26933-87-9

Basic information

• Product Name: 2-Pyrenecarboxaldehyde
• Synonyms: 2-PYRENECARBALDEHYDE
• CAS NO: 26933-87-9
• Molecular Formula: C₁₇H₁₀O
• Molecular Weight: 230.26
• Mol File: 26933-87-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Pyrenecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrenecarboxaldehyde(26933-87-9)
• EPA Substance Registry System: 2-Pyrenecarboxaldehyde(26933-87-9)

Safety Data

• Hazardous Substances Data: 26933-87-9(Hazardous Substances Data)

Upstream product

• 1714-27-8 2-Bromopyrene 
• 68-12-2 N,N-dimethyl-formamide 
• 781-17-9 4,5,9,10-tetrahydropyrene 
• 68841-74-7 2-carbethoxypyrene 
• 24471-48-5 2-hydroxymethylpyrene 

Downstream Products

• 1618084-24-4 C₃₄H₂₀Br₂O 
• 1252600-26-2 1-(4'-hydroxyphenyl)-4-pyren-2-yl-2,3-diaza-1,3-butadiene 
• 801220-52-0 2′-amino-2′-deoxy-2′-N-methyl-2′-N-(pyren-1-ylmethyl)-5′-O-(4,4′-dimethoxytrityl)uridine 
• 801220-49-5 2′-amino-2′-deoxy-2′-N-(pyren-1-ylmethyl)-5′-O-(4,4′-dimethoxytrityl)uridine 
• 24471-48-5 2-hydroxymethylpyrene 
• 97325-55-8 1,3-di(2-pyrenyl)propane 

Relevant articles and documents

Nickel(II)-Catalyzed Selective (E)-Olefination of Methyl Heteroarenes Using Benzyl Alcohols via Acceptorless Dehydrogenative Coupling Reaction

An efficient catalytic protocol for the synthesis of selective (E)-olefins by the newly synthesized nickel complexes via greener acceptorless dehydrogenative coupling methodology is presented. Two nickel(II) N, S chelating complexes were structurally characterized with the aid of spectral and single crystal X-ray diffraction methods. Olefination of 2-methylheteroarenes with benzyl alcohols via acceptorless dehydrogenative coupling is achieved by inexpensive nickel(II) catalysts. The present olefination protocol is simple and furnishes the desired 2-alkenylheteroarenes in 35 h and yields in the range of 40–93 %. The dehydrogenative coupling reaction proceeds via the generation of an aldehyde intermediate and produces water and hydrogen as sole by-products. The wide substrate scope of this catalytic reaction covered the synthesis of drug intermediates.

Efficient oxidation of promutagenic hydroxymethylpyrenes by cDNA-expressed human alcohol dehydrogenase ADH2 and its inhibition by various agents

Alkylated polycyclic aromatic hydrocarbons can be metabolically activated via benzylic hydroxylation and sulphation to electrophilically reactive esters. However, we previously found that the predominant biotransformation route for the hepatocarcinogen 1-hydroxymethylpyrene (1-HMP) in the rat in vivo is the oxidation of the side chain by alcohol dehydrogenases (ADHs) and aldehyde dehydrogenases to the carboxylic acid. Inhibition of this pathway by ethanol (competing ADH substrate) or 4-methylpyrazole (ADH inhibitor) led to a dramatic increase in the 1-HMP-induced DNA adduct formation in rat tissues in the preceding study. In order to elucidate the role of individual ADHs in the metabolism of alkylated polycyclic aromatic hydrocarbons, we expressed the various members of the human ADH family in bacteria. Cytosolic preparations from bacteria expressing ADH2 clearly oxidized hydroxymethylpyrene isomers (1-, 2- and 4-HMP) with the highest rate. This form was purified to near homogeneity to perform detailed kinetic analyses. High catalytic efficiencies (Vmax/Km) were observed with HMPs. Thus, this value was 10,000-fold higher for 2-HMP than for the reference substrate, ethanol. The corresponding aldehydes were also efficiently reduced by ADH2. 4-Methylpyrazole inhibited the oxidation of the HMP isomers as well as the reverse reaction. Daidzein, cimetidine and the competing substrate ethanol were further compounds that inhibited the ADH2-mediated oxidative detoxification of 1-HMP.