10512-70-6

Basic information

• Product Name: 5-bromo-4-nitro-1-(2,3,5-tri-O-acetylpentofuranosyl)-1H-imidazole
• Synonyms: 1H-Imidazole, 5-bromo-4-nitro-1-(2,3,5-tri-O-acetylpentofuranosyl)-
• CAS NO: 10512-70-6
• Molecular Formula: C₁₄H₁₆BrN₃O₉
• Molecular Weight: 450.1955
• Mol File: 10512-70-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 565.2°C at 760 mmHg
• Flash Point: 295.6°C
• Density: 1.8g/cm³
• Vapor Pressure: 8.5E-13mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: 5-bromo-4-nitro-1-(2,3,5-tri-O-acetylpentofuranosyl)-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-4-nitro-1-(2,3,5-tri-O-acetylpentofuranosyl)-1H-imidazole(10512-70-6)
• EPA Substance Registry System: 5-bromo-4-nitro-1-(2,3,5-tri-O-acetylpentofuranosyl)-1H-imidazole(10512-70-6)

Safety Data

• Hazardous Substances Data: 10512-70-6(Hazardous Substances Data)

Upstream product

• 6963-65-1 5-bromo-4-nitro-1H-imidazole 
• 13035-61-5 1,2,3,5-tetraacetylribose 

Downstream Products

• 10357-25-2 5-Bromo-4-nitro-1-β-D-ribofuranosylimidazole 
• 132665-81-7 5-Bromo-4-nitro-1-(5-deoxy-5-iodo-β-D-ribofuranosyl)imidazole 

Relevant articles and documents

A novel nitroimidazole compound formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-guanosine

Peroxynitrite reacts with 2′,3′,5′-tri-O-acetyl-guanosine to yield a novel compound identified as 1-(2,3,5-tri-O-acetyl-β-D-erythro-pentofuranosyl) -5-guanidino-4-nitroimidazole (6). This characterization was achieved using a combination of UV/vis spectroscopy and ESI-MS. Additionally, 1 -(β-D-erythro-pentofuranosyl) 5-guanidino-4-nitroimidazole (6a) was synthesized by an independent route, characterized by UV/vis spectroscopy, ESI-MS, and 1H- and 13C NMR, and shown to be identical to deacetylated 6. This product is extremely stable in aqueous solution at both pH extremes and is formed in significant yields. These characteristics suggest that this lesion may be useful as a specific biomarker of peroxynitrite-induced DNA damage. We also observed formation of 2′,3′,5′-tri-O-acetyl-8-nitroguanosine (2′,3′,5′-tri-O-acetyl-8-NO2Guo), 2-amino-5-[(2,3,5 tri-O-acetyl-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one (2′,3′,5′-tri-O-acetyl-Iz), and the peroxy-nitrite-induced oxidation products of 2′,3′,5′-tri-O-acetyl-8-oxoGuo. The formation of 6 and 2′,3′,5′-tri-O-acetyl-8-NO2Guo was rationalized by a mechanism invoking formation of the guanine radical.

Purine nucleosides. XX. The synthesis of 7-beta-D-ribofuranosylpurines from imidazole nucleoside derivatives.

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