16456-81-8

Basic information

• Product Name: 5,10,15,20-TETRAPHENYL-21H,23H-PORPHINE IRON(III) CHLORIDE
• Synonyms: 5,10,15,20-TETRAPHENYL-21H,23H-PORPHINE IRON(III) CHLORIDE;5,10,15,20-TETRAPHENYL-21H,23H-PORPHYRIN IRON(III) CHLORIDE;MESO-TETRAPHENYLPORPHYRIN IRON(III) CHLORIDE;MESO-TETRAPHENYLPORPHYRIN IRON(III) CHLORIDE COMPLEX;IRON TPP;IRON (III) MESO-TETRAPHENYLPORPHINE CHLORIDE;IRON (III) TETRAPHENYLPORPHINE CHLORIDE;RARECHEM AS SA 0004
• CAS NO: 16456-81-8
• Molecular Formula: C₄₄H₂₈ClFeN₄
• Molecular Weight: 704.02
• Product Categories: metal porphine (porphyrin) complex
• Mol File: 16456-81-8.mol
• Article Data: 39

Chemical Properties

• Melting Point: 300 °C
• Appearance: purple/crystal
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents, strong acids.
• CAS DataBase Reference: 5,10,15,20-TETRAPHENYL-21H,23H-PORPHINE IRON(III) CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10,15,20-TETRAPHENYL-21H,23H-PORPHINE IRON(III) CHLORIDE(16456-81-8)
• EPA Substance Registry System: 5,10,15,20-TETRAPHENYL-21H,23H-PORPHINE IRON(III) CHLORIDE(16456-81-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 16456-81-8(Hazardous Substances Data)

Usage

Chemical Properties

dark red or purple powder

Uses

Iron(III) meso-tetraphenylporphine chloride is used catalyzing reagent for silylation reactions.

Purification Methods

Purify it by extraction from a thimble (Soxhlet) with CHCl3. Concentrate the extract to ca 10mL and add ca 80mL of hot MeOH. Dark blue crystals separate on cooling. It can be recrystallised several times from CHCl3/MeOH. Avoid prolonged heating. It is quite soluble in organic solvents but insoluble in pet ether. [Rothemund & Manotti J Am Chem Soc 70 1808 1948, UV: Dorough et al. J Am Chem Soc 73 4315 1951, Beilstein 26 III 1960.]

InChI:InChI=1/C44H28N4.ClH.Fe/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;;/h1-28H;1H;/q-2;;+3/p-1/b41-33-,42-35-,43-38-,44-40-;;/rC44H28ClFeN4/c45-46-47-33-21-23-35(47)42(30-15-7-2-8-16-30)37-25-27-39(49(37)46)44(32-19-11-4-12-20-32)40-28-26-38(50(40)46)43(31-17-9-3-10-18-31)36-24-22-34(48(36)46)41(33)29-13-5-1-6-14-29/h1-28H

Upstream product

• 917-23-7 5,15,10,20-tetraphenylporphyrin 
• 917-23-7 5,10,15,20-tetraphenyl-21H,23H-porphine 
• 109-97-7 pyrrole 
• 100-52-7 benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 7789-46-0 iron(II) bromide 
• 1164142-04-4 (4-azo-(phenylcyanamido)benzene)(tetraphenylporphyrinato)iron(III) 
• 7705-08-0 iron(III) chloride 
• 75249-87-5 [Fe((C₆H₅)4C₂₀H₈N₄)]2C*2H₂O 
• 72347-08-1 (5,10,15,20-tetraphenylporphinato)iron(II)-(C(Cl)SeCH₂C₆H₅)*H₂O 
• 16887-00-6 chloride 

Downstream Products

• 25482-26-2 5,10,15,20-tetraphenyl porphyrinato iron hydroxide 
• 66746-94-9 carbonyl(meso-tetraphenylporphyrinato)iron(II) 
• 16591-56-3 5,10,15,20-tetraphenyl porphyrin iron 
• 165605-12-9 [(5,10,15,20-tetraphenylporphyrinato)Fe(THF)2]ClO₄ 
• 79197-95-8 (tetraphenylporphyrin)Fe(CH₃) 
• 57715-43-2 5,10,15,20-tetraphenylporphyrin iron(III) perchlorate 
• 87621-56-5 (tetraphenylporphyrin)Fe(p-MeC₆H₅) 
• 52674-29-0 (nitrosyl)(meso-tetraphenylporphyrinato)iron(II) 
• 102494-81-5 Fe((C₆H₅)4C₂₀H₈N₄)(NO₂)2^(1-) 
• 50262-98-1 (TPP)Fe(NO)Cl 
• 89165-46-8 (5,10,15,20,-tetraphenylporphinato)bis(tri-n-butylphosphine)iron(II) 
• 1164142-04-4 (4-azo-(phenylcyanamido)benzene)(tetraphenylporphyrinato)iron(III) 

Relevant articles and documents

Electrochemical analysis of iron-porphyrin-catalyzed CO2 reduction under photoirradiation

In this study, the photochemical reaction of a metal-complex-based catalyst was analyzed by electrochemical measurements. A well-known catalyst for the CO2 reduction reaction, meso-tetraphenylporphyrin iron(III) chloride (Fe(tpp)Cl), was selected as the target analyte. Although the analysis of the electrochemical response of Fe(tpp)Cl under photoirradiation with conventional cyclic voltammetry (CV) was not allowed, the adaptation of thin layer cyclic voltammetry (TLCV) enabled us to detect the photochemical reaction of Fe(tpp)Cl. The influence of photoirradiation on the electrochemical property of Fe(tpp)Cl was investigated both under Ar and CO2 atmospheres. Although the thin layer cyclic voltammograms of Fe(tpp)Cl upon photoirradiation under an Ar atmosphere were almost the same as those measured in the dark, the measurements under a CO2 atmosphere clearly indicated the change of the electrochemical response upon photoirradiation. The detailed analysis of this phenomenon revealed that the photoinduced decarbonylation reaction regenerates the original [FeII(tpp)] complex under photoirradiation.

Immobilization of Fe, Mn and Co tetraphenylporphyrin complexes in MCM-41 and their catalytic activity in cyclohexene oxidation reaction by hydrogen peroxide

Metalloporphyrin catalysts are able to carry out selective oxidation of organic substrates with several oxidizing agents. Recently, mesoporous materials have been studied as supports because they present high specific surface area, better dispersion and regeneration properties. This work presents the results of synthesis, characterization and application of three metalloporphyrin catalysts (FeTPPCl, MnTPPCl and CoTPP, where TPP = tetraphenylporphyrin) anchored on MCM-41, in the reaction of cyclohexene oxidation with hydrogen peroxide. A modified sol-gel preparation was chosen for the synthesis of the MCM-41 mesoporous material, as well as the anchoring was followed by Soxhlet extraction to ensure strong adsorption of the complex. The supported materials were much more stable than pure metalloporphyrins. The synthesized catalysts were characterized by UV-vis, FTIR, XRD, ICP-AES, 29Si MAS-NMR and thermal analysis, before and after incorporation. Evidence of the metalloporphyrin immobilization was confirmed by elemental analysis and their activity in the oxidation reaction. FeTPPCl/MCM-41 showed higher conversion than CoTPP/MCM-41 and MnTPPCl/MCM-41. However, MnTPPCl/MCM-41 even in low concentration on the support showed a good conversion for the direct oxidation of cyclohexene with the highest turnover number (1.54 × 105). All catalysts showed similar selectivity that favors allylic oxidation products over epoxidation. No leaching of the metalloporphyrins was observed after the reaction.

Formation of a complex with a carbide bridge between two iron atoms from the reaction of (tetraphenylporphyrin)iron(II) with carbon tetraiodide

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Dioxygen Activation in the Photochemistry of some Oxo-metalloporphyrin Complexes

Ultraviolet irradiation of the peroxo-complexes and (tpp = 5,10,15,20-tetraphenylporphyrinate) induces elimination of O2 and generation of the corresponding oxometalloporphyrins and .Reductive elimination o

Syntheses and CO2 reduction activities of π-expanded/extended iron porphyrin complexes

The construction of molecular catalysts that are active toward CO2 reduction is of great significance for designing sustainable energy conversion systems. In this study, we aimed to develop catalysts for CO2 reduction by introducing

Synthesis and Electrocatalytic CO2Reduction Activity of an Iron Porphyrin Complex Bearing a Hydroquinone Moiety

An iron porphyrin complex bearing a hydroquinone moiety at the meso position was newly designed and synthesized. Electrochemical analysis revealed that it catalyzes CO2reduction at a lower overpotential compared with an iron complex without a hydroquinone moiety. Experimental and theoretical investigation suggested that a hydroquinone moiety at the meso position stabilizes the coordination bond between the metal center and CO2via a hydrogen bond interaction with the latter in the secondary coordination sphere.