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CAS No. : | 917-23-7 | MDL No. : | MFCD00011680 |
Formula : | C44H30N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YNHJECZULSZAQK-UHFFFAOYSA-N |
M.W : | 614.74 | Pubchem ID : | 86280046 |
Synonyms : |
TPP;Tetraphenylporphine;meso-Tetraphenylporphyrin
|
Num. heavy atoms : | 48 |
Num. arom. heavy atoms : | 34 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 203.47 |
TPSA : | 56.3 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -2.66 cm/s |
Log Po/w (iLOGP) : | 5.53 |
Log Po/w (XLOGP3) : | 10.41 |
Log Po/w (WLOGP) : | 7.23 |
Log Po/w (MLOGP) : | 4.98 |
Log Po/w (SILICOS-IT) : | 10.13 |
Consensus Log Po/w : | 7.66 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -10.47 |
Solubility : | 0.0000000208 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
Log S (Ali) : | -11.54 |
Solubility : | 0.0000000018 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
Log S (SILICOS-IT) : | -15.45 |
Solubility : | 0.0 mg/ml ; 3.56e-16 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 7.47 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; at 350.0℃; for 0.0666667h;Inert atmosphere; Sealed tube; | Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
400 mg | With acetic acid; In chloroform; for 2h;Reflux; | Copper tetraphenyl porphyrin was synthesised by taking tetra phenyl porphyrin[H2(TPP)]16(500mg) in chloroform(100ml).Copper(II) acetate(200mg) in glacial aceticacid(50ml) was added to the above solution andthe mixture was refluxed for 2hrs. The contents wereconcentrated to a volume of about 50-60ml andcooled to room temperature which resulted in crudecopper-tetraphenyl porphyrin Cu(TPP) (about450mg). The crude product was purified by columnchromatography using neutral alumina andchloroform as eluent. On elution the unreactedtetraphenyl porphyrin was eluted out first, followedby pure Cu(TPP). The chloroform fraction containingCu(TPP) was concentrated to obtain pure crystalsof Cu(TPP)[2]. The formation of Cu(TPP) wasmonitored by UV-visible spectroscopy which givepeaks-around 580, 541 and 417nm respectivelyconfirming the formation of Cu(TPP) (yield=400mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; at 350.0℃; for 0.0666667h;Inert atmosphere; Sealed tube; | Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; at 350.0℃; for 0.0666667h;Inert atmosphere; Sealed tube; | Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; at 350℃; for 0.0666667h;Inert atmosphere; Sealed tube; | Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.5% | In N,N-dimethyl-formamide; at 150.0℃; for 0.5h; | To a 250 mL round bottom flask equipped with a reflux condenser was charged 1.000 g (1.6 mmol) of 5,10,15,20-tetraphenylporphyrin and 100 ml of N, N-dimethylformamide (DMF) , Heated to reflux (about 154 ), until it is completely dissolved,A solution of 650 g (3.2 mmol) of copper acetate in 50 mL of DMF was added thereto, followed by reaction at 150 C using thin layer chromatography (developing solvent in a 1: 1 by volume mixture of chloroform and petroleum ether) After about 0.5 hours of reaction, the raw material point disappears and the reaction is complete. The reaction solution is poured into 100 mL of ice water while hot, allowed to stand for 30 min and then filtered. The solid is washed with ethanol and washed to the filtrate. The crude product was dried in a vacuum. The product was 1.010 g, yield 93.5%. |
86% | In N,N-dimethyl-formamide; for 0.00416667h;Reflux; | A mixture of 0.04 g (0.065 mmol) of porphin 1 and 0.118 g (0.65 mmol) of Cu(OAc)2 in 40 mL of dimethylformamide was heated under reflux for 15 s. The reaction mixture was cooled, water and solid NaCl was added, the precipitate was separated by filtration, washed with water, dried, and chromatographed on aluminum oxide using chloroform as an eluent to give 0.038 g (0.0562 mmol) (86%) of compound 5. MS (m/z (Irel, %)): 675 (97) [M]+; for C44H28N4Cu calcd.: 676. IR (nu, cm-1): 2926 s, 2855 m nu(C-H, Ph), 1694 w,1598 m 1489 s nu(C=C, Ph), 1441 m nu(C=N), 1371 m, 1346 s nu(C-N), 1146 s, 1071 s delta(C-H, Ph), 1005 s nu(C-C), 861 m, 794 m gamma(C-H, pyrrole ring), 742 m, 696 m gamma(C-H, h), 480 nu(Cu-N). |
0.04 g | In N,N-dimethyl-formamide; for 0.0333333h;Reflux; | 0.118 g (0.65 mmol) of Cu(OAc)2 was added to a solution of 0.04 g (0.065 mmol)of 2 in 50 mL of DMF. The reaction mixture was refluxed during 2 min and cooled to ambient; five-fold excess of water and NaCl was added. The precipitate was filtered off, washed with water, and dried. Yield 0.04 g (0.059 mmol) of CuTPP. |
With acetic acid; at 24.84℃;Kinetics; | General procedure: The reactions of complexing between porphyrins and copper acetate were studied by means of spectrophotometry in the range of 293-318 K. The change in temperature during the experiment did not exceed±0.1 K. | |
In N,N-dimethyl-formamide; at 44.84℃;Kinetics; Thermodynamic data; | General procedure: Porphyrins 1-6 (Aldrich, 97%), organic solvents (Merck, 99%), and inorganic salts (Acros, 99%) were used as received. The complex formation was studied by recording electronic absorption spectra of the solutions using a Cary 300 spectrophotometer (Varian). To do so,solutions of the studied porphyrin (2.5×10-5 mol/L)and the salt (2.5×10-3 mol/L) in an organic solvent were put in the cell maintained at constant temperature(±0.1C), and the absorbance at the wave length corresponding to the maximum in the spectrum of the formed metal porphyrinate was monitored. Kinetic studies of the complex formation were performed over 288-363 K range. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In N,N-dimethyl-formamide; for 0.00555556h;Heating; | 0.05 g (0.0813 mmol) of tetraphenylporphyrin and0.144 g (0.813 mmol) of Co(OAc)2 were dissolved in70 mL of DMF, heated to boiling, boiled for 20 s, andcooled. The filtrate was poured into water, theprecipitate was filtered off, washed with water, dried,and chromatographed on alumina using dichloromethaneas the eluent [25]. Yield 0.04 g (0.0595 mmol,72%), Rf 0.77 (1 : 1 hexane-chloroform). IR spectrum,nu, cm-1: 2917, 2849 (CH, Ph), 1694, 1599 (C=C, Ph),1437 (C=N), 1350 (C-N), 1150, 1073 [delta(C-H, Ph)],1004 (Co-N), 796 [gamma(C-H, pyrrole ring)], 752, 702[gamma(C-H, Ph)], 470 (Co-N). 1H NMR spectrum(CDCl3), delta, ppm: 16.05 br.s (8H, pyrrole), 13.20 br.s(8H, Ho), 8.20 t (8H, Hm, J = 7.7 Hz), 8.01 br.s (4H,Hn). Mass spectrum, m/z (Irel, %): 671.3 (99) [M - H]+(calculated for C44H28N4Co: 672). EAS (benzene),lambdamax, nm (log epsilon): 529 (4.16), 413 (5.35). Found, %: C78.58; H 4.15; N 8.30. C44H28N4Co. Calculated, %: C78.69; H 4.20; N 8.34. |
In N,N-dimethyl-formamide; at 89.84℃;Kinetics; Thermodynamic data; | General procedure: Porphyrins 1-6 (Aldrich, 97%), organic solvents (Merck, 99%), and inorganic salts (Acros, 99%) were used as received. The complex formation was studied by recording electronic absorption spectra of the solutions using a Cary 300 spectrophotometer (Varian). To do so,solutions of the studied porphyrin (2.5×10-5 mol/L)and the salt (2.5×10-3 mol/L) in an organic solvent were put in the cell maintained at constant temperature(±0.1C), and the absorbance at the wave length corresponding to the maximum in the spectrum of the formed metal porphyrinate was monitored. Kinetic studies of the complex formation were performed over 288-363 K range. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium acetate; potassium carbonate; In N,N-dimethyl-formamide; chlorobenzene; at 150℃; | General procedure: In a 250mL distillation flask, 5,10,15,20-tetraphenylporphyrin (H2TPP) (0.50g, 0.81mmol) and NaOAc (0.30g, 3.6mmol) was stirred in 75mL of chlorobenzene and 50mL of DMF. After the addition of two equivalents of metal acetate, a Soxhlet extractor with a cellulose filter thimble filled with ?3g of K2CO3 was attached to the distillation flask. The assembly was completed with a condenser on the top of the extractor; and then the mixture was heated to reflux at 150C overnight. The reaction extent was monitored by TLC or UV-Vis until all the H2TPP was consumed. After the reaction was compete, the solvent was removed under vacuum. The remaining solid was dissolved in 150mL of chloroform, and washed with water (50mL×3). The organic layer was further washed with a saturated sodium bicarbonate solution (50mL×3), and then dried over K2SO4. After removal of the solvent in vacuo, the solid was recrystallized from chloroform/heptane. |
87% | In N,N-dimethyl-formamide; for 0.166667h;Heating; | (5,10,15,20-tetraphenyl-21,23-porphinato)cobalt(II) (CoTPP) was prepared by reaction of 5,10,15,20-tetraphenyl-21,23-porphine (H2TPP) (50 mg, 0.081 mmol) with Co(AcO)2 · 4H2O (101 mg, 0.41 mmol) in boiling dimethylformamide (DMF) for 10 min. When the reaction was(as judged from the disappearance of H2TPP bands and the end of evolution of the electronic absorption spectrum (UV-vis spectrum) of a reaction mixture sample in chloroform) the contents of the reaction flask were cooled and the products were extracted into chloroform after dilution with water. The solution in CHCl3 was repeatedly washed with distilled water to remove DMF. The CHCl3 was partially distilled off; the residual solution was purified by chromatography on an Al2O3-packed column (grade II activity according to Brockman) using chloroform. CoTPP yield: 87%. UV-vis spectrumin toluene (lambdamax nm, (logepsilon)): 413 (5.35), 529 (4.38). IR spectrum in KBr (nu, cm-1): 415, 467, 527, 557, 567, 621, 650, 671, 700, 716, 751, 797, 835, 846, 900, 923, 997, 1005, 1020, 1071, 1155, 1178, 1205, 1236, 1309, 1350, 1441, 1492, 1540, 1576, 1599, 2852, 2922, 3025, 3052. 1H NMR in CDCl3 (delta, ppm): 9.83 (m, 12Hm,p), 13.16 (br. s, 8H),15.94 (br. s, 8Hbeta). 13CNMR in CDCl3 (delta, ppm): 157.59, 141.79, 131.38, 130.92, 99.61. MS (MALDI-TOF) (m/z): 671.25 [M]+. |
1.7 kg | With potassium carbonate; In N,N-dimethyl-formamide; chlorobenzene; at 150℃;Large scale; | In a 1000 L metallization reactor, a mixed solvent of 250 L of chlorobenzene and 160 L of N,N-dimethylformamide (DMF) was added. Stirring was started by adding 5,10,15,20-tetraphenylporphyrin (H2TPP) at 1.7 kg. Finally, add two equivalents of cobalt acetate tetrahydrate (Co(OAc)2*4H2O) 1.33kg, then, about 12 kg of potassium carbonate (K2CO3) is charged into the alkali storage chamber. The mixture in the reactor was heated to 150 C and kept under reflux. The progress of the reaction was then monitored by thin layer chromatography (TLC) or UV-Vis absorption spectroscopy (UV-Vis) until the complete reaction of H2TPP was completed. The solvent was distilled off under vacuum and the remaining solid was dissolved in 600 L of chloroform. Wash three times with water 150L, then collect these liquids for static stratification. Drying the organic layer with molecular sieves, The solvent is distilled off under vacuum, The remaining solid was recrystallized from chloroform/heptane. A pink purple crystalline solid product, cobalt porphyrin, 1.7 kg was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In ethanol; dichloromethane;Reflux; | meso-Tetraphenylporphyrin (TPP)(2 g, 3.25 mmol) was dissolved in CH2Cl2 (160 mL) and methanol (50 mL). Cu(OAc)2·H2O (1.2 g,5.85 mmol) was added and the mixture was heated to reflux for 2 h until all starting material wasconsumed (TLC, UV-vis). Solvents were evaporated to give a red-purple residue that was filteredthrough a short plug of silica. After filtration, the product 3 was obtained as a dark purple sparklingsolid (2.2 g, 3.25 mmol, 99%) |
96% | With sodium acetate; potassium carbonate; In N,N-dimethyl-formamide; chlorobenzene; at 150.0℃; | General procedure: In a 250mL distillation flask, 5,10,15,20-tetraphenylporphyrin (H2TPP) (0.50g, 0.81mmol) and NaOAc (0.30g, 3.6mmol) was stirred in 75mL of chlorobenzene and 50mL of DMF. After the addition of two equivalents of metal acetate, a Soxhlet extractor with a cellulose filter thimble filled with ?3g of K2CO3 was attached to the distillation flask. The assembly was completed with a condenser on the top of the extractor; and then the mixture was heated to reflux at 150C overnight. The reaction extent was monitored by TLC or UV-Vis until all the H2TPP was consumed. After the reaction was compete, the solvent was removed under vacuum. The remaining solid was dissolved in 150mL of chloroform, and washed with water (50mL×3). The organic layer was further washed with a saturated sodium bicarbonate solution (50mL×3), and then dried over K2SO4. After removal of the solvent in vacuo, the solid was recrystallized from chloroform/heptane. |
96% | With potassium carbonate; In N,N-dimethyl-formamide; chlorobenzene; at 150.0℃; | A mixed solvent of 75 ml of chlorobenzene and 50 ml of N,N-dimethylformamide (DMF) was added to a 250 ml three-neck distillation flask. Add 5,10,15,20-tetraphenylporphyrin (H2TPP) (0.50 g, 0.81 mmol) start stirring, after the solid is dissolved, add an appropriate amount of copper acetate monohydrate (Cu(OAc)2*H2O) (0.324 g 1.62 mmol). Put about 3g of potassium carbonate (K2CO3) in the alkali storage chamber, the mixture in the reaction kettle was heated to 150 C and kept under reflux. The progress of the reaction (UV-Vis) is monitored by thin layer chromatography (TLC) or ultraviolet visible absorption spectroscopy until the complete reaction of H2TPP is completed. The solvent is distilled off under vacuum. The remaining solid was dissolved in 150 ml of chloroform. Wash three times with 50 ml of water each time, then collect these liquids in a static layer. The organic layer was further washed three times with 50 ml of saturated sodium bicarbonate solution. Then dried with potassium sulfate (K2SO4), The solvent is distilled off under vacuum. The remaining solid was recrystallized from chloroform/heptane. A purple crystalline solid product of 0.526 g was obtained in a yield of 96%. |
757 mg | In methanol; dichloromethane; at 20.0℃; for 1.5h;Inert atmosphere; | General procedure: A solution of Cu(OAc)2·H2O (4.6 mmol) in methanol (10 mL) was added to a solution of corresponding porphyrin (1.15 mmol) in methylene chloride (50 mL). The resulting mixture was stirred flor 1.5 h at room temperature with TLC monitoring (CHCl3-hexane 1:2). Then the reaction mixture was poured into water and extracted with methylene chloride. The organic layer was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was used without purification. 5,10,15,20-(tetraphenylporphyrinato)copper(II) (13) [56] (757 mg,yield 97%). UV-Vis (CH2Cl2) >max, (j10-3) nm: 414 (611), 539 (29).APCI-MS Found: [M]+ 676.16; ?C44H28CuN4? requires [M]+ 676.26. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With cadmium(II) chloride; In N,N-dimethyl-formamide; for 0.333333h;Reflux; | General procedure: a. A mixture of 0.02 g (0.0325 mol) of compound I in 40 mL of DMF and 0.082 g (0.650 mol) of MnCl2 was boiled during 80 min. The mixture was cooled down to ambient, diluted with water, and solid NaCl was added. The precipitate was filtered off, washed with water, and dried. Yield 0.0175 g (0.0249 mmol, 77%), Rf 0.76. b. A mixture of 0.02 g (0.0325 mmol) of compound I and 0.06 g (0.325 mmol) of CdCl2 in 40 mL of DMF was heated to boiling, and then 0.082 g (0.650 mmol) of MnCl2 was added. The mixture was boiled during 20 min and then treated as described in procedure a. Yield 0.018 g (0.0256 mmol, 80%), Rf 0.76. 1H NMR spectrum, delta, ppm: 8.30 br.s (16H, Ho,m, C6H5), 7.75 br.s (4H, Hp, C6H5). Found, %: C 74.95; H 3.94; N 7.88. C44H28ClMnN4. Calculated, %: 75.16; 4.01;N 7.97. (Cl)Mn(III) porphyrinates V and VI were prepared similarly. |
68% | In N,N-dimethyl-formamide;Reflux; | This precursor wasprepared according to the literature procedure of Feng et al.(2012). TPP (1.0 g, 1.6 mmol) was dissolved in DMF andMnCl2 (3.0 g, 24 mmol) was added. The reaction was refluxedovernight, then stopped and allowed to cool to roomtemperature. Water was added to the reaction mixture and agreen powder was filtered off. The resulting powder wasdissolved in chloroform and washed with 1 M HCl solution(3) and water (2). The resulting organic layer was driedover anhydrous sodium sulfate for 1 h (yield 68%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: H2TPP was prepared according to the following procedures[36, 37]. Co(TPP), MnIII(TPP)Cl and CoIII(TPP)Cl weresynthesized and purified by referring to the following procedures[36]. H2TPP was dissolved in DMF and the solutionwas heated to reflux with stirring. Then, cobalt acetate ormanganous acetate was added in three portions within30 min. When the thin-layer chromatography (silica) indicatedno free base porphyrin, the solution was cooled to70 C, and then 40 mL of 6 MHCl was added and stirred for4 h. The solution was cooled and the appeared solid wasfiltrated and washed with 3 M HCl until the filtrate no longerappeared red. The obtained solid was vacuum-dried, and itgave 85-98 % yield ofM(Cl)TPP (Co(Cl)TPP, Mn(Cl)TPP). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide;Reflux; | catalystsThe compound cobalt(II) meso-tetraphenyl porphyrin (CoTPP)was synthesized according to the literature [21]. Typically, distilledpyrrole (4.69 g, 70.0 mmol) was added dropwise into a three-neckflask containing a mixture of propanoic acid (250 mL), benzalde-hyde (5.56 g, 52.5 mmol) and 4-carboxy benzaldehyde (2.62 g,17.5 mmol), and then heated to reflux for 1 h. The obtained productwas cooled overnight, then filtered and purified. meso-Tetraphenylporphyrin was obtained. 1.0 g (1.6 mmol) of the as-synthesizedsample was dissolved in 100 mL N,N-dimethylformamide (DMF).After loading 2.5 g (10.5 mmol) of CoCl2·6H2O in batches, themixture was heated to reflux under stirring until meso-triphenylporphyrin was exhausted. Cooling overnight, the achieved mixturewas filtered and washed repeatedly with deionized water, and theproduct cobalt(II) meso-tetraphenyl porphyrin, denoted as CoTPP,was yielded. CoTPP was loaded in a quartz boat and pyrolyzedat different temperatures (namely, 600C, 700C and 800C) innitrogen atmosphere with the heating rate of 10C/min. The result-ing cobalt-nitrogen doped carbons were denoted as Co-N-C-600,Co-N-C-700 and Co-N-C-800. N-C-800 and CoOx-800, derivedfrom meso-tetraphenyl porphyrin and CoCl2·6H2O, respectively,were prepared for comparison. Co/N-C-800, prepared by imprega-nation method and Co-N-C/SiO2-800, with silica as support, weresynthesized for comparison as well. | |
In N,N-dimethyl-formamide;Reflux; | Cobalt tetraphenyl porphyrin was synthesized as the litera-ture reported previously [42]. During a typical synthesis process,0.1 mol benzaldehyde was added into a three-neck flask contain-ing 250 mL propanoic acid. Then the mixture was heated to thetarget temperature (130C) slowly and 0.1 mol freshly distilledpyrrole was added dropwise. After stirring for another 1 h, theobtained product was refrigerated overnight, then filtered and puri-fied. 1.6 mmol pure trtraphenyl porphyrin was transferred into100 mL N,N-dimethylformamide (DMF) solution, heating to refluxsubsequently. 0.01 mol cobalt chloride hexahydrate was added to the mixture in batches and kept for 1 h. After refrigerated overnight,the resulting product was filtered and washed with deionized waterfor several times. The end product was obtained and denoted asCoTPP after drying. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; for 12h;Reflux; | General procedure: Metalloporphyrins were prepared by refluxing porphyrins (0.33 mmol) with FeCl3, CoCl2, MnCl2, CuCl2, or Zn(OAc)2 (1.82 mmol) in N,N'-dimethylformamide (DMF, 70 mL) for 12 h. DMF was removed by distillation and the metalloporphyrins were precipitated by adding water. The precipitate was dissolved in 0.1 M NaOH solution and recrystallized by adding 1 M HCl solution. Finally, metalloporphyrins were filtered and dried under vacuum. | |
In N,N-dimethyl-formamide; at 89.84℃;Kinetics; Thermodynamic data; | General procedure: Porphyrins 1-6 (Aldrich, 97%), organic solvents (Merck, 99%), and inorganic salts (Acros, 99%) were used as received. The complex formation was studied by recording electronic absorption spectra of the solutions using a Cary 300 spectrophotometer (Varian). To do so,solutions of the studied porphyrin (2.5×10-5 mol/L)and the salt (2.5×10-3 mol/L) in an organic solvent were put in the cell maintained at constant temperature(±0.1C), and the absorbance at the wave length corresponding to the maximum in the spectrum of the formed metal porphyrinate was monitored. Kinetic studies of the complex formation were performed over 288-363 K range. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; for 12h;Reflux; | General procedure: Metalloporphyrins were prepared by refluxing porphyrins (0.33 mmol) with FeCl3, CoCl2, MnCl2, CuCl2, or Zn(OAc)2 (1.82 mmol) in N,N'-dimethylformamide (DMF, 70 mL) for 12 h. DMF was removed by distillation and the metalloporphyrins were precipitated by adding water. The precipitate was dissolved in 0.1 M NaOH solution and recrystallized by adding 1 M HCl solution. Finally, metalloporphyrins were filtered and dried under vacuum. | |
In N,N-dimethyl-formamide; at 24.84℃;Kinetics; Thermodynamic data; | General procedure: Porphyrins 1-6 (Aldrich, 97%), organic solvents (Merck, 99%), and inorganic salts (Acros, 99%) were used as received. The complex formation was studied by recording electronic absorption spectra of the solutions using a Cary 300 spectrophotometer (Varian). To do so,solutions of the studied porphyrin (2.5×10-5 mol/L)and the salt (2.5×10-3 mol/L) in an organic solvent were put in the cell maintained at constant temperature(±0.1C), and the absorbance at the wave length corresponding to the maximum in the spectrum of the formed metal porphyrinate was monitored. Kinetic studies of the complex formation were performed over 288-363 K range. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; at 350℃; for 0.0666667h;Inert atmosphere; Sealed tube; | Using a 50 mL volumetric flask, 1.208 g of copper sulfate as a metal salt was dissolved in 50 mL of distilled water to prepare a 0.1 mol / L CuSO 4 aqueous solution. Next, 0.02 g (3.3 × 10 -5 mol) of tetraphenylporphyrin (TPP) as a compound having a porphyrin-type skeleton, 0.02 g (3.3 × 10 -5 mol) of copper sulfate Aqueous solution of sodium carbonate and 0.032 g of sodium carbonate equivalent to copper sulfate to prevent corrosion of the reaction vessel, and the interior of the reaction vessel was purged with argon and sealed. Next, the reaction vessel was charged into the sand bath set at 350 C. The reaction temperature in the reaction vessel reached the reaction temperature in about 4 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.1%; 0.9%; 0.3%; 1.1%; 2.5%; 1% | With propionic acid; for 1h;Reflux; | Precursor porphyrins 12a-16a were all synthesized by a single procedure, where pyrrole (0.6 mL, 180 mmol) was added dropwise to a mixture containing benzaldehyde (0.23 mL, 45 mmol), 4-pyridinecarboxaldehyde (0.64 mL, 135 mmol) and propionic acid (25 mL). The resulting light yellow solution was placed under reflux for 1 h, turning into a dark colored mixture. Reaction mixture was then cooled to room temperature and added of 10 mL of acetone to give a precipitated that was collected by filtration and washed with acetone. The precipitate corresponded to a mixture of porphyrin 1 (TPP) and pyridyl porphyrins 12a-16a. The porphyrin mixture was then chromatographed onto a silica gel column that was eluted with chloroform, giving separately compounds 1, 12a and 13a with 0.3%, 0.9% and 1.1% yield, respectively. Column was then washed with methanol and the washes were concentrated to give a residue that corresponded to a mixture of porphyrins 14a-16a. A second silica gel column of the residue, eluted with chloroform:methanol (98:2) allowed the isolation of compounds 14a (1.0%), 15a (3.1%) and 16a (2.5%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In methanol; chloroform; at 20.0℃; | General procedure: 0.2 mmol of the corresponding 5,10,15,20-tetrakis(4-R-phenyl) porphyrin was dissolved in 40 ml of chloroform, to which a saturatedsolution of copper acetate in methanol was added. Themixture was magnetically stirred at room temperature, and theprogress of the reaction was monitored by TLC. The reaction isessentially complete in 2e3 h, and then distilled water (15 ml) isadded to wash the organic layer for 3 times. the organic layer wasdried over anhydrous MgSO4, and filtered. The solvent wasremoved by rotary evaporation yielding a purple powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With acetic acid; In toluene; at 120℃; for 0.583333h; | 5-Chloro-2,3,3-trimethylhydrazine 0.23 g (0.12 mmol) and 5,10,15,20-tetraphenyl-N-hybrid porphyrin 0.61 g (0.10 mmol) were dissolved in toluene Then, 1.2 mg (0.02 mmol) of glacial acetic acid was added, stirred for 5 minutes, and refluxed at 120 C for 0.5 hour. After the reaction was completed, the mixture was spin-dried and purified by filtration to give a purple compound, yield 94%. It is indicated that the desired photodynamic therapeutic agent can be synthesized in one step, and the obtained N-promiscuous porphyrin conjugated system can achieve near-infrared absorption, and the singlet oxygen yield is as high as 0.8-0.9, which solves the synthesis and light of the therapeutic agent. The problem of low absorption range and singlet oxygen yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In N,N-dimethyl-formamide; at 150.0℃; for 1h; | Meso-tetraphenylporphyrin 1 (0.5 g, 0.813 mmol) was dissolved in 80 mL DMF solution of MnCl2. 6H2O (1.9 g, 8.13 mmol) and refluxed at 150 0C for 1 h. The solvent mixture was removed from the crude product by distillation. It was later dissolved in 50 mL CH2Cl2, washed with distilled water (50 x 3) and dried over anhydrous Na2SO4. The product was purified by column chromatography using Al2O3 with CH2Cl2/methanol (95:5 V: V) as the eluent and dried under vacuum for 2-3 h. The yield found was 70 % (0.40 g). |
Tags: 917-23-7 synthesis path| 917-23-7 SDS| 917-23-7 COA| 917-23-7 purity| 917-23-7 application| 917-23-7 NMR| 917-23-7 COA| 917-23-7 structure
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Code | Phrase |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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