79953-00-7

Basic information

• Product Name: 8-(phenylazo)guanine
• Synonyms: 8-(phenylazo)guanine
• CAS NO: 79953-00-7
• Molecular Formula: C₁₁H₉N₇O
• Molecular Weight: 0
• Mol File: 79953-00-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 425.9°C at 760 mmHg
• Flash Point: 211.4°C
• Appearance: /
• Density: 1.74g/cm³
• Vapor Pressure: 1.85E-07mmHg at 25°C
• Refractive Index: 1.872
• CAS DataBase Reference: 8-(phenylazo)guanine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(phenylazo)guanine(79953-00-7)
• EPA Substance Registry System: 8-(phenylazo)guanine(79953-00-7)

Safety Data

• Hazardous Substances Data: 79953-00-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H9N7O/c12-10-14-8-7(9(19)16-10)13-11(15-8)18-17-6-4-2-1-3-5-6/h1-5,17H,(H3,12,14,15,16,18,19)

Upstream product

• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 60285-31-6 N,N'-diphenyl-N-nitroso-urea 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 58550-48-4 1-nitroso-1-phenyl-3-(3-pyridylmethyl)urea 
• 369-58-4 benzenediazonium hexafluorophosphate 
• 53101-95-4 1-phenyl-3-pyridin-3-ylmethylurea 
• 62-53-3 aniline 

Downstream Products

• 168701-75-5 8-phenylazoguanosine 

Relevant articles and documents

Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct in DNA

1-(Phenylazo)-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) is a liver and urinary bladder carcinogen in mammals. Sudan I forms benzenediazonium ion during cytochrome P-450 catalyzed metabolism. Calf thymus DNA was reacted with Sudan I activated by microsomal enzymes or with benzenediazonium ion in vitro, and the adducts formed were analyzed by the 32P-postlabeling technique. Both enrichment procedures (1-butanol extraction and nuclease P1 digestion) of this technique were employed for detection and quantitation of the DNA adducts formed. Cochromatographic analyses of adduct spots obtained by reaction with DNA or homopolydeoxyribonucleotides showed that the major Sudan I-DNA adduct was formed with deoxyguanosine. This adduct was also found in DNA directly reacted with benzenediazonium ion. The major Sudan I-DNA adduct was characterized by UV/vis absorbance spectroscopy as well as by the chromatographic properties of the adduct on cellulose or poly(ethylenimine)- cellulose TLC and HPLC. The characteristics are identical to those of the adduct synthesized from benzenediazonium ion and guanine, identified by mass, UV/vis, and 1H-NMR spectroscopy as 8-(phenylazo)guanine. The results suggest strongly that benzenediazonium ion derived from Sudan I reacts with DNA in vitro to form the stable 8-(phenylazo)guanine adduct.

Nitrosation of 1-phenyl-3-(pyridylmethyl)ureas and the reactivity of two nitrosated isomers

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Reactions of Benzenediazonium Ions with Guanine and Its Derivatives

Guanine reacts with several benzenediazonium ions rapidly in aqueous solution at pH 10.5 to form 8-(arylazo)guanines in good yield.The reaction of guanine with 4-bromobenzenediazonium ion forms ε-guanine about 50-fold more rapidly than the reaction of adenine with this ion to yield 6-purine under these experimental conditions.Guanosine reacts much more slowly than guanine with the benzenediazonium ions in aqueous solution at pH 8.5 or 10.5 to give 8-arylguanosines.The structures of these products were established by their spectroscopic properties and by their quantitative conversion to 8-arylguanines. 5'-Guanylic acid also reacts quite slowly with the benzenediazonium ions in aqueous solution at pH 10.5.Only the compounds with strong electron-withdrawing groups yield N-2 triazenes at ambient temperature.No 8-aryl or 8-arylazo compounds are formed with 5'-guanylic acid at this temperature.However, 4-bromo- and 4-sulfobenzenediazonium ions react with 5'-guanylic acid at higher temperatures to yield the 8-aryl-5'-guanylic acids in low yield.The structures of these products were proven by hydrolysis to 8-arylguanines.The 8-arylguanosines and the 8-aryl-5'-guanylic acids are formed via free-radical phenylation reactions.The factors governing the reactivity of the adenines and the guanines are discussed.