248606-50-0

Basic information

• Product Name: 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinogen
• Synonyms: 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinogen
• CAS NO: 248606-50-0
• Molecular Weight: 758.577
• Mol File: 248606-50-0.mol

Chemical Properties

• CAS DataBase Reference: 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinogen(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinogen(248606-50-0)
• EPA Substance Registry System: 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinogen(248606-50-0)

Safety Data

• Hazardous Substances Data: 248606-50-0(Hazardous Substances Data)

Upstream product

• 3157-65-1 N-(p-chlorobenzylidene)-p-toluenesulfonamide 
• 137018-26-9 2,2'-((4-chlorophenyl)methylene)bis(1H-pyrrole) 
• 109-97-7 pyrrole 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 22112-77-2 5,10,15,20-tetra-(4-chlorophenyl)porphyrin 

Relevant articles and documents

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.

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.]

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.

Controlled porphyrinogen oxidation for the selective synthesis of meso-tetraarylchlorins

Chlorins have been synthesized through the reduction of the corresponding porphyrins although theoretically they can be obtained from reduced macrocycle forms as porphyrinogens. A new method for the oxidation of meso- tetraarylporphyrinogens was developed generating a substantial amount of chlorin relatively to porphyrin. The structure of the porphyrinogen, particularly the presence of substituents on the meso-phenyl groups, is decisive for the final yield of chlorin. In the case of meso-tetrakis(2,6-dichlorophenyl)porphyrinogen, 92% of the corresponding chlorin is obtained.

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.

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.

Phosphorus pentachloride (PCl5) mediated synthesis of tetraarylporphyrins

A new synthesis of porphyrins from pyrrole and substituted benzaldehydes is described, with PCl5 as catalyst. Aromatic aldehydes condense irreversibly with pyrrole in the presence of this catalyst, and aerobic oxidation of porphyrinogen provides functionalized porphyrins in yields of 20-65%.

Synthesis of meso-tetraarylporphyrins in air with silica chloride as catalyst

Meso-tetraarylporphyrins (14 examples) are prepared efficiently by condensation of pyrrole with aromatic aldehydes in the presence of silica chloride, followed by air oxidation. The method is compared with other published procedures.

Improved syntheses of 5,10,15,20-tetrakisaryl- and tetrakisalkylporphyrins

Three significant modifications to existing methods for the preparation of the important 5,10,15,20-tetrakisarylporphyrins have improved isolated yields, simplified work-up and made large-scale synthesis feasible. Two tetrakisalkylporphyrins were also produced. A two-stage approach using hydrogen peroxide in acetic acid as second stage oxidant gave good yields but for ease of isolation and convenience in working on a large scale, the one-pot approach is preferred. No one method appears to be suitable for all such tetrakisarylporphyrins and, for best yields, the method of preparation needs to be chosen carefully. Application of statistical optimisation techniques (factorial two design and simplex operation) led to considerably enhanced yields for the one-pot method. For one of the two-stage modifications, significant amounts of chlorins were observed, sometimes of such magnitude as to make it suitable as a method for their preparation.