22112-77-2

Basic information

• Product Name: meso-Tetra (4-chlorophenyl) porphine
• Synonyms: meso-Tetra (4-chlorophenyl) porphine;21H,23H-Porphine, 5,10,15,20-tetrakis(4-chlorophenyl)-;5,10,15,20-tetrakis(4-chlorophenyl)-21,22-dihydroporphyrin;5,10,15,20-tetrakis(para-chlorophenyl)porphyrin;H2t(4-Cl)pp;meso-tetrakis-(4-chlorophenyl)porphyrin;tetra(para-chlorophenyl)porphyrin;TPP(4-Cl)4
• CAS NO: 22112-77-2
• Molecular Formula: C₄₄H₂₆Cl₄N₄
• Molecular Weight: 752.51604
• Mol File: 22112-77-2.mol

Chemical Properties

• Melting Point: >27 °C
• Appearance: /
• Density: 1.398g/cm³
• Refractive Index: 1.702
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: meso-Tetra (4-chlorophenyl) porphine(CAS DataBase Reference)
• NIST Chemistry Reference: meso-Tetra (4-chlorophenyl) porphine(22112-77-2)
• EPA Substance Registry System: meso-Tetra (4-chlorophenyl) porphine(22112-77-2)

Safety Data

• Hazardous Substances Data: 22112-77-2(Hazardous Substances Data)

Usage

Uses

Used in Photodynamic Therapy:
Meso-tetra(4-chlorophenyl)porphine is used as a photosensitizer in photodynamic therapy for its ability to selectively destroy cancer cells when activated by light. Its light-sensitive properties make it a promising candidate for the treatment of various types of cancer.
Used in Chemical Sensors:
Meso-tetra(4-chlorophenyl)porphine is utilized as a sensing material in chemical sensors due to its ability to interact with specific chemical species, allowing for the detection and measurement of various compounds.
Used in Catalysis:
In the field of catalysis, meso-tetra(4-chlorophenyl)porphine serves as a catalytic agent, leveraging its chemical properties to facilitate and enhance the rate of chemical reactions.
Used as a Model System in Research:
Meso-tetra(4-chlorophenyl)porphine is used as a model system for studying the properties of natural porphyrin compounds, providing insights into their behavior and potential applications in various scientific and industrial fields.
Used in the Synthesis of Porphyrin Derivatives:
Meso-tetra(4-chlorophenyl)porphine is employed as a starting material in the synthesis of other porphyrin derivatives, which are then used for further research and industrial applications, expanding the scope of porphyrin-based compounds in diverse sectors.

InChI:InChI=1/C44H26Cl4N4/c45-29-9-1-25(2-10-29)41-33-17-19-35(49-33)42(26-3-11-30(46)12-4-26)37-21-23-39(51-37)44(28-7-15-32(48)16-8-28)40-24-22-38(52-40)43(36-20-18-34(41)50-36)27-5-13-31(47)14-6-27/h1-24,49,52H/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-

Upstream product

• 109-97-7 pyrrole 
• 104-88-1 4-chlorobenzaldehyde 
• 154047-16-2 (4-Chloro-phenyl)-(1H-pyrrol-2-yl)-methanol 
• 121-33-5 vanillin 
• 137018-26-9 2,2'-((4-chlorophenyl)methylene)bis(1H-pyrrole) 
• 248606-50-0 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinogen 
• 275-51-4 azulene 
• 13169-71-6 2-(4-chlorobenzoyl)pyrrole 
• 7099-88-9 4-chlorophenylglyoxylic acid 
• 99-91-2 para-chloroacetophenone 
• 22112-84-1 tetrakis(4-aminophenyl)porphyrin 

Relevant articles and documents

Insights into the new cadmium(II) metalloporphyrin: Synthesis, X-ray crystal structure, Hirshfeld surface analysis, photophysical and cyclic voltammetry characterization of the (morpholine){(meso-tetra(para-chloro-phenyl)porphyrinato}cadmium(II)

In this work we report the synthesis of the cadmium(II)-meso-tetra(para-chloro-phenyl)porphyrin with the morpholine O-donor axial ligand with formula [Cd(TClPP)(morph)] (I). This coordination compound adopts a distorted five-coordinate square pyramidal ge

UV–visible and fluorescence spectroscopic assessment of meso?tetrakis?(4?halophenyl) porphyrin; H2TXPP (X = F, Cl, Br, I) in THF and THF-water system: Effect of pH and aggregation behaviour

The current study determines optical and fluorescence response of halogen substituted series of meso?tetrakis?(4?halophenyl) porphyrin; H2TXPP (Halo = F, Cl, Br, I) dye in tetrahydrofuran; THF and THF-water system at changing pH in relationship with changing medium of allure. Effects produced by varying the pH and medium, over spectral and aggregation were discussed in detail. Results show sequential protonation and deprotonation of H2TXPP series in acidic (pH = 4) and (pH =10) basic medium. Specific structural changes of monomeric absorption band were put in evidence on lowering pH, which includes broadening and splitting of soret or B band. Other changes include increasing in intensity and red-shifting of Q1 band indicating some degree of aggregation. The side-by-side aggregation and formation of J-aggregate were quite evident. The red shift of B band featured self-aggregation through head-to-tail molecular ordering which is consonant with absorption-emission data.

A One-Step Route to CO2-Based Block Copolymers by Simultaneous ROCOP of CO2/Epoxides and RAFT Polymerization of Vinyl Monomers

The one-step synthesis of well-defined CO2-based diblock copolymers was achieved by simultaneous ring-opening copolymerization (ROCOP) of CO2/epoxides and RAFT polymerization of vinyl monomers using a trithiocarbonate compound bearin

Synthesis of novel single site tin porphyrin complexes and the catalytic activity of tin tetrakis(4-fluorophenyl)porphyrin over -caprolactone

Tin tetrakis(4-fluorophenyl)porphyrin, tin tetrakis(4-chlorophenyl)porphyrin and tin tetrakis(4-bromophenyl)porphyrin complexes were prepared by reaction of butyltin trichloride with tetrakis(4-fluorophenyl)porphyrin, tetrakis(4-chlorophenyl)porphyrin, and tetrakis(4-bromophenyl)porphyrin in tetrahydrofuran and toluene, respectively. These novel complexes were characterized by 1H, 13C NMR, FTIR, mass spectroscopy and elemental analysis. The single site tin complex including fluoride was tested as a catalyst in polymerization of -caprolactone and was very effective. Polycaprolactone was characterized by 1H, 13C NMR, and gel permeation chromatography.

Synthesis and single crystal structure of a new polymorph of 5, 10, 15, 20-tetrakis-(4-chlorophenyl) porphyrin, H2TTPCl4: Spectroscopic investigation of aggregation of H2TTPCl4

5, 10, 15, 20-tetrakis-(4-chlorophenyl) porphyrin, H2TTPCl4, has been isolated as a new polymorph following the modified Adler’s method and its X-ray crystal structure solved. The new polymorph (I) crystallises in the monoclinic spac

PH-switchable porphyrin receptor for binding halide ions

Main properties of 5,10,15,20-tetra(4-chlorophenyl)porphyrin in the acetonitrile-perchloric acid system were studied by the method of spectrophotometric titration at standard temperature. The protonation of nitrogen atoms of the tetrapyrrole macrocycle wa

Preparation of a porphyrin-polyoxometalate hybrid and its photocatalytic degradation performance for mustard gas simulant 2-chloroethyl ethyl sulfide

By combining 5,10,15,20-tetra(4-chlorine)phenylporphyrin (TClPP) and α-Keggin polyoxometalate H5PV2Mo10O40 (H5PVMo) via a simple ion-exchange method, an organic-inorganic hybrid material [C44H28N4Cl4]1.5[H2PMo10V2O40]·2C2H6O (H2TClPP-H2PVMo) was prepared and thoroughly characterized by a variety of techniques. The homogeneous photocatalytic degradation of 2-chloroethyl ethyl sulfide (CEES) (5 μL) by H2TClPP-H2PVMo (1 × 10?6 mol/L) was studied in methanol and methanol-water mixed solvent (v/v = 1:1), in which the degradation rate of CEES reached 99.52% and 99.14%, respectively. The reaction followed first-order reaction kinetics, and the half-life and kinetic constant in methanol and the mixed solvent were respectively 33.0 min, ?0.021 min?1 and 15.7 min, ?0.043 min?1. Mechanism analysis indicated that under visible light irradiation in the air, CEES was degraded via oxidation and alcoholysis/hydrolysis in methanol and the mixed solvent. O2·? and 1O2 generated by H2TClPP-H2PVMo selectively oxidized CEES into a nontoxic sulfoxide. Singlet oxygen capture experiments showed that H2TClPP-H2PVMo (? = 0.73) had a higher quantum yield of singlet oxygen than TClPP (? = 0.35) under an air atmosphere and visible light irradiation.

Efficient oxidation of cycloalkanes with simultaneously increased conversion and selectivity using O2 catalyzed by metalloporphyrins and boosted by Zn(AcO)2: A practical strategy to inhibit the formation of aliphatic diacids

The direct sources of aliphatic acids in cycloalkanes oxidation were investigated, and a strategy to suppress the formation of aliphatic acids was adopted through enhancing the catalytic transformation of oxidation intermediates cycloalkyl hydroperoxides to cycloalkanols by Zn(II) and delaying the emergence of cycloalkanones. Benefitted from the delayed formation of cycloalkanones and suppressed non-selective thermal decomposition of cycloalkyl hydroperoxides, the conversion of cycloalkanes and selectivity towards cycloalkanols and cycloalkanones were increased simultaneously with satisfying tolerance to both of metalloporphyrins and substrates. For cyclohexane, the selectivity towards KA-oil was increased from 80.1% to 96.9% meanwhile the conversion was increased from 3.83 % to 6.53 %, a very competitive conversion level with higher selectivity compared with current industrial process. This protocol is not only a valuable strategy to overcome the problems of low conversion and low selectivity lying in front of current cyclohexane oxidation in industry, but also an important reference to other alkanes oxidation.

Spectroscopic characterization, X-ray molecular structures and cyclic voltammetry study of two (piperazine) cobalt(II) meso-arylporphyin complexes. Application as a catalyst for the degradation of 4-nitrophenol

Two new cobaltous-porphyrin complexes, namely (μ-piperazine)-bis[(meso-tetra(para-methoxyphenyl)porphyrinato)]cobalt(II) and (piperazine)[meso-tetra(para-chlorophenyl)porphyrin]cobalt(II) dichloromethane disolvate, with the formulas [{CoII(TMPP)}2(μ2-pipz)] (complex 1) and [CoII(TClPP)(pipz)]·2CH2Cl2 (complex 2), were used efficiently as catalysts in the degradation of 4-nitrophenol (4-NP) in an aqueous hydrogen peroxide solution. These cobalt(II)-pipz porphyrin complexes were characterized by a variety of spectroscopic methods including infrared, UV–visible, fluorescence, proton nuclear magnetic resonance, electron paramagnetic resonance (EPR) as well as mass spectrometry. A cyclic voltammetry investigation was also carried out on these two Co(II) metalloporphyrins. The EPR results indicate that both complexes 1 and 2 are paramagnetic low-spin (S = 1/2) cobalt(II) porphyrin complexes. Furthermore, the X-ray diffraction crystal structures of 1 and 2 were determined, and the intermolecular interactions were investigated by Hirshfeld surface analysis.

K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins

The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.