82235-61-8

Basic information

• Product Name: ethyl 5,7-dimethoxy-2-oxo-2H-chromene-3-carboxylate
• Synonyms: 2H-1-Benzopyran-3-carboxylic acid, 5,7-dimethoxy-2-oxo-, ethyl ester
• CAS NO: 82235-61-8
• Molecular Formula: C₁₄H₁₄O₆
• Molecular Weight: 278.2574
• Mol File: 82235-61-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 455.8°C at 760 mmHg
• Flash Point: 204.7°C
• Density: 1.281g/cm³
• Vapor Pressure: 1.7E-08mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: ethyl 5,7-dimethoxy-2-oxo-2H-chromene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5,7-dimethoxy-2-oxo-2H-chromene-3-carboxylate(82235-61-8)
• EPA Substance Registry System: ethyl 5,7-dimethoxy-2-oxo-2H-chromene-3-carboxylate(82235-61-8)

Safety Data

• Hazardous Substances Data: 82235-61-8(Hazardous Substances Data)

Upstream product

• 708-76-9 2-hydroxy-4,6-dimethoxybenzaldehyde 
• 105-53-3 diethyl malonate 

Downstream Products

• 487-06-9 Limettin 
• 94068-62-9 2,2'-Dihydroxy-4,4',6,6'-tetramethoxy-benzaldazin 

Relevant articles and documents

The first total synthesis of (+/-)-linderol A, a tricyclic hexahydrodibenzofuran constituent of Lindera umbellata bark, with potent inhibitory activity on melanin biosynthesis of cultured B-16 melanoma cells.

[reaction in text] The first total synthesis of (+/-)-linderol A, a hexahydrodibenzofuran isolated from Lindera umbellata bark, with potent inhibitory activity on melanin biosynthesis of cultured B-16 melanoma cells was achieved via a 20-step of reaction

Nucleophilic addition reactions on 3-carbethoxy-5,7-dimethoxycoumarin

3-Carbethoxy-5,7-dimethoxycoumarin (2) underwent Michael addition and addition-cyclization of some active methylene compounds under different reaction conditions to give the adducts (3-7). Addition of phenylmagnesium bromide onto (2) yielded the tertiary alcohol (8). Addition of ammonia derivatives on (2) afforded the 3-carboxamides (9a-c) and azine (10). Furthermore, alcoholysis and hydrolysis yielded the coumarins (11a-c).

Reductions via Boranes: A New, Convenient Method for the Preparation of 3-Substituted Esters and Thioesters of 3,4-Dihydrocoumarin

Reduction of various O-ethyl coumarin-3-carboxylates and O-ethyl coumarin-3-thioncarboxylates with diborane, borane dimethyl sulfide, 9-borabicyclononane, and bisethane-diborane lead to the corresponding 3,4-dihydro derivatives with good yields.