55085-47-7

Basic information

• Product Name: 5,6,7-Trimethoxycoumarin
• Synonyms: 5,6,7-Trimethoxycoumarin
• CAS NO: 55085-47-7
• Molecular Formula: C12H12O5
• Molecular Weight: 236.22
• Mol File: 55085-47-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 405.9°C at 760 mmHg
• Flash Point: 183.3°C
• Appearance: /
• Density: 1.249g/cm³
• Vapor Pressure: 8.46E-07mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: 5,6,7-Trimethoxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7-Trimethoxycoumarin(55085-47-7)
• EPA Substance Registry System: 5,6,7-Trimethoxycoumarin(55085-47-7)

Safety Data

• Hazardous Substances Data: 55085-47-7(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of coumarins that is coumarin substituted by methoxy groups at positions 5, 6 and 7.

InChI:InChI=1/C12H12O5/c1-14-9-6-8-7(4-5-10(13)17-8)11(15-2)12(9)16-3/h4-6H,1-3H3

Upstream product

• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 832-65-5 2-hydroxy-4,5,6-trimethoxybenzaldehyde 
• 4885-02-3 Dichloromethyl methyl ether 
• 642-71-7 3,4,5-trimethoxyphenol 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 17742-46-0 acetic acid 3,4,5-trimethoxy-phenyl ester 
• 292638-85-8 acrylic acid methyl ester 
• 486-28-2 fraxinol 
• 77-78-1 dimethyl sulfate 
• 28752-90-1 acetyl fraxinol 
• 32451-87-9 mandshurin 
• 623-47-2 propynoic acid ethyl ester 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 

Relevant articles and documents

Prenylcoumarins in One or Two Steps by a Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination/Cyclization Sequence

The one-pot synthesis of 8-prenylcoumarins from 1,1-dimethylallylated salicylaldehydes and the stabilized ylide [(ethoxycarbonyl)methylene]triphenylphosphorane under microwave conditions was found to have a limited scope. The sequence suffers from a difficult and sometimes low-yielding synthesis of the precursors and from a competing deprenylation upon microwave irradiation. This side reaction occurs in particular with electron rich arenes with two or more alkoxy groups at adjacent positions, a prominent substitution pattern in naturally occurring 8-prenylcoumarins. Both limitations of this one-step sequence were overcome by a two-step synthesis consisting of a microwave-promoted tandem allyl ether Claisen rearrangement/Wittig olefination and a subsequent olefin cross metathesis with 2-methyl-2-butene. The cross metathesis step proceeds with a high selectivity and yields exclusively the desired prenyl, rather than the alternative crotyl substituent. Several naturally occurring 8-prenylcoumarins that were previously inaccessible have been synthesized in good overall yields along this route.

Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C-H Bond Activation

An efficient annulation strategy involving the reaction of phenolic acetates with acrylates in the presence of [Rh2(OAc)4] as catalyst and formic acid as reducing agent, leading to the high yield synthesis of coumarin derivatives, has been developed. The addition of NaOAc as a base increased the yield of the products. The reaction is quite successful for both electron-rich as well as electron-deficient phenolic acetates, affording coumarins with excellent regioselectivity, and proceeds via C-H bond activation proven by deuterium incorporation studies.

Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins

The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction.