2869-59-2

Basic information

• Product Name: Dibenzo[def,p]chrysene-10-carbaldehyde
• Synonyms: Dibenzo[def,p]chrysene-10-carbaldehyde
• CAS NO: 2869-59-2
• Molecular Formula: C25H14 O
• Molecular Weight: 330.39
• Mol File: 2869-59-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 427.82°C (rough estimate)
• Flash Point: 419.9°C
• Appearance: /
• Density: 1.0905 (rough estimate)
• Vapor Pressure: 1.12E-14mmHg at 25°C
• Refractive Index: 1.6380 (estimate)
• CAS DataBase Reference: Dibenzo[def,p]chrysene-10-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzo[def,p]chrysene-10-carbaldehyde(2869-59-2)
• EPA Substance Registry System: Dibenzo[def,p]chrysene-10-carbaldehyde(2869-59-2)

Safety Data

• Hazardous Substances Data: 2869-59-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C25H14O/c26-14-18-7-3-6-16-13-17-12-11-15-5-4-10-20-19-8-1-2-9-21(19)25(22(16)18)24(17)23(15)20/h1-14H

Upstream product

• 191-30-0 Dibenzo[a,l]pyrene 
• 93-61-8 N-methyl-N-phenylformamide 

Relevant articles and documents

Efficient syntheses of C8-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA

(Chemical Equation Presented) The synthesis of the C8-aryl adducts of adenine and guanine formed by reaction of the radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BP) and dibenzo[def,p]chrysene (DBC), with DNA is reported. The synthetic approach involves in the key step direct reaction of a PAH aldehyde with a di- or triamine precursor of a purine. The method is operationally simple, affords good yields of adducts, and is broad in its scope. The C 8-aryl adducts of adenine and guanine derived from BP (6-BP-8-Ade and 6-BP-8-Gua) and DBC (10-DBC-8-Ade and 10-DBC-8-Gua) were synthesized in good yields by this method. Analogous C8-aryl adenine and guanine derivatives of other PAHs (anthracene, benz[a]anthracene, and chrysene) were also readily prepared via this approach. This method of synthesis is superior to the only method mat is currently available. It entails direct reaction of short-lived PAH radical cations (generated electrochemically or chemically) with 2′-deoxyribonucleosides or the corresponding purine bases. It provides the adducts in low yields accompanied by complex mixtures of secondary products. An alternative synthesis that involves Pd-catalyzed Suzuki-Miyaura coupling of arylboronic acids with 8-bromopurine nucleosides was also investigated. Although the C8-purine adducts of PAHs, such as naphthalene, phenanthrene, pyrene, and chrysene, could be prepared by this method, analogous adducts of carcinogenic PAHs and other structurally related PAHs, e.g., anthracene, benz[a]anthracene, benzo[a]pyrene, and dibenzo[def,p]chrysene, could not be obtained. This difference was shown to be a consequence of the facility of competing hydrolytic deboronation of the corresponding arylboronic acids.