132313-39-4

Basic information

• Product Name: 5,15-bis-(4-methylphenyl)-10,20-diphenyl-porphyrin
• Synonyms: 5,15-bis-(4-methylphenyl)-10,20-diphenyl-porphyrin
• CAS NO: 132313-39-4
• Molecular Weight: 642.803
• Mol File: 132313-39-4.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 5,15-bis-(4-methylphenyl)-10,20-diphenyl-porphyrin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,15-bis-(4-methylphenyl)-10,20-diphenyl-porphyrin(132313-39-4)
• EPA Substance Registry System: 5,15-bis-(4-methylphenyl)-10,20-diphenyl-porphyrin(132313-39-4)

Safety Data

• Hazardous Substances Data: 132313-39-4(Hazardous Substances Data)

Upstream product

• 107798-98-1 5-phenyldipyrromethane 
• 250695-22-8 1,9-bis[α-hydroxy-α-(p-tolyl)methyl]-5-phenyldipyrromethane 
• 352423-80-4 {5-[phenyl-(1H-pyrrol-2-yl)-methyl]-1H-pyrrol-2-yl}-p-tolyl-methanol 
• 5720-05-8 4-methylphenylboronic acid 
• 1057140-05-2 5,15-dibromo-10,20-diphenylporphyrin 
• 104-87-0 4-methyl-benzaldehyde 
• 100-52-7 benzaldehyde 
• 147804-55-5 5-(4-methylphenyl)dipyrromethane 
• 750646-77-6 10-(9-borabicyclo[3.3.1]non-9-yl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 750646-90-3 10-(dibutylboryl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 82297-89-0 (4-fluoro-3-methyl)phenylmagnesium bromide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 98-88-4 benzoyl chloride 
• 132313-37-2 5-(4-Fluoro-3-methylphenyl)-1-(4-methoxybenzoyl)dipyrromethane 

Relevant articles and documents

Effects of aldehyde or dipyrromethane substituents on the reaction course leading to meso-substituted porphyrins

To better understand the effects of diverse substituents on reactions leading to porphyrins, pyrrole+aldehyde condensations and related reactions of dipyrromethanes were examined. The course of pyrrole+aldehyde condensations was investigated by monitoring the yield of porphyrin (by UV-Vis spectroscopy), reaction of aldehyde (by TLC), and changes in the composition of oligomers (by laser desorption mass spectrometry). Reaction reversibility was examined via exchange experiments. Reversibility of reactions leading to porphyrin was further probed with studies of dipyrromethanes. The reaction course was found to depend on the nature of the substituent and the acid catalyst. Alkyl or electron-donating substituents displayed levels of reversibility (exchange/scrambling) on par or greater than that of the phenyl substituent, whereas electron-withdrawing or sterically bulky substituents exhibited little to no reversibility. The results obtained provide insight into the electronic and steric effects of different substituents and should facilitate the design of synthetic plans for preparing porphyrinic macrocycles. Graphical abstract.

Synthesis of meso-tetraphenyl porphyrins via condensation of dipyrromethanes with N-tosyl imines

A new synthetic route for the synthesis of 5,10,15,20-tetraphenyl porphyrins has been developed based on the reaction of 5-substituted dipyrromethanes with N-tosyl imines in the presence of a metal triflate catalyst. meso-Substituted tetraphenyl porphyrins were synthesized in a two-step process. The first step of the method is the metal triflate-catalyzed condensation of 5-substituted dipyrromethanes with N-tosyl imines to form a porphyrinogen intermediate and the second step is the oxidation of the porphyrinogen to porphyrin. The method was applied to the synthesis of trans-A2B2-tetraarylporphyrins and the products were obtained with only a trace amount of one scrambling product. The synthesis of two important building blocks for porphyrin synthesis, mono and di-sulfonamide alkylated 5-substituted dipyrromethanes, was achieved by the addition of 5-substituted dipyrromethane to N-tosyl imine. The application of mono and di-sulfonamide alkylated 5-substituted dipyrromethanes in '2+2' porphyrin formation reactions is presented.

Boron complexation strategy for use in manipulating 1-acyldipyrromethanes

A method of making a metal complex comprises combining a 1-monoacyldipyrromethane with a compound of the formula R1R2MX, wherein M is boron, R1 and R2 are each independently organic substituents; and X is an anion leaving group; to produce a metal complex of the formula DMR1R2 wherein DH is a 1-monoacyldipyrromethane. The methods and complexes are useful for the purification and synthesis of dipyrromethanes and porphyrins.