262267-31-2

Upstream product

• 2637-34-5 2-Sulfanylpyridine 
• 2251-50-5 pentafluorobenzoylchloride 

Downstream Products

• 1046493-87-1 5-(4-methylphenyl)-1-(pentafluorobenzoyl)dipyrromethane 
• 1051917-91-9 5-(4-tert-butylphenyl)-1-(pentafluorobenzoyl)dipyrromethane 
• 1595241-54-5 1-(pentafluorobenzoyl)-2,3-diphenyl-5-(pentafluorophenyl)dipyrromethane 
• 1595241-57-8 9-(pentafluorobenzoyl)-2,3-diphenyl-5-(pentafluorophenyl)dipyrromethane 
• 1595241-50-1 2-(pentafluorobenzoyl)-3,4-diphenylpyrrole 
• 1402557-16-7 3-[pentafluorophenyl-(5-pentafluorobenzoyl-1H-pyrrol-2-yl)methane]-1-triisopropylsilylindole 
• 1379604-91-7 C₃₃H₁₂F₁₅N₃O 
• 1379604-99-5 C₄₄H₁₆F₂₀N₄O 
• 1379605-00-1 C₅₁H₁₅F₂₅N₄O₂ 
• 1327160-37-1 5,10,15-tris(pentafluorophenyl)-7,13-diaza-22,23-dicarbabilane 
• 1379604-96-2 C₂₉H₁₁F₁₅N₂O₂ 
• 1327160-36-0 5,10,15-tris(pentafluorophenyl)-1,8-diaza-21,22-dicarbabilane 

Relevant academic research and scientific papers

Facile synthesis of 1,9-diacyldipyrromethanes

The present invention provides a method of making a metal complex. The method comprises the steps of: (a) acylating a dipyrromethane or a 1-monoacyldipyrromethane to form a mixed reaction product comprising a 1,9-diacyidipyrromethane; (b) combining the re

9-Acylation of 1-acyldipyrromethanes containing a dialkylboron mask for the α-acylpyrrole motif

1,9-Diacyldipyrromethanes are important precursors to porphyrins, yet synthetic access remains limited owing to (1) poor conversion in the 9-acylation of 1-acyldipyrromethanes and (2) handling difficulties because acyldipyrromethanes typically streak upon

Rational Synthesis of Meso-Substituted Chlorin Building Blocks

Chlorins provide the basis for plant photosynthesis, but synthetic model systems have generally employed porphyrins as surrogates due to the unavailability of suitable chlorin building blocks. We have adapted a route pioneered by Battersby to gain access to chlorins that bear two meso substituents, a geminal dimethyl group to lock in the chlorin hydrogenation level, and no flanking meso and β substituents. The synthesis involves convergent joining of an Eastern half and a Western half. A 3,3-dimethyl-2,3-dihydrodipyrrin (Western half) was synthesized in four steps from pyrrole-2-carboxaldehyde. A bromodipyrromethane carbinol (Eastern half) was prepared by sequential acylation and bromination of a 5-substituted dipyrromethane followed by reduction. Chlorin formation is achieved by a two-flask process of acid-catalyzed condensation followed by metal-mediated oxidative cyclization. The latter reaction has heretofore been performed with copper templates. Investigation of conditions for this multistep process led to copper-free conditions (zinc acetate, AgIO3, and piperidine in toluene at 80 °C for 2 h). The zinc chlorin was obtained in yields of ～10% and could be easily demetalated to give the corresponding free base chlorin. The synthetic process is compatible with a range of meso substituents (p-tolyl, mesityl, pentafluorophenyl, 4-[2-(trimethylsilyl)ethynyl]phenyl, 4-iodophenyl). Altogether four free base and four zinc chlorins have been prepared. The chlorins exhibit typical absorption spectra, fluorescence spectra, and fluorescence quantum yields. The ease of synthetic access, presence of appropriate substituents, and characteristic spectral features make these types of chlorins well suited for incorporation in synthetic model systems.

Efficient synthesis of monoacyl dipyrromethanes and their use in the preparation of sterically unhindered trans-porphyrins

The condensation of an aldehyde with a dipyrromethane bearing a sterically unhindered aryl substituent at the 5-position typically results in low yield and a mixture of porphyrin products derived from acidolytic scrambling. We have developed a concise nonscrambling synthesis of such trans-porphyrins that takes advantage of the availability of multigram quantities of dipyrromethanes. This route involves the selective monoacylation of the dipyrromethanes with a pyridyl thioester, reduction of the monoacyl dipyrromethane to the corresponding carbinol, and self- condensation of the carbinol to form the porphyrin. The monoacylation procedure has wide scope as demonstrated by the preparation of a set of 15 diverse monoacyl dipyrromethanes in good yield at the multigram scale. The dipyrromethanecarbinol self-condensation reaction is extremely rapid (3 min) under mild room-temperature conditions and affords the trans-porphyrin in 16- 28% yield. Analysis by laser-desorption mass spectrometry (LD-MS) of samples from the crude reaction mixture revealed no scrambling within the limit of detection (1 part in 100). The self-condensation is compatible with a range of electron-withdrawing or -releasing substituents as well as substituents for building block applications (TMS-ethyne, ethyne, iodo, ester). The absence of any detectable scrambling in the self-condensation enables a simple purification. The synthesis readily affords gram quantities of pure, sterically unhindered trans-porphyrins in a process involving minimal chromatography.