171523-03-8

Basic information

• Product Name: Methanone, (4-methylphenyl)[5-(phenyl-1H-pyrrol-2-ylmethyl)-1H-pyrrol-2-yl]-
• CAS NO: 171523-03-8
• Molecular Formula: C23H20N2O
• Molecular Weight: 340.425
• Mol File: 171523-03-8.mol

Chemical Properties

• CAS DataBase Reference: Methanone, (4-methylphenyl)[5-(phenyl-1H-pyrrol-2-ylmethyl)-1H-pyrrol-2-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (4-methylphenyl)[5-(phenyl-1H-pyrrol-2-ylmethyl)-1H-pyrrol-2-yl]-(171523-03-8)
• EPA Substance Registry System: Methanone, (4-methylphenyl)[5-(phenyl-1H-pyrrol-2-ylmethyl)-1H-pyrrol-2-yl]-(171523-03-8)

Safety Data

• Hazardous Substances Data: 171523-03-8(Hazardous Substances Data)

Upstream product

• 816454-48-5 10-(9-borabicyclo[3.3.1]non-9-yl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 74032-45-4 S-2-pyridyl 4-methylbenzothiolate 
• 107798-98-1 5-phenyldipyrromethane 
• 874-60-2 4-methyl-benzoyl chloride 
• 750646-77-6 10-(9-borabicyclo[3.3.1]non-9-yl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 159152-12-2 5-(4-iodophenyl)dipyrromethane 

Downstream Products

• 171523-05-0 1-(p-methylbenzoyl)-5-phenyl-9-<2-(p-chlorophenyl)-1,3-benzoxathiolyl>dipyrromethane 
• 352423-80-4 {5-[phenyl-(1H-pyrrol-2-yl)-methyl]-1H-pyrrol-2-yl}-p-tolyl-methanol 
• 852244-78-1 1-(4-methylbenzoyl)-5-phenyl-9-bromodipyrromethane 
• 171523-04-9 1,9-bis-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 171523-00-5 1-(p-methylbenzoyl)-5-phenyl-9-(p-chlorobenzoyl)dipyrromethane 
• 171523-19-6 (4-Chloro-phenyl)-(5-{[5-(hydroxy-p-tolyl-methyl)-1H-pyrrol-2-yl]-phenyl-methyl}-1H-pyrrol-2-yl)-methanol 
• 750646-90-3 10-(dibutylboryl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 816454-44-1 dibutyl[5,10-dihydro-1,9-bis(4-methylbenzoyl)-5-phenyldipyrrinato]tin(IV) 
• 750646-77-6 10-(9-borabicyclo[3.3.1]non-9-yl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 750646-91-4 10-(dimethylboryl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane 
• 132313-39-4 5,15-bis-(4-methylphenyl)-10,20-diphenyl-porphyrin 

Relevant articles and documents

Metal complexation of 1-acyldipyrromethanes and porphyrins formed therefrom

A first aspect of the invention is a method of making a porphyrin-metal complex, comprising: (a) providing a first reagent selected from the group consisting of 1-acyldipyrromethanes, 1-acyldipyrrins, dipyrromethane-1-carbinols 1,9-diacyldipyrromethanes and 1,9-diacyldipyrrins; and then (b) condensing the first reagent with either itself (in the case of 1-acyldipyrromethanes, 1-acyldipyrrins, and dipyrromethane-1-carbinols) or a dipyrromethane (in the case of 1,9-diacyldipyrromethanes and 1,9-diacyldipyrrins) in a reaction mixture comprising a solvent and a second reagent selected from the group consisting of palladium and copper complexes to produce the porphyrin-metal complex (with the metal being palladium or copper). In preferred embodiments of the foregoing, the reaction mixture further comprises a base such as KOH or NaH.

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.

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.

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

Boron-complexation strategy for use with 1-acyldipyrromethanes

1-Acyldipyrromethanes are important precursors in rational syntheses of diverse porphyrinic compounds. 1-Acyldipyrromethanes are difficult to purify, typically streaking upon chromatography and giving amorphous powders upon attempted crystallization. A solution to this problem has been achieved by reacting the 1-acyldipyrromethane with a dialkylboron triflate (e.g., Bu 2B-OTf or 9-BBN-OTf) to give the corresponding B,B-dialkyl-B-(1- acyldipyrromethane)boron(III) complex. The reaction is selective for a 1-acyldipyrromethane in the presence of a dipyrromethane. The 1-acyldipyrromethane-boron complexes are stable to routine handling, are soluble in common organic solvents, are hydrophobic, crystallize readily, and chromatograph without streaking. The 1-acyldipyrromethane can be liberated in high yield from the boron complex upon treatment with 1-pentanol. Alternatively, the 1-acyldipyrromethane-boron complex can be used in the formation of a trans-A2B2-porphyrin. In summary, the boron-complexation strategy has broad scope and greatly facilitates the isolation of 1-acyldipyrromethanes.

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

A Tin-Complexation Strategy for Use with Diverse Acylation Methods in the Preparation of 1,9-Diacyldipyrromethanes

The acylation of dipyrromethanes to form 1,9-diacyldipyrromethanes is an essential step in the rational synthesis of porphyrins. Although several methods for acylation are available, purification is difficult because 1,9-diacyldipyrromethanes typically st

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.

Rational Syntheses of Porphyrins Bearing up to Four Different Meso Substituents

Porphyrins bearing specific patterns of substituents are crucial building blocks in biomimetic and materials chemistry. We have developed methodology that avoids statistical reactions, employs minimal chromatography, and affords up to gram quantities of regioisomerically pure porphyrins bearing predesignated patterns of up to four different meso substituents. The methodology is based upon the availability of multigram quantities of dipyrromethanes. A procedure for the diacylation of dipyrromethanes using EtMgBr and an acid chloride has been refined. A new procedure for the preparation of unsymmetrical diacyl dipyrromethanes has been developed that involves (1) monoacylation with EtMgBr and a pyridyl benzothioate followed by (2) introduction of the second acyl unit upon reaction with EtMgBr and an acid chloride. The scope of these acylation methods has been examined by preparing multigram quantities of diacyl dipyrromethanes bearing a variety of substituents. Reduction of the diacyl dipyrromethane to the corresponding dipyrromethane-dicarbinol is achieved with NaBH4 in methanolic THF. Porphyrin formation involves the acid-catalyzed condensation of a dipyrromethane-dicarbinol and a dipyrromethane followed by oxidation with DDQ. Optimal conditions for the condensation were identified after examining various reaction parameters (solvent, temperature, acid, concentration, time). The conditions identified (2.5 mM reactants in acetonitrile containing 30 mM TFA at room temperature for 3B, trans-A2B2, trans-AB2C, cis-A2B2, cis-A2BC, and ABCD were prepared, including >1-g quantities of three porphyrins.

Rational Synthesis of Trans-Substituted Porphyrin Building Blocks Containing One Sulfur or Oxygen Atom in Place of Nitrogen at a Designated Site

The use of heteroatom-substituted porphyrins in bioorganic and materials chemistry requires the ability to position a variety of substituents in a controlled manner about the porphyrin periphery. We describe a rational route to trans-AB2C-type