84-99-1

Basic information

• Product Name: Xanthoxyletin
• Synonyms: Xanthoxyletin;5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one;Xanthoxylin N;Xanthoxyloin;5-methoxy-8,8-dimethyl-pyrano[3,2-g]chromen-2-one;5-methoxy-8,8-dimethylpyrano[3,2-g]chromen-2-one;NSC 35542
• CAS NO: 84-99-1
• Molecular Formula: C13H12O2Sn
• Molecular Weight: 318.94318
• Mol File: 84-99-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 134-135℃ (ethanol )
• Boiling Point: 321.52°C (rough estimate)
• Flash Point: 197.2°C
• Appearance: /
• Density: 1.1178 (rough estimate)
• Vapor Pressure: 6.81E-08mmHg at 25°C
• Refractive Index: 1.4300 (estimate)
• CAS DataBase Reference: Xanthoxyletin(CAS DataBase Reference)
• NIST Chemistry Reference: Xanthoxyletin(84-99-1)
• EPA Substance Registry System: Xanthoxyletin(84-99-1)

Safety Data

• Hazardous Substances Data: 84-99-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3

Upstream product

• 87702-68-9 5-hydroxy-xanthyletin 
• 74-88-4 methyl iodide 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 17053-75-7 dihydroxanthoxyletin 
• 31525-75-4 5-hydroxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 343228-39-7 7-(1,1-dimethyl-2-propynyloxy)-8-iodo-5-methoxycoumatin 
• 76256-29-6 5,7-diacetoxy-8-(3'-methyl-2'-butenyl)coumarin 
• 53017-21-3 5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one 
• 74794-29-9 7-hydroxy-8-iodo-5-methoxychromene-2-one 
• 3067-10-5 7-hydroxy-5-methoxychromene-2-one 
• 676529-26-3 toluene-4-sulfonic acid 5-hydroxy-2,2-dimethyl-4-oxo-chroman-7-yl ester 
• 54416-00-1 toluene-4-sulfonic acid 5-methoxy-2,2-dimethyl-chroman-7-yl ester 
• 541-47-9 3-Methylbutenoic acid 
• 50386-17-9 3,4-Dihydro-7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran 

Downstream Products

• 3067-09-2 6-formyl-7-hydroxy-5-methoxycoumarin 
• 110336-04-4 7-hydroxy-5-methoxy-6-(phenylhydrazono-methyl)-coumarin 

Relevant articles and documents

Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion

A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.

CLAISEN REARRANGEMENTS-XII SYNHESIS OF THE COUMARINS, 5-METHOXYSESELIN, TRACHYPHYLLIN, COUMURRAYIN AND XANTHOXYLETIN

The structure of the natural coumarins, 5-methoxyseselin 7 and trachyphyllin 14 have been confirmed by total syntheses from 7-acetoxy-5-prenyloxycoumarin 1 in good overall yields.Convenient synthetic routes to the natural coumarins, coumurrayin 4 and xanthoxyletin 10 have also been established.

Synthesis of Linear Pyranocoumarins: Xanthoxyletin, 4-Methylxanthyletin, and 4-Phenylxanthyletin

A convenient synthesis of linear pyranocoumarins (2H,8H-benzodipyran-2-ones), viz., xanthoxyletin, 4-methylxanthyletin and 4-phenylxanthyletin is described which uses blocking the 8-position of appropriate 7-hydroxycoumarin derivatives with iodine and 1,1-dimethyl-2-propynylation followed by cyclisation.