569-34-6

Basic information

• Product Name: 8-methoxycaffeine
• Synonyms: 8-Methoxycaffeine; 5-26-15-00080 (Beilstein Handbook Reference); 8-Methoxy-1,3,7-trimethylxanthine; BRN 0384756; Methoxycaffeine; NSC 8808; 1H-Purine-2,6-dione, 3,7-dihydro-8-methoxy-1,3,7-trimethyl- (9CI); Caffeine, 8-methoxy-; 8-methoxy-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
• CAS NO: 569-34-6
• Molecular Formula: C₉H₁₂N₄O₃
• Molecular Weight: 224.2166
• EINECS: 209-312-3
• Mol File: 569-34-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 395.3°C at 760 mmHg
• Flash Point: 192.8°C
• Density: 1.44g/cm³
• Vapor Pressure: 1.86E-06mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: 8-methoxycaffeine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methoxycaffeine(569-34-6)
• EPA Substance Registry System: 8-methoxycaffeine(569-34-6)

Safety Data

• Hazardous Substances Data: 569-34-6(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 13087-49-5 3,7-dimethyluric acid 
• 33868-03-0 1,7-dimethyluric acid 
• 5415-44-1 1,3,7-trimethyluric acid 
• 614-45-9 tert-Butyl peroxybenzoate 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 110-05-4 di-tert-butyl peroxide 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 2099-73-2 8-nitrotheophylline 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 612-37-3 7-methyluric acid 
• 69-93-2 uric Acid 
• 4921-49-7 8-chlorocaffeine 

Downstream Products

• 99765-16-9 3,4,5,7-Tetrahydro-8-methoxy-1,3,7-trimethyl-syn-10,anti-11-diphenyl-4,5-ethano-1H-purin-2,6-dion 
• 130272-00-3 8-Methoxy-3,4,5,7-tetrahydro-1,3,7-trimethyl-anti-10,syn-11-bis(4-chlorphenyl)-4,5-ethano-1H-purin-2,6-dion 
• 130168-08-0 8-Methoxy-3,4,5,7-tetrahydro-1,3,7-trimethyl-syn-10,anti-11-bis(4-chlorphenyl)-4,5-ethano-1H-purin-2,6-dion 
• 130272-01-4 3,4,5,7-Tetrahydro-1,3,7-trimethyl-anti-10,syn-11-bis(4-methoxyphenyl)-4,5-ethano-1H-purin-2,6,8(3H)-trion 
• 130168-09-1 3,4,5,7-Tetrahydro-1,3,7-trimethyl-syn-10,anti-11-bis(4-methoxyphenyl)-4,5-ethano-1H-purin-2,6,8(3H)-trion 
• 5415-44-1 1,3,7-trimethyluric acid 
• 130168-10-4 3,4,5,7-Tetrahydro-1,3,7-trimethyl-syn-10,anti-11-bis(4-chlorphenyl)-4,5-ethano-1H-purin-2,6,8(3H)-trion 
• 2309-49-1 theacrine 

Relevant articles and documents

Controlled C-5 methylation of caffeine by benzoyloxy radical addition at C-8

C-5 methylation of the model purine compound caffeine by acetyl benzoyl peroxide is the result of preferential addition of the electrophilic benzoyloxy radical at C-8 in neutral medium.X-ray structure and molecular orbital calculations on 1,3,5,7-tetramethyl-5,7-dihydrouric acid are presented.

Functionalization Including Fluorination of Caffeine, Guanosine Tetraacetate, and Uridine Triacetate using Electrochemical Oxidation

The title compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte.Caffeine afforded 8-fluorocaffeine as a sole product in 43percent yield.Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 7.3 and 4.8 percent yield, respectively.Similar electrochemical oxidation of caffeine with methanol, KCl or KCN yielded 8-methoxycaffeine, 8-chlorocaffeine, or 8-cyanocaffeine, respecticvely.

ADDITION OF ELECTROPHILIC RADICALS TO CAFFEINE: SYNTHETIC ASPECTS AND INFLUENCE OF THE PEROXIDIC INITIATORS

Primary and secondary electrophilic radicals such as: .CHRCO2CH3 (R=H, CH3, CO2CH3) and tertiary .CCl3 radical were added directly at C-8 of, th model purine compound, caffeine to give the corresponding 8-substituted derivatives in fairly good yields.Unexpected reaction of caffeine with oxy radicals from the initiators (PhCO2., t-BuOO.) gave rise to C-5 substituted 1,3,7-trimethyl-5,7-dihydrouric acid derivatives (C-5-R=CCl3, CH3, C(CH3)2CO2CH3) and to the spirodihydantoin C-8 adduct derivative of caffeine 11.