6724-42-1

Basic information

• Product Name: 8-Formyl-7-methoxycoumarin
• Synonyms: 7-Methoxy-8-formylcoumarin;8-Formyl-7-methoxycoumarin;Paniculal;7-methoxy-2-oxo-2H-chromene-8-carbaldehyde
• CAS NO: 6724-42-1
• Molecular Formula: C11H8O4
• Molecular Weight: 204
• Mol File: 6724-42-1.mol

Chemical Properties

• Melting Point: 208-209℃
• Boiling Point: 424℃
• Flash Point: 194℃
• Appearance: /
• Density: 1.336
• CAS DataBase Reference: 8-Formyl-7-methoxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Formyl-7-methoxycoumarin(6724-42-1)
• EPA Substance Registry System: 8-Formyl-7-methoxycoumarin(6724-42-1)

Safety Data

• Hazardous Substances Data: 6724-42-1(Hazardous Substances Data)

Upstream product

• 4394-85-8 4-morpholinecarboxaldehyde 
• 65763-01-1 7-methoxy-8-iodo-2H-chromen-2-one 
• 10387-49-2 7-acetyloxycoumarin 
• 2067-86-9 8-formyl-7-hydroxycoumarin 
• 74-88-4 methyl iodide 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 65763-00-0 7-hydroxy-8-iodocoumarin 
• 6545-99-9 Phebalosin 
• 124988-29-0 murrangatin 

Downstream Products

• 6545-99-9 8-(3-isopropenyloxiran-2-yl)-7-methoxy-2H-chromen-2-one 

Relevant articles and documents

Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF3for (E)-Vinyl Trifluoromethyl Thioethers

An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct Cvinyl-SCF3 bonds with stable AgSCF3 as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

A route to the structure proposed for puetuberosanol and approaches to the natural products marshrin and phebalosin

Synthesis of the structure claimed for puetuberosanol 1 (using the Juliá-Colonna oxidation in a key step) showed that the natural product was a different material. The isomeric epoxy alcohols 16-18 can be discounted from the alternatives. An analogue 19 of marshrin 2 was prepared but the synthesis of the natural product was thwarted by failure of a Juliá-Colonna oxidation in the key step. The epoxy ketone 29 was prepared by Darzens condensation and was converted into (±)-phebalosin 3.

Studies on Rutaceae: Part VI - Reacrtions and Rearrangements of Coumarins

Interesting reactions and rearrangements of isoprenoid systems have been observed in naturally occuring compounds like 6-(3',4'-epoxy-3'-methyl-γ-butyrolactonyl)-7-methoxycoumarin (micromelumin) (1), 7-methoxy-8-(1',2'-epoxy-3'-methylbut-3'-enyl)coumarin (phebalosin) (2), 7-methoxy-8-(2'-hydroxy-3'-methylbut-3'-enyl)coumarin (auraptenol) (3) and 7-methoxy-8-(3'-methylbut-2'-enyl)coumarin (osthol) (4).These reactions/rearrangements have led to the synthesis of coumarins already isolated from nature.Micromelumin (1) with pyridinium chloride affords the naturally occuring angelical (5), 6-(3'-methyl-3'-chloro-4'-hydroxy-γ-butyrolactonyl)- 7-methoxycoumarin (6b), 7-methoxycoumarinyl-6-tetronic acid derivative (7) and 6-(1'-carboxy-2'-methyl-3',4'-dihydroxybutenyl)-7-methoxycoumarin (8).Phebalosin (2) has been used for the hemisynthesis of the two naturally occuring diastereoisomeric coumarins minumicrolin (9) and murrangatin (10).Osthol (4) and auraptenol (3) have been used for the synthesis of the naturally occuring arnottinin (14)

ACID REARRANGEMENTS OF THE MURRANGATINS

Acid-catalyzed rearrangements of threo- murrangatin gave coumarins with tetrahydrofuryl side-chains, differences in reactivity from the erythro- isomer being attributed to stereoelectronic control.