248606-49-7

Upstream product

• 109-97-7 pyrrole 
• 123-11-5 4-methoxy-benzaldehyde 
• 22112-78-3 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin 
• 14674-38-5 N-(4-methoxybenzylidene)-p-toluenesulfonamide 
• 176446-62-1 5-(4-methoxyphenyl)dipyrromethane 

Downstream Products

• 22112-78-3 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin 
• 27226-57-9 5,10,15,20-tetrakis(p-methoxyphenyl)chlorin 

Relevant academic research and scientific papers

Synthesis of meso-substituted corroles and porphyrins using iodine as a catalyst

Abstract: Different types of corroles and porphyrins are synthesized from substituted aldehydes and pyrrole. The current synthetic method involves iodine as catalyst and proceeds at room temperature itself. By varying the amounts of reactants (i.e., pyrrole and aldehydes), the corrole and porphyrins were obtained in good to excellent yields. These products were characterized by 1H-NMR, UV-visible, and HRMS techniques. The reaction approach utilizes the readily available pyrrole and substituted aldehydes as starting materials and makes this reaction highly attractive in diversity-oriented synthesis. Graphic abstract: Different types of porphyrins and corroles are synthesized from substituted aldehydes and pyrrole using iodine as a catalyst and the reaction proceeds at room temperature itself. By varying the amount of reactants (i.e. pyrrole and aldehydes), the porphyrins and corroles are obtained in good to excellent yields.[Figure not available: see fulltext.]

Porphyrin synthesis using mechanochemistry: Sustainability assessment

Looking for sustainable synthetic methodologies, mechanochemistry as a new tool for one-step and two-step approaches for the synthesis of meso-substituted porphyrins was explored. The best results were obtained in a two-step procedure, under liquid-assisted grinding in the oxidation step using 2-methyltetrahydrofuran, an environmentally acceptable solvent, and MnO2 as a heterogeneous oxidant. The sustainability was assessed using two sustainability metrics, E-factor and EcoScale, which allow comparison between procedures and methods.

Synthesis and characterization of tetraarylporphyrins in the presence of nano-TiCl4·SiO2

[MediaObject not available: see fulltext.] Synthesis of tetraarylporphyrins by the coupling of an aromatic aldehyde and pyrrole using nano-TiCl4·SiO2 as mild, inexpensive, and highly efficient catalyst is studied in the present article.

Cellulose sulfuric acid as a biodegradable and recoverable solid acid catalyst for one pot synthesis of substituted pyrroles under solvent-free conditions at room temperature

A new and efficient method for the preparation of N-substituted pyrroles from one-pot condensation reaction of 2,5-hexandione with amines and diamines in the presence of cellulose sulfuric acid (CSA) as a bio-supported catalyst at room temperature under solvent-free conditions is presented. This new protocol has the advantages of easy availability, stability, reusability and eco-friendly of the catalyst, high to excellent yields, simple experimental and work-up procedure.

Effects of methoxy-substituted metalloporphyrins in catalytic alkene epoxidation by n-Bu 4NHSO 5

TPPMnOAc and four different kinds of manganese tetraphenylporphyrin acetates were synthesized using different numbers of methoxy substituents in various positions of the phenyl rings. These porphyrins were used as catalysts in the epoxidation of various alkenes with tetra-n-butylammonium hydrogen monopersulfate (n-Bu 4NHSO 5) as the oxidant and imidazole as the axial base. The following order of catalytic activity was obtained: TPPMnOAc ≥ T(2,3-OMeP) PMnOAc > T(4-OMeP) PMnOAc > T(3,4-OMeP) PMnOAc > T(2,4,6-OMeP) PMnOAc. By studying the UV-vis spectra in the reaction solution, the stability of the applied methoxy porphyrins and the effect of this factor on obtained yields were investigated. Lower catalytic activity in some of the methoxy porphyrins emphasized steric effects and special hydrogen bonding among the reaction elements. However, the stability of T(2,3-OMeP) PMnOAc under our reaction condition was considerable and high activity was observed. By adding small amounts of alcohol to the reaction solution, the effect of the solvent mixture was previewed and steps were taken to identify the active intermediate of the catalyst in these conditions. Copyright

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.

Efficient synthesis of meso-tetraarylporphyrins using i2 as catalyst and ibx as oxidant

meso-Tetraarylporphyrins are synthesized from pyrrole and substituted benzaldehydes by a catalytic amount of I2 as catalyst and o-iodoxybenzoic acid (IBX) as oxidant in two steps and one flask. The advantages of this method include the use of inexpensive and easily available catalyst, avoidance of heavy consumption of CH2Cl2, innocuous oxidant, and good yields.

Novel synthesis of meso-tetraarylporphyrins by using I2 as catalyst and air as oxidant under thermal or UV conditions

An efficient and novel synthesis of meso-tetraarylporphyrins is accomplished through iodine-catalyzed condensation of pyrrole, and aryl aldehydes and subsequent oxidation by air under thermal or ultraviolet (UV) irradiation conditions. The advantages of this procedure include good yields and a green nature. Copyright

Novel synthesis of meso-tetraarylporphyrins using CF3SO 2Cl under aerobic oxidation

meso-Tetraarylporphyrins are synthesized from pyrrole and aryl aldehydes cleanly and efficiently in one pot at room temperature using equimolar amount of CF3SO2Cl in the presence of air as oxidant. By this novel method 5,10,15,20-tetraarylporphyrins can be prepared in excellent yields.

Investigations into the mechanism of action of nitrobenzene as a mild dehydrogenating agent under acid-catalysed conditions

Protonated nitrobenzene can be used to dehydrogenate a range of hydrocarbons, which already possess at least one double bond. Kinetic and spectroscopic results, together with known electrode potentials, yield approximate limits within which protonated nitrobenzenes can be expected to effect dehydrogenation of hydroaromatic compounds. A high yielding synthesis of benzo[j]fluoranthene is described.