihydrocoumarin 
• 40546-95-0 3,4-dihydro-6-methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 1462914-07-3 C₁₈H₁₃NO₅ 
• 1462914-09-5 C₁₈H₁₃NO₅ 
• 1462914-00-6 C₁₉H₁₆O₄ 
• 1462914-03-9 C₁₉H₁₆O₄ 
• 1462913-93-4 C₁₈H₁₄O₃ 
• 6468-48-0 6-Methoxy-3-phenyl-coumarin 
• 40547-03-3 6-Methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 10538-49-5 3-(2,5-dimethoxyphenyl)propanoic acid 
• 225791-33-3 2-hydroxy-5-methoxybenzenepropanoic acid 
• 38489-78-0 (E)-2-hydroxy-5-methoxycinnamic acid 
• 22927-97-5 6-methoxy-2,2-dimethyl-2H-chromene 

Relevant articles and documents

A practical one-pot synthesis of coumarins in aqueous sodium bicarbonate via intramolecular Wittig reaction at room temperature

An efficient, simple and relatively inexpensive method for the synthesis of coumarins in aqueous sodium bicarbonate at ambient temperature has been developed. It features an intramolecular Wittig reaction of substituted 2-formylphenyl 2-bromoacetate in saturated aqueous sodium bicarbonate. Its advantages include benign reaction conditions, easy work-up and good overall yield with short reaction time. Various substituted coumarins have been synthesized by utilizing this methodology. This journal is

Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins

Cu-catalyzed A3 coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields.

Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids

A facile Fe(III)-catalyzed oxidative decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with coumarins has been developed. This transformation, which provides a series of C-3 difluoroarylmethylated coumarins containing various functional groups in moderate-to-good yields, features easily accessible starting materials and operational simplicity.

Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides

A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.