14172-91-9

Basic information

• Product Name: COPPER TPP
• Synonyms: RARECHEM AS SA 0003;PROTOPORPHYRIN IX CU(II);COPPER TPP;5,10,15,20-TETRAPHENYLPORPHYRIN CU(II);5,10,15,20-TETRAPHENYL-21H,23H-PORPHINE COPPER(II);5,10,15,20-TETRAPHENYL-21H,23H-PORPHINE COPPER (II) COMPLEX;[5,10,15,20-Tetraphenylporphinato(2-)]copper;21H,23H-Porphine, 5,10,15,20-tetraphenyl-, copper complex
• CAS NO: 14172-91-9
• Molecular Formula: C₄₄H₂₈CuN₄
• Molecular Weight: 676.27
• EINECS: 238-019-3
• Mol File: 14172-91-9.mol
• Article Data: 71

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: COPPER TPP(CAS DataBase Reference)
• NIST Chemistry Reference: COPPER TPP(14172-91-9)
• EPA Substance Registry System: COPPER TPP(14172-91-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 14172-91-9(Hazardous Substances Data)

Usage

General Description

Copper TPP, also known as copper triphenylphosphine, is a coordination compound that contains a copper atom bonded to three triphenylphosphine ligands. It is used as a catalyst in organic synthesis reactions, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. Copper TPP is known for its ability to promote C-C bond forming reactions, such as the coupling of aryl halides with terminal alkynes, and is widely utilized in the pharmaceutical and agrochemical industries for the synthesis of complex organic molecules. Additionally, copper TPP has been studied for its potential application in the development of new materials and nanotechnologies due to its unique electronic and optical properties.

InChI:InChI=1/C44H30N4.Cu/c1-5-13-29(14-6-1)38-27-37-26-35-22-21-33(45-35)25-34-23-24-36(46-34)28-39-40(30-15-7-2-8-16-30)41(31-17-9-3-10-18-31)44(48-39)42(43(38)47-37)32-19-11-4-12-20-32;/h1-28,45,48H;/q;+2/b33-25-,34-25-,35-26-,36-28-,37-26-,39-28-,43-42-,44-42-;

Upstream product

• 917-23-7 5,10,15,20-tetraphenyl-21H,23H-porphine 
• 92396-64-0 (N-ethyl-5,10,15,20-tetraphenylporphinato)copper(II) trifluoromethanesulfonate 
• 111-92-2 dibutylamine 
• 13014-03-4 copper 8-hydroxyquinolinate 
• 10380-28-6 bis(8-hydroxyquinolato)copper(II) 
• 14977-07-2 5,10,15,20-tetraphenylporphyrinato cadmium(II) 
• 790170-59-1 Cu(II)(adenine)2Cl₂ 
• 63904-13-2 (Cu(II)(adenine)Cl₂)2 
• 179032-09-8 copper tetraphenylporphyrin benzene solvate 
• 917-23-7 5,15,10,20-tetraphenylporphyrin 

Downstream Products

• 71147-55-2 (2-nitro-5,10,15,20-tetraphenylporphyrinato)copper(II) 
• 28132-68-5 copper(II) 5,10,15,20-tetraphenylporphyrin 
• 71763-49-0 copper(II) 2-formyl-5,10,15,20-tetraphenylporphyrin 
• 71147-55-2 Cu(2+)-nitro-α,β,γ,δ-tetraphenylporphine 
• 71159-98-3 2-Formyl-21,23-dihydro-5,10,15,20-tetraphenylporphyrin 

Relevant articles and documents

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Copper based macromolecular catalysts for the hydroxylation of phenols

Copper containing macromolecules, viz., Copper-meso-tetrakis-(4-carboxyphenyl)porphyrin (CuTCPP) and Copper-meso-tetra-phenylporphyrin (CuTPP) complexes were synthesized and heterogenized on the surface of aminated SBA-15 molecular sieves. The 1H NMR, mass spectral and elemental (CHN) analyses were performed to confirm the formation of these copper complexes (CuTCPP and CuTPP). The absence of 1H NMR signal, characteristic of N[sbnd]H bond (-2.79 ppm in TCPP and -2.74 ppm in TPP) in CuTCPP and CuTPP clearly confirms the incorporation of copper ion in to the cavities of the TCPP and TPP ligands. In addition, the decreased intensity of the soret band and the reduction of the number of Q bands also supports the formation of copper complexes. Further the homogeneous CuTCPP and CuTPP were grafted on the amino functionalized SBA-15. The grafting of copper complexes on amino functionalised SBA-15 was evident from the surface area analysis, powder XRD and N2 sorption isotherm. In the powder XRD, the shift in 2θ value compared to parent SBA-15 materials, and the broadening of the signal supports the grafting of copper complexes in to the amino functionalized SBA-15. Both homogeneous and heterogeneous copper macromolecular complexes were used as catalysts for the hydroxylation of phenolic compounds. The catalysts showed comparable conversion (72%) with the formation of ortho- and para- substituted products which have industrial importance. The hydroxylation reaction using the copper based macromolecular catalyst was found to be first order with an activation energy of 26.03 KJ/mol. Subsequently various substituted phenolic compounds, anisole and benzene also yielded the corresponding hydroxylated product with comparable conversion.

Reactions of Chelate Complexes with Macrocyclic Ligands. Octaphenyltetraazaporphine and Its Derivatives

Coordination of three azaporphines, namely, octaphenyltetraazaporphine (I), octa(4-nitrophenyl)-tetraazaporphine (II), and octa(4-bromophenyl)- tetraazaporphine (III) with some chelate salts of copper and zinc (hydroxyquinolate (IV), α-nitroso-β-naphthola

A non-covalent functionalization of copper tetraphenylporphyrin/chemically reduced graphene oxide nanocomposite for the selective determination of dopamine

A non-covalent functionalization based on a copper tetraphenylporphyrin/chemically reduced graphene oxide (Cu-TPP/CRGO) nanocomposite is demonstrated for selective determination of dopamine (DA) in pharmaceutical and biological samples. A homogeneous electron-rich environment can be created on the graphene surface by Cu-TPP due to the π-π non-covalent stacking interaction. The synthesized Cu-TPP/CRGO nanocomposite was characterized using scanning electron microscopy NMR, ultraviolet-visible and electrochemical impedance spectroscopies. The electrocatalytic activity of DA was evaluated using cyclic voltammetry and differential pulse voltammetry. The oxidation peak current (Ipa) of DA increased linearly with increasing concentration of DA in the range 2-200 μM. The detection limit was calculated as 0.76 μM with a high sensitivity of 2.46 μA μM-1 cm-2. The practicality of the proposed DA sensor was evaluated in DA hydrochloride injection, human urine and saliva, and showed satisfactory recovery results for the detection of DA. In addition, the Cu-TPP/CRGO nanocomposite-modified electrode showed excellent stability, repeatability and reproducibility towards the detection of DA.

Tuning the crystal structures of metal-tetraphenylporphines: Via a magnetic field

In this work, two new single crystals of copper-tetraphenylporphine (Cu-TPP) (crystals 2 and 3), which were induced by external magnetic fields with strengths of 0.5 and 0.8 T, respectively, have been prepared and characterized by single-crystal X-ray diffraction and Hirshfeld surface analysis. Compared with the original Cu-TPP (crystal 1), crystals 2 and 3 exhibit significant differences in their unit cell parameters, crystalline stacking styles and intermolecular interactions, resulting in a compressed crystal packing. Here, the number of closer interactions (H?H, C?H/H?C) increased with the magnetic field strength, accompanied by a decrease in the number of π?π (C?C) interactions as a sacrifice. On considering the results of our previous work, the results here suggest that a magnetic field has a different influence on the crystallization process of mono-component and multi-component materials, which will certainly provide some suggestions for the design of crystallization strategies for other materials with the presence of an external magnetic field.

Ligand exchange in the complexone-porphyrin macrocycle system in reactions of copper(II) ethylenediaminetetraacetate with porphyrins and phthalocyanines

Complexation between 5,10,15,20-tetraphenylporphine H2TPP and tetra(tert-butyl)phthalocyanine H2(t-Bu)4Pc with copper(II) ethylenediaminetetraacetate in DMSO was studied by spectrophotometry. The kinetic parameters of the

The redox chemistry of copper tetraphenylporphyrin revisited

Mixing Cu(II)Cl2 with free base tetraphenylporphyrin ((H 2(TPP)) in dry deaerated 1,2-dichloroethane surprisingly yields a mixture of Cu(II)(TPP) and Cu(III)(TPP). The later is long-lived in the absence of water and slowly decomposes within days to yield Cu(II)(TPP). Furthermore, in the presence of air, a slightly different CuIII porphyrin species forms, presumably, Cu(III)(TPP)?+, in which the Q-band is subject to a 10 nm red shift. The new Cu(III)(TPP) and Cu(III)(TPP) ?+ differ in terms of absorption, fluorescence, electron paramagnetic resonance (EPR), and X-ray photoemission spectroscopy (XPS) when compared to the well-characterized Cu(II)(TPP), Cu(II)(TPP)?+, and Cu(II)(TPP)2+ species.

Reactions in detergentless microemulsions: Incorporation of copper(II) into meso-tetraphenylporphine ((TPP)H2) in a water/oil microemulsion

The rate of incorporation of Cu(II) into tetraphenylporphine has been followed in ternary solvent systems consisting of water, toluene, and 2-propanol. Studies carried out in microemulsions at pH 3 show that when the surfactants hexadecyltrimethylammonium perchlorate and hexadecylpyridinium perchlorate are added, little or no change in rate from that observed in detergent-free systems occurs. When the surfactant anion is Cl- or Br-, there is a marked increase in rate (ClO4- ? Cl- -). Addition of the anionic surfactant sodium hexadecyl sulfate and the nonionic Alfonic 1412-60 has little effect on the rate of reaction. A study of the rate of metalation as a function of solvent composition shows an increase in rate in the small-aggregate and normal ternary solution regions.

Reactions of chelates with macrocyclic ligands. Complexation between tetraphenylporphine and Cu(II) complexes with α-amino acids

The reactions of tetraphenylporphine (H2TPP) with copper(II) chelates in DMSO were studied. α-Amino acids (glycine, α-alanine, valine, leucine, tyrosine, and glutamine) were used as chelating ligands. The study of the reaction kinetics showed that Cu(II) chelates with alanine and the other amino acids are less reactive in these reactions than acetylacetonates, α-nitroso-β-naphtholates, and hydroxyquinolates. The exception is a Cu(II) complex with tyrosine. The relationship between the structure of the above chelates and the rate of their reactions with porphyrin was determined.

Modern methods for the sustainable synthesis of metalloporphyrins

Metalloporphyrins are involved in many and diverse applications that require the preparation of these compounds in an efficient manner, which nowadays, also involves taking into consideration sustainability issues. In this context, we use ball milling mechanochemistry and sonochemistry for the rational development of synthetic strategies for the sustainable preparation of metalloporphyrins. Zinc, copper, cobalt and palladium complexes of hydrophobic porphyrins were obtained in high yields and under mechanical action with a moderate excess of the metal salt, without any solvent or additive. Sonochemistry prove to be a good alternative for the preparation of metal complexes of water-soluble porphyrins in good yields and short reaction times. Both strategies have good sustainability scores, close to the ideal values, which is useful in comparing and helping to choose the more adequate method.

Single-atom metal-N4site molecular electrocatalysts for ambient nitrogen reduction

Electrochemical N2reduction to NH3is an emerging energy technology, attracting much attention due to its features of mild reaction conditions and being non-polluting. In this work, we demonstrate that a well-defined cobalt tetraphenylporphyrin (CoTPP) molecule as a model catalyst exhibits good electrocatalytic nitrogen reduction activity in 0.1 M HCl electrolyte with an ammonia yield of 15.18 ± 0.78 μg h-1mg-1cat.calculated by the indophenol blue method and a Faraday efficiency (FE) of 11.43 ± 0.74%. The catalyst also has satisfactory electrolytic stability and recycling test reusability. The activity displayed by the porphyrin molecular catalysts is attributed to the full exposure of the metal-N4sites. To trace the source of ammonia, an isotope labeling experiment (15N2as the feed gas) is used to calculate the ammonia yieldvia1H nuclear magnetic resonance (NMR), which is close to that of the indophenol blue method. In addition, we replace the central metal to prepare CuTPP and MnTPP, and they also show electrocatalytic nitrogen reduction reaction (NRR) ability. This work proves the feasibility and versatility of using metalloporphyrin molecules as model electrocatalysts for NRR and offers a new strategy for the further development of molecular NRR catalysts.

Method for synthesizing copper porphyrin from aromatic aldehyde, pyrrole and copper salt

The invention discloses a method for synthesizing copper porphyrin from aromatic aldehyde, pyrrole and copper salt. Under the catalysis of anhydrous aluminum trichloride, aromatic aldehyde, pyrrole and copper salt are refluxed in a DMF solvent to generate tetraaryl copper porphyrin through a one-pot reaction. The reaction process comprises the following steps: sequentially adding the anhydrous aluminum trichloride, aryl aldehyde, the pyrrole and the copper salt into DMF while stirring, stopping reaction after heating reflux reaction for a certain period of time, cooling, standing overnight near 273K, and carrying out suction filtration to obtain copper porphyrin crystals. According to the method, the aromatic aldehyde, the pyrrole and the copper salt are directly used as raw materials, porphin is not needed, strongly corrosive organic acid is not used as a solvent, high-purity tetraaryl copper porphyrin is obtained at a high yield under the condition that a complex separation means isnot needed, and industrial production is easy to achieve.