20998-75-8

Basic information

• Product Name: TPP
• Synonyms: RARECHEM AS SA 0001;TETRAPHENYLPORFYRIN;TETRAPHENYLPORPHINE;TETRAPHENYLPORPHINE METAL FREE;TETRAPHENYLPORPHYRIN;MESO-TETRAPHENYLPORPHYRIN;MESO-TETRAPHENYLPROPHYRIN;MESO-TETRAPHENYLPORPHINE
• CAS NO: 20998-75-8
• Molecular Formula: C44H30N4
• Molecular Weight: 614.74
• EINECS: 213-025-9
• Product Categories: Intermediates
• Mol File: 20998-75-8.mol

Chemical Properties

• Melting Point: 300 °C
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Dichloromethane (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: TPP(CAS DataBase Reference)
• NIST Chemistry Reference: TPP(20998-75-8)
• EPA Substance Registry System: TPP(20998-75-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 20998-75-8(Hazardous Substances Data)

Usage

Uses

Used in Photodynamic Therapy:
Tetraphenylporphyrin is used as a photosensitizer for photodynamic therapy (PDT), a medical treatment that involves the use of light, a photosensitizing agent, and oxygen to generate a reaction that kills target cells, such as cancer cells. Its ability to absorb light and generate reactive oxygen species makes it an effective agent in this application.
Used in Hydrogen Production:
Cobalt meso-tetraphenylporphrine is used as a hydrogen catalyst, playing a crucial role in facilitating the production of hydrogen, a clean and renewable energy source. The catalytic properties of this compound contribute to its importance in the field of energy production and storage.
Used in Cancer Research:
Meso-tetraphenylporphrine compounds are used as inhibitors of microtubule assembly in human cervix carcinoma cells. By disrupting the normal assembly of microtubules, these compounds can inhibit cell division and proliferation, making them valuable tools in the study and treatment of cancer.
Used in Coordination Chemistry:
Tetraphenylporphyrin is used as a building block for creating coordination complexes with metals such as cobalt and rhodium. These complexes exhibit unique properties and are of interest in various fields, including catalysis, materials science, and medicinal chemistry.
Used in Analytical Chemistry:
Due to its strong absorption in the visible region of the electromagnetic spectrum, Tetraphenylporphyrin is used as a colorimetric reagent for the detection and quantification of various metal ions and other analytes. Its sensitivity and selectivity make it a valuable tool in analytical chemistry.
Used in Materials Science:
The unique optical and electronic properties of Tetraphenylporphyrin make it a promising candidate for the development of advanced materials, such as organic semiconductors, light-harvesting systems, and molecular electronic devices.

InChI:InChI=1/C44H30N4/c1-5-13-29(14-6-1)41-33-21-23-35(45-33)42(30-15-7-2-8-16-30)37-25-27-39(47-37)44(32-19-11-4-12-20-32)40-28-26-38(48-40)43(31-17-9-3-10-18-31)36-24-22-34(41)46-36/h1-28,45,48H/b41-33-,41-34-,42-35+,42-37?,43-36-,43-38?,44-39-,44-40-

Upstream product

• 109-97-7 pyrrole 
• 100-52-7 benzaldehyde 
• 99-61-6 3-nitro-benzaldehyde 
• 122-85-0 para-acetamidobenzaldehyde 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 3011-34-5 4-hydroxy-3-nitrobenzaldehyde 
• 130413-37-5 4-(2-(2-chloroethoxy)ethoxy)benzaldehyde 
• 127572-74-1 4(e)-(2,5-Dihydroxyphenyl)cyclohexan-(e)-carbaldehyd 
• 82873-87-8 3-(propionyloxymethyl)benzaldehyde 
• 27226-54-6 tetraphenylporphyrinogen 
• 75400-63-4 2-(α-hydroxy-α-phenyl)methyl pyrrole 
• 79109-30-1 Pyridin-3-yl-(1H-pyrrol-2-yl)-methanol 
• 79109-29-8 (4-Nitro-phenyl)-(1H-pyrrol-2-yl)-methanol 
• 74133-06-5 sec-butyl zinc chloride 

Downstream Products

• 90731-31-0 (5Z,10Z,14Z,19Z)-5,10,15,20-Tetraphenyl-porphyrin; compound with 4-nitro-phenol 
• 131111-60-9 C₄₇H₃₅N₅ 
• 103522-59-4 5-[1-{5-[1-{5-[(5-Benzoyl-1H-pyrrol-2-yl)-methoxy-phenyl-methyl]-1H-pyrrol-2-yl}-1-phenyl-meth-(Z)-ylidene]-5H-pyrrol-2-yl}-1-phenyl-meth-(Z)-ylidene]-1,5-dihydro-pyrrol-2-one 
• 130471-40-8 5-[1-{5-[1-{5-[(5-Benzoyl-1H-pyrrol-2-yl)-ethoxy-phenyl-methyl]-1H-pyrrol-2-yl}-1-phenyl-meth-(Z)-ylidene]-5H-pyrrol-2-yl}-1-phenyl-meth-(Z)-ylidene]-1,5-dihydro-pyrrol-2-one 
• 142230-18-0 3-[4-((5Z,10Z,14Z,19Z)-10,15,20-Triphenyl-porphyrin-5-yl)-phenyl]-adamantane-1-carboxylic acid 
• 142230-17-9 C-{3-[4-((5Z,10Z,14Z,19Z)-10,15,20-Triphenyl-porphyrin-5-yl)-phenyl]-adamantan-1-yl}-methylamine 
• 103522-58-3 (4Z,9Z)-1,15,21,24-tetrahydro-19-benzoyl-15-hydroxy-5,10,15-triphenyl-23H-bilin-1-one 
• 36951-71-0 tris(4-sulfonatophenyl)monophenylporphyrin 
• 67605-65-6 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin 
• 116430-09-2 5,10,15-tris(4-nitrophenyl)-20-phenylporphyrin 

Relevant articles and documents

Physical basis of self-assembly. Part 2. A theoretical and experimental study of the self-assembly of a zinc meso-pyridyl porphyrin

A previously reported theoretical treatment for self-assembly macrocyclisations occurring under thermodynamic control has been tested experimentally. The fundamental quantities on which the treatment is based are the effective molarity (EM) of the self-assembling cyclic n-mer and the equilibrium constant for the intermolecular model reaction between monofunctional reactants (Kinter). Provided that estimates of EM and Kinter are available, this treatment can be used to predict not only whether the self-assembly process is more or less favoured, but also the distribution of all the species present in solution. Since Kinter values are approximately known from the literature, we have proposed a method, based on molecular modelling techniques, to estimate the EM. The method has been applied to the self-assembly of Zn(PyP3P), where PyP3P is 5-(4-pyridyl)-10,15,20-triphenylporphyrinato dianion. An EM greater than 0.1 mol L-1 has been estimated for its cyclotetramerisation by PM3 calculations, suggesting that self-assembly should be favoured in solvents like toluene and chloroform. Self-assembly of Zn(PyP3P) has been studied in these solvents by UV/visible spectroscopy. The data are consistent with the formation of the cyclotetramer, and at variance with the model of linear polymerisation. The experimental values of the EM were little affected by the nature of the solvent (EM values were 20 mol L-1 in toluene and 15 mol L-1 in chloroform), indicating that the solvent affects the process of self-assembly mainly through the value of Kinter.

Unusual properties of tetraphenylporphyrin copper complex

5,10,15,20-Tetraphenylporphyrin reacted with copper powder in boiling xylene on exposure to air (but not in an inert atmosphere) to give bright red copper complex which differed in properties from the initial porphyrin and its complexes with other metals.

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.]

EFFICIENT PERIPHERAL FUNCTIONALIZATION OF PORPHYRINS

Details are given for the mild and efficient synthesis of β-substituted "capped"-porphyrins and meso-tetraphenylporphyrins from the corresponding porphyrins.The nitro derivatives are cleanly reduced to β-aminoporphyrins, which are susceptible to hydrolysis but otherwise may be further derivatized on nitrogen by standard procedures.Treatment of β-nitroporphyrins with thiolate ions in DMF gave β-alkylthioporphyrins, β-arylthioporphyrins or the corresponding denitrated porphyrin, depending on the tiol.

Porphyrin architectures bearing functionalized xanthene spacers

A modular synthetic strategy for the construction of cofacial porphyrin architectures bearing hydrogen-bond synthons on a xanthene platform is presented. The convergent approach is based on a xanthene aldehyde-ester building block that is easily obtainable on a multigram scale with minimal purification. Treatment of this xanthene derivative with a variety of aryl aldehydes and pyrrole under standard Lindsey conditions affords a family of meso-substituted porphyrins bearing a single functionalized xanthene spacer. Direct modification of the hydrogen-bond synthon after macrocyclization proceeds smoothly to furnish porphyrin systems with a variety of cofacial functionalities (e.g., carboxylic acid, ester, amide). Porphyrins bearing two trans-functionalized xanthene spacers are prepared by the MacDonald [2 + 2] condensation of the xanthene aldehyde-ester with readily available 5-aryl-substituted dipyrromethanes such as 5-mesityldipyrromethane to afford the pure α,α- and α,β-porphyrin atropisomers after chromatographic separation. The versatility of this synthetic method offers intriguing opportunities for the use of these and related templates for the study of proton-coupled activation of small molecules.

Control of Porphyrin Planarity and Aggregation by Covalent Capping: Bissilyloxy Porphyrin Silanes

Porphyrins are cornerstone functional materials that are useful in a wide variety of settings, ranging from molecular electronics to biology and medicine. Their applications are often hindered, however, by poor solubilities that result from their extended

Investigation of a Synthesis of meso-Porphyrins Employing High Concentration Conditions and an Electron Transport Chain for Aerobic Oxidation

The room-temperature synthesis of meso-porphyrins has been investigated at aldehyde and pyrrole concentrations >/= 0.1 M using tetraphenylporphyrin (TPP) and tetramesitylporphyrin (TMP) as models.The decline in yield that occurs at higher reactant concent

Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole

Use of pivalaldehyde in mixed acid-catalyzed condensations of an aryl aldehyde with pyrrole allows the isolation and structural characterization of stable porphomethenes (5,10,15,22-tetrahydroporphyrins) and porphodimethenes (both 5,10- and 5,15-diphydrop

Poly(L-Glutamic Acid)-Drug Conjugates for Chemo- and Photodynamic Combination Therapy

Despite the polymeric vascular disrupting agent (poly(L-glutamic acid)-graft-methoxy poly(ethylene glycol)/combretastatin A4) nanoparticles can efficiently inhibit cancer growth, their further application is still a challenge owing to the tumor

Synthesis of unsymmetrical porphyrin dimers containing β-octaalkyl and meso-tetraphenylporphyrin subunits

Methodology for synthesis of phenyl-linked unsymmetrical dimers containing 8,12-diethyl 2,3,7,12,13,17,18-hexamethylporphyrin and meso-tetraphenylporphyrin subunits is reported. Hetero metal complexes of these dimers can be prepared by following two different routes.