Name: 29162-73-0|Meso-tetra (p-bromophenyl) porphine|95%
Brand: Ambeed
SKU: A986218
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[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With propionic acid In dichloromethane for 0.333333h; Sealed tube; Microwave irradiation; Inert atmosphere; Schlenk technique;	2.2.2. Synthesis via microwave assisted method A vial was charged with 0.7 mL (10 mmol) of freshly distilled 1H-Pyrrole,1.85 g (10 mmol) of 4-bromobenzaldehyde, 10 mL ofCH2Cl2, and the appropriate volume of propionic acid of each entrydepicted in Table 1. The vial was capped with Teflon, deposited in aMicrowave reactor for 2 min at 300W, cooled and gently stirred atroom temperature for 5 min, and put back in the Microwavereactor. This procedure was repeated ten times for each trial,affording a black oil in each case. The crude products were purifiedusing the same chromatographic method described in the previoussection. The obtained yields are listed in Table 1, and the isolatedpurple solids were authenticated by 1H NMR, Mass spectrometryand Thin layer chromatography on silica gel (Rf 0.95, CHCl3:petroleumether 8:2 mixture (v:v)).
64.4%	With glacial acetic acid; propionic acid at 130℃; for 0.75h;	The first step is the synthesis of bromoporphyrins. Using 150 ml of a mixed acid of propionic acid/acetic acid (3:2, V/V) as a reaction solvent, and heating to reflux to 130 ° C, 10 g of bromobenzaldehyde (ie 0.055 mol) was dissolved in the reaction solvent under vigorous stirring, and 4.0 ml of freshly steamed pyrrole (ie 0.060 mol, 1.1 equivalent) was added dropwise within 2 min. The mixture was refluxed for 45 min, distilled off under reduced pressure to remove about 120 ml of mixed acid, cooled to minus 10 °C, and a purple solid was precipitated, suction filtered, and washed with methanol until the solid appeared to be bright purple. The methylene chloride and methanol systems were recrystallized in portions to give a purple solid 5,10,15,20-tetrakis(4-bromophenyl)porphyrin 8.1 g, yield 64.4%.
58%	Stage #1: pyrrole; 4-bromo-benzaldehyde With boron trifluoride diethyl ether complex In chloroform for 1h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform for 1h; Further stages.;

51.2%	Stage #1: pyrrole; 4-bromo-benzaldehyde With propionic acid In cyclohexane at 158.2℃; for 0.1h; Stage #2: In cyclohexane for 0.75h; Reflux;	15.1-15.4 Example 1 General procedure: (1) Prepare 560mol of pyrrole and 560mol of benzaldehyde into a mixed solution and set aside;(2) In a 2000L high-pressure titanium polymerization reactor 1 with a mechanical stirring and electric heating jacket and a distillation device on the top, add a solvent E consisting of 840L of propionic acid and 560L of cyclohexane,From the bottom of the polymerization reactor 1, N2 is bubbled to the oxygen concentration in the gas phase of the reactor top condenser outlet to be lower than 1%, and then the electrical heating jacket switch of the polymerization reactor 1 is started to heat the liquid in the polymerization reactor 1 to reflux. , Maintaining the pressure of the polymerization reactor 1 at 5.0atm, while adding the mixed solution prepared in step (1) from the top of the polymerization reactor 1 by dropwise addition, the molar concentration of pyrrole in the reaction solution is always kept lower than 0.1mol during the dropwise addition / L.The water produced by the reaction is removed from the system through a distillation device at the top of the polymerization reactor, and after condensing, it is delaminated by a liquid-liquid layering device 8 to circulate the upper oil phase back into the reaction system. The reflux ratio of the distillation column was continuously adjusted so that the water concentration in the polymerization reactor 1 was always lower than 0.05%. After the dropwise addition, the reaction was continued at the same time, and the reaction was stopped after 15 minutes. At the end of the reaction, the reaction temperature was 157.1 ° C. Then slowly cool it down. When the temperature in the polymerization reactor 1 drops to normal temperature, the reactants in the polymerization reactor 1 are filtered through the filtering and washing device 2 to obtain a filtrate and a crude TPP filter cake. The mass of the crude TPP filter cake is 54.8 kg. According to gas chromatography analysis, the amount of pyrrole remaining in the polymerization reaction system was 55.2 mol. The filtrate can be distilled into the polymerization solvent recovery tank 3 for distillation, and the solvent and unreacted pyrrole can be recovered. The recovered solvent and pyrrole are collected for recycling to the polymerization reactor 1 and continued to be used. The residue of the distillation kettle is discharged outside the system. deal with.(3) Add 54.8 kg of crude TPP filter cake obtained by centrifugal filtration to a 2000L oxidation reactor 4 with mechanical stirring and electric heating jacket, with condensation reflux at the top and gas distributor at the bottom, and simultaneously add 1400 kg of propylene into the kettle Acid, and simultaneously introducing nitrogen gas to replace the gas phase space in the oxidation reactor 4 to a tail oxygen concentration of less than 3%. Then, the switch of the electric heating jacket is started to heat the liquid in the oxidation reactor 4. When the liquid in the oxidation reactor 4 is heated to reflux, air is passed through to carry out the oxidation reaction. The oxidation reaction time is 22 minutes. During the reaction, the oxygen concentration in the tail gas is strictly controlled by adjusting the amount of the air to be passed to less than 3%. After the oxidation reaction was completed, it was left to cool slowly. When the temperature of the liquid in the oxidation reactor 4 is reduced to normal temperature, it is put into a filtering and washing device 5 for filtration to obtain a filtrate and a solid. The filtrate is dehydrated through an oxidation reaction solvent recovery tower 6 and dehydrated and recovered to obtain propionic acid, and the recovered propionic acid is collected. After that, it is ready to be used in the recycle and oxidation reactor 4 and the residue of the tower kettle is discharged out of the system. The filtrate can also be directly recycled to the oxidation reactor 4 without any treatment and continued to be used. The solid obtained by filtration was repeatedly washed with hot water and then filtered until the filtrate was colorless. Then repeatedly wash with methanol and then filter until the filtered wastewater is freecolor. The solid washed with methanol is the product TPP, and 46.0 kg of a tetraphenylporphine product is obtained after drying in a drying device 7 under vacuum at 80 ° C.The yield of the product TPP based on the pyrrole of the reactant was 59.3%, and the purity was 99.2%.
45%	With titanium(IV) tetrachloride In dichloromethane for 1h; Ambient temperature; other reagents: VOCl₃, VO(OEt)Cl₂, VO(OiPr)Cl₂, Mn(OAc)3;
43.3%	Stage #1: pyrrole; 4-bromo-benzaldehyde In cyclohexane; propionic acid at 158.2℃; for 0.466667h; Large scale; Green chemistry; Stage #2: With air In cyclohexane; propionic acid for 0.9h; Large scale; Green chemistry;	19 (1) 560 mol of pyrrole and 560 mol of benzaldehyde were mixed to prepare a mixed solution, alternate;(2) In a 2000L titanium high pressure polymerization reactor 1 with mechanically stirred and electrically heated jacket with distillation device on top, solvent E consisting of 840L propionic acid and 560L cyclohexane was added, and the concentration of oxygen in the gas phase from the bottom of the polymerization reactor 1 where N2 is bubbled into the top of the reactor condenser was less than 1%,then, the polymerization reactor 1 was started to heat the jacket switch, the liquid in the polymerization reactor 1 was heated to reflux, maintaining the polymerization reactor 1 pressure 5.0 atm, at the same time, the mixed solution prepared in step (1) was added dropwise from the top of the polymerization reactor 1 in a dropwise manner, and the molar concentration of pyrrole in the reaction liquid was maintained at less than 0.1 mol/L during the dropwise addition. The water produced by the reaction was removed from the system through the distillation device at the top of the polymerization reactor 1, condensed, and then separated by the liquid-liquid layering device 4, and the upper oil phase was recycled back to the reaction system. The reflux ratio of the distillation column was constantly adjusted so that the water concentration in the polymerization reactor 1 was always lower than 0.05%.After the addition, the reaction was continued at the same time, and the reaction was stopped after 15 minutes. At the end of the reaction, the reaction temperature was 157.1°C. At this point, the polymerization reactor 1 is maintained at a pressure of 5 atm, air was passed into the oxidation reaction, oxidation reaction time was 22 minutes, during the reaction, the oxygen concentration in the exhaust gas was strictly controlled to be less than 2% by adjusting the amount of passed air. After completion of the oxidation reaction, left to cool slowly. When the temperature of the liquid in the polymerization reactor 1 drops to room temperature, it was filtered through the filter washing device 2 to obtain the filtrate and filter cake, and the filtrate was subjected to rectification and dehydration in the solvent recovery column 3 of the polymerization reaction to recover the solvent,the recovered solvent is collected to be recycled back to the system for continued use, and the residue of the tower reactor is discharged out of the system. The filtered cake was repeatedly washed with hot water and filtered until the filtrate was colorless. The filter cake was then washed repeatedly with methanol and filtered until the filtered waste water was colorless. The filter cake washed with methanol was the product TPP, after vacuum drying at 80°C51.4of 98.7%. The process flow is the same as that of embodiment 9, the difference being: (1) Add 672 moles of pyrrole and 1067 moles of bromobenzaldehyde; (2) The reaction time in the polymerization reactor is 28 minutes and the reaction pressure is 5 atm. At the end of the reaction, the reaction temperature was 158.2°C. The concentration of water in the polymerization reactor is controlled to be always lower than 0.04%; (3) The gas introduced into the oxidation reactor is air and the reaction time is 54 minutes; According to this method, the final solid obtained after vacuum drying at 80 ° C to obtain product TPP67.7kg. The product TPP had a synthetic yield of 43.3% and a purity of 99.2% based on the reactant pyridine.
42%	Stage #1: pyrrole; 4-bromo-benzaldehyde With boron trifluoride diethyl ether complex In chloroform at 20℃; for 1h; Inert atmosphere; Stage #2: With triethylamine In chloroform at 90℃; for 1h; Inert atmosphere;
42%	at 120℃; for 1h;
41%	With propionic acid for 0.5h; Reflux;	2.1.3. Synthetic procedure used for preparation of H2TXPP General procedure: Adler method has been employed using direct condensation reactionof equimolar amounts of freshly distilled pyrrole (20 mmol) and4-halobenzaldehyde; halo = fluoro, chloro, bromo and iodo(20 mmol) added to propionic acid (20 ml) and heated to a refluxingtemperature. The solutions were allowed to reflux and put on constantstirring for about 30 min. The reaction mixture was allowed to cool atroom temperature (30 °C). Later reaction mixtures were filtered andthe residues were washed with methanol until the filtrate wascolourless. The courses of reaction were monitored and purity of thesecorresponding compounds has been achieved by column chromatographyon a basic alumina. However CHCl3was used as eluent in all cases.Compounds were re-crystallized from CHCl3 on vacuum further subjectedto various spectroscopic studies.
36%	With propionic acid In nitrobenzene at 200℃; for 0.25h; Sealed tube; Microwave irradiation;
35%	With trifluoroacetic acid In para-xylene for 1h; Dean-Stark; Reflux;	2.2.1. Synthesis of 5,10,15,20-tetrakis(4'-bromophenyl)porphin 2.0 mL of trifluoroacetic acid and 150.0 mL of para -xylene were placed into a 1 L three-neck flask equipped with a Dean-Stark trap, a reflux condenser, an air feed pipe, and a dropping funnel. The mixture was heated to the para -xylene boiling point and a solution of 13.3 g (72 mmol) of 4-bromobenzaldehyde and 5 g (72 mmol) of pyrrole was added from the dropping funnel to 150 mL of para - xylene, with air simultaneously passed through the mixture. The reaction mixture was boiled for 1 hour, with air simulta- neously passed through it. Then the mixture was cooled to room temperature, 2 mL of diethanolamine were added, and after that, the mixture was left overnight. Then the porphyrin precipitate was filtered, washed with ethanol, and dried at room tempera- ture until its weight became constant. For purification, the por- phyrin was dissolved in dichloromethane and chromatographed on aluminum oxide, Brockman activity grade II, with simultaneous dichloromethane elution. The porphyrin eluate was evaporated and precipitated with ethanol. Yield: 5.9 g (35%). 1 H NMR (CDCl 3 , 500 MHz): -2.85 (bs, 2H, NH), 7.92 (d, 8H, J = 8.0 Hz, Ar), 8.10 (d, 8H, J = 8.0 Hz, Ar), 8.87 (s, 8H, H-pyrrole). Elemental analysis: calculated:% H 2.820; C 56.810; N 6.02; Br 34.35; determined experimentally:%H 2468; C 56,595; N 5632; Br 34,35. UV-vis: max , nm (lg ): 650(3.95), 590(3.89), 549(4.04), 515(4.34), 419(5.68) (CHCl 3 ). MALDI-TOF MS: m/z calculated: C 44 H 26 Br 4 N 4 , 929.8911; deter- mined experimentally: 929.6612 [M] + .
34%	Stage #1: pyrrole; 4-bromo-benzaldehyde With trifluoroacetic acid In dichloromethane for 3.41667h; Inert atmosphere; Darkness; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 1h; Inert atmosphere;
34.2%	With propionic acid for 2h; Reflux;
34%	With glacial acetic acid In nitrobenzene at 120℃; for 1h;
33%	With glacial acetic acid In nitrobenzene at 120℃; for 1h;
32%	With glacial acetic acid; nitrobenzene at 120℃; for 1h;
31%
30%	With propionic acid; nitrobenzene at 200℃; for 0.0833333h; Microwave irradiation; Sealed vessel;
30%	With glacial acetic acid In nitrobenzene at 120℃; for 1h;
30%	With propionic acid at 140℃; for 12h; Inert atmosphere;	1 2.5. Synthesis of tetra and octabromo porphyrins 12 and 13 General procedure: A mixture of p-bromobenzaldehyde or 3,5-dibromobenzaldehyde(21.74 mmol), propionic acid 25 mL and (21.74 mmol) ofpyrrole, the mixture was heated at 140 °C and stirred vigorouslyunder nitrogen atmosphere for 12 h. after that, water was addedand precipitated was formed, the mixture wasfiltered and the solidwas washed with hot water and methanol obtaining a purple solid.2.5.1. 5,10,15,50-(Tetra-p-bromophenyl) porphyrin 12Yield 30%. UV-vis (CHCl3 nm); 660, 616, 450, 420, 370, 290. IR(KBr cm-1); 3313, 1556, 1469, 1388, 1345, 1245, 1214, 1179, 1096,1066, 1009, 985, 961, 873, 841, 749, 731, 709, 638, 553, 520, 449. 1HNMR (300 MHz, CDCl3) δ(ppm):2.85 (br, 2H, NH), 7.90 (d, 8H,J = 8.4 Hz, Ar), 8.06 (d, 8H, J = 8.1 Hz, Ar), 8.84 (s, 8H, Py). 13C NMR(75 MHz, CDCl3) δ (ppm); 118.9 (Ar), 122.6 (Ar), 129.9 (b-Py), 131.3(Ar), 135.8 (Aripso), 140.8 (Ar-Br). FAB m/z: 930.0. Anal. Elem. calc.for: C44H26Br4N4, C, 56.80; H, 2.82; Br, 34.36; N, 6.0 2%. Found: C,56.82; H, 2.83; N, 6.02%.
30.4%	In propionic acid for 2h; Reflux;
29%	With glacial acetic acid In nitrobenzene at 120℃; for 1h;
26%	Stage #1: 4-bromo-benzaldehyde With benzoic acid at 200℃; for 0.0833333h; Stage #2: pyrrole at 200℃; for 0.333333h;
25%	In glacial acetic acid; nitrobenzene at 120℃;
25%	In propionic acid at 141℃; for 1h; Reflux;	meso-tetrakis(4-bromophenyl)porphyrin (Br₄TPPH2) 3.5 mL (0.05 mol)pyrrole and 9 g (0.05 mol)4-bromobenzaldehydewere added to 200 mL of refluxing propionic acid. After refluxing at 141 oC for 1h, the reaction mixture was cooled to room temperature. Thereaction was monitored by TLC with DCM as eluent. After filtration the filtercake was washed with methanol and hot water and purified by columnchromatography on silica gel eluting by n-Hexane/DCM 2:1 follow by n-Hexane/DCM1:1 system. Yield 25 %. FT-IR n (cm-1):3320 (NH), 3022-3058 (CH Ar), 1472 (C=N),1348-1390 (=C-N), 1011 (C-Hpyrrole), 964(C-Hporp. ring) , 782(C-H pyr. ring), 724 (NH bending).1H NMR (CDCl3), δ (ppm)=-2.94 (s, 2H, NH),7.83 (d, 8H, CHAr-phenyl),7.98 (d, 8H, CHAr-phenyl), 8.76 (s, 8H, CHpyrrole).13C NMR (CDCl3),δ (ppm)= 117.98(Cmeso),121.61(CH-C3), 128.96 (CH-Cβ), 134.79 (CH-C2),139.80 (C1). UV-visible (CHCl3),λmax(nm) = 418; 512; 547;588; 644. Mass (ESI-MS, m/z): C44H26N4Br4([M+H]+), calcd: 930.3200, found: 930.6624
25%	With propionic acid for 0.5h; Reflux;
25%	With propionic acid at 141℃; for 1h;
24%	With propionic acid for 3h; Reflux;
23%	Stage #1: pyrrole; 4-bromo-benzaldehyde With iodine In dichloromethane at 40℃; for 0.0833333h; Microwave irradiation; Stage #2: With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione In dichloromethane at 40℃; for 0.0166667h; Microwave irradiation;
22.6%	In propionic acid at 140℃;
22%	Stage #1: pyrrole; 4-bromo-benzaldehyde In dichloromethane for 1h; Inert atmosphere; Stage #2: With trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 1h; Inert atmosphere;
22%	Stage #1: 4-bromo-benzaldehyde With propionic acid; propionic acid anhydride at 20℃; for 0.75h; Inert atmosphere; Stage #2: pyrrole at 150℃; for 4h; Inert atmosphere;	1.1-1.3; 2.1-2.3; 3.1-3.3; 4.1-4.3 Example 4 5g of p-bromobenzaldehyde was dissolved in 300mL of propionic acid at room temperature,In the propionic anhydride mixed solvent (the molar ratio of propionic acid and propionic anhydride is 2.5:1),Stirring to accelerate the dissolution in nitrogen atmosphere for 45min, after complete dissolution.2) Take the solution in step 1) and transfer it to a 150°C oil bath, preheat for a period of time and stir while slowly adding a mixed solution of 10mL propionic acid and 2.05g pyrrole dropwise, adding a condenser tube after the dropwise addition,The reaction was continued for 4 h at 150°C.3) get the solution that the reaction is completed in step 2) and add pure water to carry out precipitation, then filter the obtained product to remove the precipitation and wash to remove the solvent completely, and then purify,The dark purple powder obtained by drying is porphyrin crystal BrTPP (yield: 22%).
21.5%	In propionic acid for 12h; Reflux;
21%	With glacial acetic acid In nitrobenzene at 120℃; for 1h;
20%	With propionic acid at 150℃; for 1h;
20%	With propionic acid for 0.5h; Reflux;	1 Synthesis of Tetra(4-Aminophenyl) Copper Porphyrin Weigh 7.40g (0.04mol) of p-bromobenzaldehyde, dissolve it in 30ml propionic acid, add it dropwise to the refluxing 100ml propionic acid at the same time as 20ml propionic acid solution containing 2.80ml pyrrole (0.04mol), continue after the addition is complete Reflux for 30min, After cooling to room temperature, put it in the refrigerator and let it stand overnight, filter with suction, wash the filter cake with methanol, and then wash with water. It was washed with methanol and dried under vacuum to obtain tetrakis(4-bromophenyl)porphyrin, 1.86 g, with a yield of 20%.
19%	With air; 2-chloroacetic acid In xylene for 1.5h; Heating;
19.7%	With propionic acid In acetic anhydride; dimethyl sulfoxide for 2h; Inert atmosphere; Reflux;
19.5%	Stage #1: pyrrole; 4-bromo-benzaldehyde With trifluoroacetic acid In dichloromethane at 25℃; for 1h; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 1h;	2 In the 25 °C, N2Under the protection of the 800 ml dry dichloromethane, 3.7g 4 - bromophenylacetic formaldehyde (20mmol), 1.4 ml pyrrole (20mmol) adding 1000 ml round bottom three flasks, stirring until the solid completely dissolved, is added 3.7 ml trifluoroacetic acid (50mmol, 2 . 5eq) stirring 1h, then adding 9.08g DDQ (2.3 - dichloro - 5, 6 - dicyano - 1, 4 - benzoquinone) stirring 1h. The above-mentioned liquid pressure reducing filter, reduced pressure distillation to remove the solvent, the obtained crude product via a chromatographic column separation [fixed phase: aluminum oxide; mobile phase: dichloromethane/petroleum ether (volume ratio)=2:1], to obtain four (4 - bromophenyl) porphyrin, the conversion of the product 19.5%.
19.5%	Stage #1: pyrrole; 4-bromo-benzaldehyde With trifluoroacetic acid In dichloromethane at 25℃; for 1h; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 1h;	6 In the 25 °C, N2Under the protection of the 800 ml dry dichloromethane, 3.7g 4 - bromophenylacetic formaldehyde (20mmol), 1.4 ml pyrrole (20mmol) adding 1000 ml round bottom three flasks, stirring until the solid completely dissolved, is added 3.7 ml trifluoroacetic acid (50mmol, 2 . 5eq) stirring 1h, then adding 9.08g DDQ (2.3 - dichloro - 5, 6 - dicyano - 1, 4 - benzoquinone) stirring 1h, will be the above-mentioned liquid and vacuum filtration, vacuum distillation to remove the solvent, the resulting crude product via a chromatographic column separation [fixed phase: aluminum oxide; mobile phase: dichloromethane/petroleum ether (volume ratio)=2:1], to obtain four (4 - bromophenyl) porphyrin, the conversion of the product 19.5%.
19%	With propionic acid at 120℃; for 1h;
15%	Stage #1: 4-bromo-benzaldehyde With glacial acetic acid Reflux; Stage #2: pyrrole for 0.5h; Reflux;	Meso-tetrakis(4-bromophenyl)porphyrin (H2TBrPP) 4-Bromobenzaldehyde(7 g, 37.8 mmol) was dissolved in acetic acid (150 mL) andthe solution was heated under reflux conditions. Pyrrole (2.6 mL, 37.8mmol) was added drop-wise and the dark mixture was heated for afurther 30 min. After cooling, the black tarry mixture was filtered toobtain a purple solid which, after washing with methanol and water,lead to the porphyrin derivative as purple crystals (15%). 1H NMR[CDCl3, 400 MHz]: δ (ppm) 2.86 (s, 2H, NHpyrro), 7.88 (d, 8H, 3JHoHm= 8.1 Hz, Hm-Hm’), 8.02 (d, 8H, 3JHoHm = 8.1 Hz, Ho-Ho’), 8.80 (s, 8H,Hβ). UV-vis (in CH2Cl2) [λmax, nm, (ε, M 1 cm 1)] 419 (4.52 × 106), 515(2.05 × 105), 549 (8.51 × 104), 590 (5.88 × 104), 648 (4.78 × 104). MS[ESI]: m/z calcd for C44H26Br4N4: 930.32, found: 930.38. FTIR cm 1:3317 ν(NH porphyrin), 2926 and 2845 ν(CH porphyrin), 966 (δCCHporphyrin), 731 ν(C-Br porphyrin). Anal. Calcd. for C44H26Br4N4: C,56.8; H, 2.81; N, 6.02. Found: C, 56.5; H, 2.79; N, 6.08.
12%	Stage #1: pyrrole; 4-bromo-benzaldehyde With boron trifluoride diethyl ether complex In dichloromethane at 20℃; for 2h; Stage #2: With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione In dichloromethane for 2h; Heating;
12%	In propionic acid at 125 - 130℃; for 3h;	1. Synthesis of meso-tetra (4-bromophenyl)porphyrin (PP1) The synthesis was carried out according to literature methods with slight modifications as follows:Freshly distilled pyrrole (1.20 mL, 18 mmol) was added dropwise to a warm solution of 4-bromobenzaldehyde (3.24 g, 18 mmol) in propionic acid (80 mL). The mixture was brought toreflux temperature (125-130°C) with stirring for 3 h. The progress of the reaction was continuallymonitored by TLC and UV-visible absorption spectroscopy. The reaction vessel was allowed tocool to room temperature and 50 mL methanol was added to further quench the solution and aidcrystallization. The product was collected as a purple solid by vacuum filtration, washed withmethanol and left to dry in open air. The product was further purified by elution in a column ofsilica gel with ethyl acetate: hexane (1:9 v/v) mobile phase.Yield: Purple solid 2.01 g (12%). UV-vis (Toluene) λmax nm (ε (L Mol-1 cm-1)): 421 (2.1 × 105),517 (9.4 × 103), 550 (4.5 × 103), 593 (2.7 × 103) and 650 (2.1 × 103). 1H NMR (400 MHz, CDCl3)δH ppm 8.84 (s, 8H, β Pyrrol), 8.06 (d, J= 8.3 Hz, 8H), 7.90 (d, J= 8.3 Hz, 8H). IR νmax cm-1 3320(N-H), 3000 (=C-Hstr), 1370 (C-Nstr). Calc. for C44H26Br4N4: C = 56.81, H = 3.03, N = 6.01; foundC = 56.54, H = 3.00, N = 6.10. MALDI-TOF-MS m/z: calcd = 930.34, found = 930.94 [M+].
11%	In lithium hydroxide monohydrate at 199.84℃; for 0.166667h; Microwave irradiation; Green chemistry;
	With propionic acid for 30h; Heating;
	With trifluoroacetic acid In dichloromethane; lithium hydroxide monohydrate for 2h;
	In propionic acid at 120℃; for 1.5h;
	Stage #1: pyrrole; 4-bromo-benzaldehyde With trifluoroacetic acid In dichloromethane for 1h; Darkness; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 1h; Inert atmosphere;
	Stage #1: pyrrole; 4-bromo-benzaldehyde In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: With boron trifluoride diethyl ether complex In dichloromethane for 2h; Stage #3: With 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione In 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran for 2h; Reflux;
	With propionic acid at 130℃; for 1h;
	With glacial acetic acid In nitrobenzene
	With propionic acid for 2h; Reflux;
	With propionic acid Reflux;	2.2.4. Preparation of different porphyrin ligands General procedure: Porphyrin ligands were synthesized by the method of Alder with some modifications [25]. In a 100 mL of flask with three necks,0.015 mol of corresponding benzaldehyde was dissolved in 30 mL of propionic acid solution. The mixture was heated at reflux temperature with vigorous stirring. Subsequently, 0.015 mol of freshly distilled pyrrole solved in propionic acid solution (5 mL) was slowly added intothe above mixture. After a period of time of reaction, the mixture solution was cooled to room temperature and placed in the refrigerator overnight. Then the purple solid was filtered and washed with hot water and ethanol and dried at 80 °C for 8 h. The crude product was purified via column chromatography using neutral alumina (100-200 mesh size) with chloroform or dichloromethane as eluent.
	With propionic acid Reflux;
	Stage #1: 4-bromo-benzaldehyde With propionic acid at 140℃; Inert atmosphere; Stage #2: pyrrole for 1.5h;	2 (2) Monomers of 5,10,15,20-tetra(4-bromophenyl)porphyrin (H2TBrPP) and 5,10,15,20-tetra(4-bromophenyl)iron porphyrin (FeTBrPP) Synthesis of synthetic monomer 5,10,15,20-tetra(4-bromophenyl)porphyrin (H2TBrPP) (i) Weigh p-bromobenzaldehyde (0.02mol, 3.7g) into a 250mL three-necked flask, then measure 80mL of propionic acid in a graduated cylinder and add it to the three-necked flask.(ii) Add magnets, set up a condensing reflux device, open the nitrogen valve, pass nitrogen, and react under a nitrogen atmosphere during the whole process. Turn on stirring and heating. The heating temperature is sufficient to make propionic acid reflux (temperature is about 140°C).(iii) Add 2mL of re-distilled pyrrole to 10mL of propionic acid, and add it dropwise (about 10min) with a dropping funnel. The system gradually turns black. After 0.5h, purple crystals appear on the wall of the flask, and then react for 1h.(iv) Stop heating and stirring, close the nitrogen valve, and after cooling to room temperature, add 80 mL of methanol and stir magnetically at room temperature for 1 hour.(v) Vacuum filtration under reduced pressure, rinse with 30 mL of deionized water (heated with water), and then rinse with a large amount of methanol until the rinsed droplets are colorless. A purple filter cake is obtained.(vi) Then take a small amount of purple filter cake and dissolve it in a 250 mL single-necked flask with a small amount of chloroform, but to ensure that all is dissolved, slowly add methanol and perform recrystallization twice. Bright purple crystal particles are obtained at the bottom of the flask,Monomer5,10,15,20-Tetra(4-bromophenyl)porphyrin(H2TBrPP).
	With propionic acid for 0.5h; Reflux;	Synthesis of monometallic cobalt porphyrin General procedure: 5,10,15,20-tetrakis(4-bromophenyl)-21H,23H-porphyrin (TBPP)was synthesized firstly. The typical procedure: 18.5 g (0.1 mol) of pbromobenzaldehydedissolved in 120 mL of propionic acid and heatedto reflux, within 30 min dropwise addition of 30 mL of propionic acidsolution dissolved in 6.7 g (0.1 mol) of pyrrole. After refluxing for 0.5 h,it was cooled to room temperature and filtered with suction to obtain asolid, which was washed three times with 50 mL of methanol. Recrystallizedthree times with chloroform: methanol (15 mL:60 mL) and driedto obtain 5,101,520-tetrakis(4-bromophenyl)-21H,23H-porphyrin(TBPP) purple crystals. The product was characterized by 1HMR,UV-vis and FT-IR, and proved to be TBPP.Then 0.93 g (1 mmol) and 2.85 g CoCl2• 6H2O (12 mmol) of the obtainedTBPP placed in a round bottom flask, add 100 mL of DMF, andheat to reflux for 12 h. After cooling to room temperature, the precipitatewas precipitated by adding water and suction filtered. Afterwashing with water and methanol several times, it was vacuum dried at70 C for 8 h to obtain a red-brown cobalt porphyrin complex Co(II)(5,10,15,20-tetrakis(4-bromophenyl)-21H,23H-porphyrin) (CoTBPP)

Reference： [1]Matamala-Cea, Edison; Valenzuela-Godoy, Fabián; González, Déborah; Arancibia, Rodrigo; Dorcet, Vincent; Hamon, Jean-René; Novoa, Néstor [Journal of Molecular Structure, 2020, vol. 1201]
[2]Current Patent Assignee: HUNAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN109705161, 2019, A Location in patent: Paragraph 0040; 0043
[3]Capitosti, Gregory J.; Guerrero, Carol D.; Binkley Jr., David E.; Rajesh, Cheruvallil S.; Modarelli, David A. [Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 247 - 261]
[4]Current Patent Assignee: TANG JIANGTAO - CN105198890, 2018, B Location in patent: Paragraph 0059-0062; 0103-0110; 0160-0166
[5]Gradillas, Ana; Campo, Carmen del; Sinisterra, Jose V.; Llama, Emilio F. [Journal of the Chemical Society. Perkin transactions I, 1995, # 20, p. 2611 - 2614]
[6]Current Patent Assignee: TANG JIANGTAO - CN105085536, 2018, B Location in patent: Paragraph 0060; 0171-0176
[7]Dechant, Moritz; Gerbig, Lisa; Ghosh, Tapas; Lambov, Martin; Lehmann, Matthias [Journal of Materials Chemistry C, 2020, vol. 8, # 16, p. 5562 - 5571]
[8]Han, Sheng; Ji, Huiping; Ke, Changchun; Lu, Chenbao; Wang, Tianfu; Xu, Qing; Yang, Shuai; Yuan, Yajie; Zhao, Yazhen; Zhu, Jinhui; Zhuang, Xiaodong [Chemical Communications, 2022, vol. 58, # 12, p. 1966 - 1969]
[9]Dar, Umar Ali; Shah, Shakeel A. [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 240]
[10]Ferrero, Sergio; Barbero, Héctor; Miguel, Daniel; García-Rodríguez, Raúl; Álvarez, Celedonio M. [RSC Advances, 2020, vol. 10, # 59, p. 36164 - 36173]
[11]Pukhovskaya; Ivanova; Kiselev; Fomina; Syrbu [Journal of Molecular Structure, 2021, vol. 1238]
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[13]Kurniawan, Fransiska; Miura, Youhei; Kartasasmita, Rahmana Emran; Mutalib, Abdul; Yoshioka, Naoki; Tjahjono, Daryono Hadi [Pharmaceuticals, 2018, vol. 11, # 1]
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[19]Liu, Xiaoming; Xu, Yanhong; Guo, Zhaoqi; Nagai, Atsushi; Jiang, Donglin [Chemical Communications, 2013, vol. 49, # 31, p. 3233 - 3235] Cui, Di; Yao, Chan; Xu, Yanhong [Chemical Communications, 2017, vol. 53, # 83, p. 11422 - 11425]
[20]Organista-Mateos, Ulises; Martínez-Klimov, Mark E.; Pedro-Hernández, Luis D.; Borja-Miranda, Andrés; Cortez-Maya, Sandra; Hernández-Ortega, Simón; Martínez-García, Marcos [Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 343, p. 58 - 65]
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[24]Pereira, Mariette M.; Muller, Guillermo; Ordinas, Juan Ignacio; Azenhaa, M. Emilia; Arnaut, Luis G. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 9, p. 1583 - 1588]
[25]Önal, Emel; Ahsen, Vefa; Pécaut, Jacques; Luneau, Dominique; Hirel, Catherine [Tetrahedron Letters, 2015, vol. 56, # 37, p. 5157 - 5160]
[26]Yaman, Hanifi; Kayan, Asgar [Journal of Porphyrins and Phthalocyanines, 2017, vol. 21, # 3, p. 231 - 237]
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[28]Harmandar, Kevser; Tunç, Gülenay; Küçük, Tuğba; Gürek, Ayşe Gül; Atilla, Devrim [Journal of Porphyrins and Phthalocyanines, 2022, vol. 26, # 1, p. 78 - 83]
[29]Hampel, Frank; Jux, Norbert; Martin, Max M.; Oleszak, Christoph [European Journal of Organic Chemistry, 2020, vol. 2020, # 43, p. 6758 - 6762]
[30]Location in patent: experimental part Liu, Yijiang; Guo, Xia; Xiang, Na; Zhao, Bin; Huang, Hui; Li, Hui; Shen, Ping; Tan, Songting [Journal of Materials Chemistry, 2010, vol. 20, # 6, p. 1140 - 1146]
[31]Sheng, Xingfeng; Guo, Hongchen; Qin, Yusheng; Wang, Xianhong; Wang, Fosong [RSC Advances, 2015, vol. 5, # 40, p. 31664 - 31669]
[32]Current Patent Assignee: UNIV HEFEI - CN114380839, 2022, A Location in patent: Paragraph 0034-0050
[33]Lv, Xiu-Liang; Wang, Kecheng; Wang, Bin; Su, Jie; Zou, Xiaodong; Xie, Yabo; Li, Jian-Rong; Zhou, Hong-Cai [Journal of the American Chemical Society, 2017, vol. 139, # 1, p. 211 - 217]
[34]Lv, Xuehui; Chen, Yanli; Wu, Yanling; Wang, Haoyuan; Wang, Xinlong; Wei, Chuangyu; Xiao, Zuoxu; Yang, Guangwu; Jiang, Jianzhuang [Journal of Materials Chemistry A, 2019, vol. 7, # 47, p. 27089 - 27098]
[35]Eder, Grace M.; Pyles, David A.; Wolfson, Eric R.; McGrier, Psaras L. [Chemical Communications, 2019, vol. 55, # 50, p. 7195 - 7198]
[36]Current Patent Assignee: CHEMICAL RES INSTITUTE ACADEMY OF MILITARY SCIENCE - CN112939992, 2021, A Location in patent: Paragraph 0044-0046
[37]Semeikin, A. S.; Koifman, O. I.; Berezin, B. D. [Chemistry of Heterocyclic Compounds, 1986, vol. 22, # 6, p. 629 - 632][Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 6, p. 798 - 801]
[38]Location in patent: experimental part Wang, Xiaochen; Wang, Haiqiao; Yang, Yi; He, Youjun; Zhang, Lei; Li, Yongfang; Li, Xiaoyu [Macromolecules, 2010, vol. 43, # 2, p. 709 - 715]
[39]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104327036, 2017, B Location in patent: Paragraph 0117
[40]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104327036, 2017, B Location in patent: Paragraph 0137
[41]Yuan, Kuo; Song, Tianqun; Wang, Dawei; Zhang, Xiaotao; Gao, Xiong; Zou, Ye; Dong, Huanli; Tang, Zhiyong; Hu, Wenping [Angewandte Chemie - International Edition, 2018, vol. 57, # 20, p. 5708 - 5713][Angew. Chem., 2018, vol. 130, p. 5810 - 5815,6]
[42]Amiri, Nesrine; Ben Taheur, Fadia; Chevreux, Sylviane; Dorcet, Vincent; Lemercier, Gilles; Nasri, Habib; Rodrigues, Carine Machado [Inorganica Chimica Acta, 2021, vol. 525]
[43]Nielsen, Christian B.; Krebs, Frederik C. [Tetrahedron Letters, 2005, vol. 46, # 35, p. 5935 - 5939]
[44]Amuhaya, Edith K.; Derese, Solomon; Lanterna, Anabel E.; Mack, John; Nyokong, Tebello; Otieno, Sebastian; Scaiano, Juan C. [Molecules, 2021, vol. 26, # 11]
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[56]Current Patent Assignee: SHANDONG UNIVERSITY - CN111559951, 2020, A Location in patent: Paragraph 0087-0093
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2
[ 22112-84-1 ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; sodium nitrite 1)5 deg C, 2)100 deg. C; Yield given. Multistep reaction;
	Stage #1: tetrakis(4-aminophenyl)porphyrin With hydrogenchloride; sodium nitrite In water for 0.166667h; Cooling with ice; Stage #2: With potassium bromide In water at 20℃; for 2.83333h; Cooling with ice;	1 Example 1 Commercially available tetrakis (4-aminophenyl) porphyrin (TATPP) (675 mg, 0 • 10 mmol)Dissolved in 33mL concentrated hydrochloric acid, Dropped in ice bath 5mL Sodium nitrite aqueous solution (NaNO2 concentration of 0.2mmol / mL), Reaction 10min; then 5mL was added dropwise potassium bromide aqueous solution (KBr concentration: 0.2 mmol / mL) Continue reaction 20min, Warmed to room temperature, Reaction 2.5h. The product was neutralized with ammonia to pH 8, Extracted with dichloromethane,The organic layer is washed with water until neutral,The methylene chloride was evaporated under reduced pressure, Drying in a vacuum oven for 2h.Crude product was separated by silica gel column, Dichloromethane as developing solvent, The first ribbon product was collected, 5,10,15,20-tetrabromophenyl porphyrin (TBrTPP) was obtained.

Reference： [1]Semeikin, A.S.; Koifman, O.I.; Berezin, B.D. [Chemistry of Heterocyclic Compounds, 1986, vol. 22, # 4, p. 397 - 401][Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 4, p. 486 - 490]
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY CITY COLLEGE - CN106317062, 2017, A Location in patent: Paragraph 0038; 0039

3
[ 29162-73-0 ]
[ 107099-99-0 ]
meso-Tetrakis<4-(2,5-dimethoxyphenyl)phenyl>porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In toluene at 90℃; for 48h;
74%	With potassium carbonate In ethanol; toluene for 48h; Heating;

Reference： [1]Chan, Chi-Shing; Tse, Andy K.-S.; Chan, Kin Shing [Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 6084 - 6089]
[2]Capitosti, Gregory J.; Guerrero, Carol D.; Binkley Jr., David E.; Rajesh, Cheruvallil S.; Modarelli, David A. [Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 247 - 261]

4
[ 29162-73-0 ]
[ 1066-54-2 ]
meso-tetrakis<4-<2-(trimethylsilyl)ethynyl>phenyl>porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine at 90℃; for 48h;

Reference： [1]Chan, Chi-Shing; Tse, Andy K.-S.; Chan, Kin Shing [Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 6084 - 6089]

5
5,10,15,20-tetrakis-(4-bromo-phenyl)-porphyrinogene [ No CAS ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; toluene
	With air In dichloromethane at 39℃; for 4h;
	With air In dichloromethane at 39℃;

	With air In dichloromethane at 39℃; for 3h;
135 mg	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 2h; Inert atmosphere; Darkness;
	With ammonium cerium (IV) nitrate In dichloromethane at 20℃; for 0.333333h; Green chemistry;	Synthesis of porphyrins 2a-j (General method). General procedure: Pyrrole (0.07 ml, 1 mmol), aldehyde (1 mmol), 50% nano-TiCl4·SiO2 (0.1 g), and CH2Cl2 (20 ml) were placed in a 50 ml beaker. The mixture was stirred at room temperature within the time specified in Table 2. The progress of the reaction was monitored by TLC. After the reaction was finished, CAN (0.1 g, 5 mol %) was added to the reaction mixture and stirred at room temperature for 20 min in the presence of air while the reaction mixture became dark-purple indicating porphyrinogen conversion into porphyrin under aerobic oxidation. The solution was concentrated under reduced pressure and chromatographed on neutral alumina column eluting with CH2Cl2-petroleum ether, 1:1.5. Alternatively, crude solid residues obtained by the evaporation of the corresponding reaction mixtures were sequentially washed with Et2O, hot H2O, and cold MeOH to give pure porphyrins as purple solid.
	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 0.0833333h; Inert atmosphere;	2.1 General procedure for the synthesis of A3-corrole (3a-f) General procedure: For the synthesis of corrole, a round-bottom flask with N2saturated dichloromethane (10 mL) was used in which substituted benzaldehydes (1 mmol) and freshly distilledpyrrole (2 mmol) were added and stirred at room temperature.To this reaction mixture, instead of acid, iodine wasadded (as a catalytic amount) and the color change of thereaction mixture was observed. Further, the round-bottomflask was covered with foil paper and continued stirring for5-10 min. Progress of the reaction was monitored with thehelp of thin layer chromatography (TLC) (i.e., if no reactantremains). Following which, DDQ (1 mmol) was added andthe stirring was continued for another 5 min. The product(corrole) was separated by basic alumina column chromatographywith hexane/chloroform solution. The compoundwas solid in nature with purple color and corroleswere obtained in high yield with 1:2 molar ratio in theprocess.

Reference： [1]Li, Feirong; Yang, Kexin; Tyhonas, John S.; MacCrum, Kristy A.; Lindsey, Jonathan S. [Tetrahedron, 1997, vol. 53, # 37, p. 12339 - 12360]
[2]Sharghi, Hashem; Nejad, Alireza Hassani [Helvetica Chimica Acta, 2003, vol. 86, # 2, p. 408 - 414]
[3]Sharghi, Hashem; Nejad, Ali Reza Hassani [Journal of Chemical Research - Part S, 2003, # 2, p. 87 - 88]
[4]Sharghi, Hashem; Nejad, Alireza Hassani [Tetrahedron, 2004, vol. 60, # 8, p. 1863 - 1868]
[5]Location in patent: experimental part Temelli, Baris; Unaleroglu, Canan [Tetrahedron, 2009, vol. 65, # 10, p. 2043 - 2050]
[6]Zamani, Leila; Mirjalili, Bi Bi Fatemeh [Chemistry of Heterocyclic Compounds, 2015, vol. 51, # 6, p. 578 - 581][Khim. Geterotsikl. Soedin., 2015, vol. 51, # 6, p. 578 - 581,4]
[7]Chauhan, Shive M S; Dandia, Anshu [Journal of Chemical Sciences, 2020, vol. 132, # 1]

6
[ 29162-73-0 ]
[ 141-32-2 ]
(all-E)-5,10,15,20-tetrakis[4-(2-butoxycarbonylethenyl)phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With palladium diacetate; sodium acetate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 24h;

Reference： [1]Pereira, Mariette M.; Muller, Guillermo; Ordinas, Juan Ignacio; Azenhaa, M. Emilia; Arnaut, Luis G. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 9, p. 1583 - 1588]

7
[ 29162-73-0 ]
[ 78-94-4 ]
(all-E)-5,10,15,20-tetrakis[4-(3-oxobut-1-enyl)phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; sodium acetate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 24h;

Reference： [1]Pereira, Mariette M.; Muller, Guillermo; Ordinas, Juan Ignacio; Azenhaa, M. Emilia; Arnaut, Luis G. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 9, p. 1583 - 1588]

8
[ 29162-73-0 ]
[ 493030-96-9 ]
meso-5,10,15,20-tetrakis-[4-(3,5-bis(2,5-dimethoxyphenyl)phenyl)phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In ethanol; toluene for 48h; Heating;

Reference： [1]Capitosti, Gregory J.; Guerrero, Carol D.; Binkley Jr., David E.; Rajesh, Cheruvallil S.; Modarelli, David A. [Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 247 - 261]

9
[ 29162-73-0 ]
5,10,15,20-tetrakis(4-bromophenyl)porphyrin nickel(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With nickel diacetate; acetic acid In chloroform at 120℃; for 1h;

Reference： [1]Mamane, Victor; Ledoux-Rak, Isabelle; Deveau, Sandrine; Zyss, Joseph; Riant, Olivier [Synthesis, 2003, # 3, p. 455 - 467]

10
[ 29162-73-0 ]
potassium tris(1-pyrazolyl)borate [ No CAS ]
C₄₄H₂₄Br₄N₄^(2-)*C₉H₁₀BN₆^(1-)*Yb⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With Yb[N(SiMe₃)2]3*x[LiCl(THF)3] In diethylene glycol dimethyl ether for 12h;

Reference： [1]He, Hongshan; Guo, Jianping; Zhao, Zhixin; Wong, Wai-Kwok; Wong, Wai-Yeung; Lo, Wing-Kit; Li, King-Fai; Luo, Li; Cheah, Kok-Wai [European Journal of Inorganic Chemistry, 2004, # 4, p. 837 - 845]

11
[ 29162-73-0 ]
potassium tris(1-pyrazolyl)borate [ No CAS ]
C₄₄H₂₄Br₄N₄^(2-)*C₉H₁₀BN₆^(1-)*Er⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In diethylene glycol dimethyl ether for 12h;

Reference： [1]He, Hongshan; Guo, Jianping; Zhao, Zhixin; Wong, Wai-Kwok; Wong, Wai-Yeung; Lo, Wing-Kit; Li, King-Fai; Luo, Li; Cheah, Kok-Wai [European Journal of Inorganic Chemistry, 2004, # 4, p. 837 - 845]

12
[ 29162-73-0 ]
[ 122-39-4 ]
4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrakis(N,N-diphenylaniline) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; sodium t-butanolate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl In tetrahydrofuran at 100℃; for 72h;

Reference： [1]Gao, Guangyao Y.; Chen, Ying; Zhang, X. Peter [Journal of Organic Chemistry, 2003, vol. 68, # 16, p. 6215 - 6221]

13
[ 29162-73-0 ]
[ 109-73-9 ]
5,10,15,20-tetrakis[p-(n-butylamino)phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; sodium t-butanolate In tetrahydrofuran at 100℃; for 72h;

Reference： [1]Gao, Guangyao Y.; Chen, Ying; Zhang, X. Peter [Journal of Organic Chemistry, 2003, vol. 68, # 16, p. 6215 - 6221]

14
[ 29162-73-0 ]
[ 62-53-3 ]
5,10,15,20-tetrakis[p-(N-phenylamino)phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In tetrahydrofuran at 100℃; for 72h;

Reference： [1]Gao, Guangyao Y.; Chen, Ying; Zhang, X. Peter [Journal of Organic Chemistry, 2003, vol. 68, # 16, p. 6215 - 6221]

15
[ 29162-73-0 ]
[ 100-61-8 ]
5,10,15,20-tetrakis[p-(N-methyl-N-phenylamino)phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In tetrahydrofuran at 100℃; for 72h;

Reference： [1]Gao, Guangyao Y.; Chen, Ying; Zhang, X. Peter [Journal of Organic Chemistry, 2003, vol. 68, # 16, p. 6215 - 6221]

16
[ 109-97-7 ]
[ 1122-91-4 ]
[ 29162-73-0 ]
C₄₄H₂₆Br₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	Stage #1: pyrrole; 4-bromo-benzaldehyde With methanesulfonic acid In dichloromethane for 0.5h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 0.166667h;

Reference： [1]Shaw, Janet L.; Garrison, Shana A.; Aleman, Elvin A.; Ziegler, Christopher J.; Modarelli, David A. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7423 - 7427]

17
2-[(4-bromophenyl)hydroxymethyl]-5-[(2-methoxyphenyl)hydroxymethyl]thiophene [ No CAS ]
[ 109-97-7 ]
[ 1122-91-4 ]
5-(2-methoxyphenyl)-10,15,20-tri(4-bromophenyl)-21-thiaporphyrin [ No CAS ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
3%	Stage #1: 2-[(4-bromophenyl)hydroxymethyl]-5-[(2-methoxyphenyl)hydroxymethyl]thiophene; pyrrole; 4-bromo-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane for 3h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane

Reference： [1]Stute, Silvio; Gloe, Kerstin; Gloe, Karsten [Tetrahedron, 2005, vol. 61, # 11, p. 2907 - 2912]

18
2-[(4-bromophenyl)hydroxymethyl]-5-[(2-methoxy-5-bromophenyl)hydroxymethyl]thiophene [ No CAS ]
[ 109-97-7 ]
[ 1122-91-4 ]
5-(2-methoxy-5-bromophenyl)-10,15,20-tri(4-bromophenyl)-21-thiaporphyrin [ No CAS ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
9%	Stage #1: 2-[(4-bromophenyl)hydroxymethyl]-5-[(2-methoxy-5-bromophenyl)hydroxymethyl]thiophene; pyrrole; 4-bromo-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane

Reference： [1]Stute, Silvio; Gloe, Kerstin; Gloe, Karsten [Tetrahedron, 2005, vol. 61, # 11, p. 2907 - 2912]

19
2-[(4-bromophenyl)hydroxymethyl]-5-[(2-allyloxy-5-bromophenyl)hydroxymethyl]thiophene [ No CAS ]
[ 109-97-7 ]
[ 1122-91-4 ]
5-(2-allyloxy-5-bromophenyl)-10,15,20-tri(4-bromophenyl)-21-thiaporphyrin [ No CAS ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
15%	Stage #1: 2-[(4-bromophenyl)hydroxymethyl]-5-[(2-allyloxy-5-bromophenyl)hydroxymethyl]thiophene; pyrrole; 4-bromo-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane for 3h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane

Reference： [1]Stute, Silvio; Gloe, Kerstin; Gloe, Karsten [Tetrahedron, 2005, vol. 61, # 11, p. 2907 - 2912]

20
[ 29162-73-0 ]
C₄₄H₂₄AuBr₄N₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium tetrachloroaurate(III); sodium acetate In acetic acid Heating;

Reference： [1]Che, Chi-Ming; Sun, Raymond Wai-Yin; Yu, Wing-Yiu; Ko, Chi-Bun; Zhu, Nianyong; Sun, Hongzhe [Chemical Communications, 2003, # 14, p. 1718 - 1719]

21
[ 29162-73-0 ]
[ 2510-22-7 ]
5,10,15,20-tetrakis(4-(4-pyridinylethynyl)phenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In N,N-dimethyl-formamide at 140℃; for 48h;

Reference： [1]Richardson, Christopher; Reed, Christopher A. [Journal of Organic Chemistry, 2007, vol. 72, # 13, p. 4750 - 4755]

22
[ 29162-73-0 ]
[ 153286-94-3 ]
5,10,15,20-tetrakis(4-(5-pyrinidinylethynyl)phenyl)porphyrin [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4750 - 4755

23
[ 29162-73-0 ]
[ 3032-92-6 ]
5,10,15,20-tetrakis(4-(4-cyanophenylethynyl)phenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In N,N-dimethyl-formamide at 140℃; for 48h;

Reference： [1]Richardson, Christopher; Reed, Christopher A. [Journal of Organic Chemistry, 2007, vol. 72, # 13, p. 4750 - 4755]

24
[ 29162-73-0 ]
C₆₆H₄₂N₆O₃Br₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 1h;

Reference： [1]Inoue, Mitsunori; Ikeda, Chusaku; Kawata, Yuji; Venkatraman, Sundararaman; Furukawa, Ko; Osuka, Atsuhiro [Angewandte Chemie - International Edition, 2007, vol. 46, # 13, p. 2306 - 2309]

25
[ 29162-73-0 ]
[ 371193-08-7 ]
5,10,15,20-tetrakis[4-(9,9-dihexyl-9H-fluoren-2-yl)phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate In tetrahydrofuran; water; toluene at 105℃; for 24h;

Reference： [1]Barker, Carl A.; Zeng, Xianshun; Bettington, Sylvia; Batsanov, Andrei S.; Bryce, Martin R.; Beeby, Andrew [Chemistry - A European Journal, 2007, vol. 13, # 23, p. 6710 - 6717]

26
[ 1122-91-4 ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: CF₃SO₂Cl / CH₂Cl₂ / 1 h / 20 °C 2: air / CH₂Cl₂ / 3 h / 39 °C
	Multi-step reaction with 2 steps 1: SiO₂/SOCl₂ / CH₂Cl₂ / 2 h / 20 °C 2: air / CH₂Cl₂ / 39 °C
	Multi-step reaction with 2 steps 1: PCl₅ / CH₂Cl₂ / 1 h / 20 °C 2: air / CH₂Cl₂ / 4 h / 39 °C

	Multi-step reaction with 2 steps 1: / dichloromethane / 2 h / 20 °C / Green chemistry 2: ammonium cerium (IV) nitrate / dichloromethane / 0.33 h / 20 °C / Green chemistry
	Multi-step reaction with 2 steps 1: iodine / dichloromethane / 20 °C / Inert atmosphere 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.08 h / Inert atmosphere

Reference： [1]Sharghi, Hashem; Nejad, Alireza Hassani [Tetrahedron, 2004, vol. 60, # 8, p. 1863 - 1868]
[2]Sharghi, Hashem; Nejad, Ali Reza Hassani [Journal of Chemical Research - Part S, 2003, # 2, p. 87 - 88]
[3]Sharghi, Hashem; Nejad, Alireza Hassani [Helvetica Chimica Acta, 2003, vol. 86, # 2, p. 408 - 414]
[4]Zamani, Leila; Mirjalili, Bi Bi Fatemeh [Chemistry of Heterocyclic Compounds, 2015, vol. 51, # 6, p. 578 - 581][Khim. Geterotsikl. Soedin., 2015, vol. 51, # 6, p. 578 - 581,4]
[5]Chauhan, Shive M S; Dandia, Anshu [Journal of Chemical Sciences, 2020, vol. 132, # 1]

27
[ 1122-91-4 ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: BF₃*OEt₂; NaCl / CH₂Cl₂ / 0.25 h / 25 °C 2: DDQ / CH₂Cl₂; toluene

Reference： [1]Li, Feirong; Yang, Kexin; Tyhonas, John S.; MacCrum, Kristy A.; Lindsey, Jonathan S. [Tetrahedron, 1997, vol. 53, # 37, p. 12339 - 12360]

28
[ 29162-73-0 ]
5,10,15,20-tetrakis(4-ethynylphenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / Et₃N / Pd(Ph₃P)2Cl₂ / 48 h / 90 °C 2: 86 percent / aq. KOH / tetrahydrofuran / 12 h / Ambient temperature

Reference： [1]Chan, Chi-Shing; Tse, Andy K.-S.; Chan, Kin Shing [Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 6084 - 6089]

29
[ 29162-73-0 ]
meso-Tetrakis-<4-<2-(1,4-naphthoquinonyl)>phenyl>porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 78 percent / Et₃N / Pd(Ph₃P)2Cl₂ / 48 h / 90 °C 2: 86 percent / aq. KOH / tetrahydrofuran / 12 h / Ambient temperature 3: 2.) DDQ / 1.) THF, 60 deg C, 2 d, 2.) MeOH, reflux, 1 h

Reference： [1]Chan, Chi-Shing; Tse, Andy K.-S.; Chan, Kin Shing [Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 6084 - 6089]

30
[ 29162-73-0 ]
[ 29116-34-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With zinc diacetate In methanol; dichloromethane at 20℃; for 3h;
85%	With zinc(II) acetate dihydrate In N,N-dimethyl-formamide for 5h; Inert atmosphere; Reflux;

Reference： [1]Enakieva, Yulia Y.; Bessmertnykh, Alla G.; Gorbunova, Yulia G.; Stern, Christine; Rousselin, Yoann; Tsivadze, Asian Y.; Guilard, Roger [Organic Letters, 2009, vol. 11, # 17, p. 3842 - 3845]
[2]Location in patent: experimental part Wang, Xiaochen; Wang, Haiqiao; Yang, Yi; He, Youjun; Zhang, Lei; Li, Yongfang; Li, Xiaoyu [Macromolecules, 2010, vol. 43, # 2, p. 709 - 715]

31
[ 29162-73-0 ]
C₄₄H₂₆Br₄N₆O₇Zr [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 0.32H₂O2NO₃^(1-)OZr⁽²⁺⁾ In chloroform at 15℃;

Reference： [1]Location in patent: experimental part Dehghani, Hossein; Mansournia, Mohammad Reza [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2009, vol. 74, # 2, p. 324 - 328]

32
[ 29162-73-0 ]
di(rhodium)tetracarbonyl dichloride [ No CAS ]
5,10,15,20-tetrakis(4-bromophenyl)porphinato rhodium(III) carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene for 14h; Reflux;

Reference： [1]Yamazaki, Shin-Ichi; Fujiwara, Naoko; Takeda, Sahori; Yasuda, Kazuaki [Chemical Communications, 2010, vol. 46, # 20, p. 3607 - 3609]

33
[ 29162-73-0 ]
tetra-4-bromophenylporphyrinzinc [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With zinc diacetate In methanol; chloroform for 4h; Reflux;

Reference： [1]Location in patent: experimental part Liu, Yijiang; Guo, Xia; Xiang, Na; Zhao, Bin; Huang, Hui; Li, Hui; Shen, Ping; Tan, Songting [Journal of Materials Chemistry, 2010, vol. 20, # 6, p. 1140 - 1146]

34
[ 29162-73-0 ]
[ 64413-43-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin With iron(II) chloride tetrahydrate In N,N-dimethyl-formamide at 150℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide

Reference： [1]Chen, Long; Yang, Yong; Jiang, Donglin [Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 9138 - 9143]

35
[ 29162-73-0 ]
5,10,15,20-tetra-(4-bromophenyl)-17,18-dihydroporphyrin [ No CAS ]
C₄₄H₃₀Br₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; toluene-4-sulfonic acid hydrazide In 1,4-dioxane at 120℃; for 0.416667h; Microwave irradiation; Sealed vessel;

Reference： [1]Location in patent: experimental part Nascimento, Bruno F.O.; Rocha Gonsalves, António M.d'A.; Pineiro, Marta [Inorganic Chemistry Communications, 2010, vol. 13, # 3, p. 395 - 398]

36
C₄₄H₃₀Br₄N₄ [ No CAS ]
5,10,15,20-tetra-(4-bromophenyl)-17,18-dihydroporphyrin [ No CAS ]
[ 29162-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(IV) oxide In 1,4-dioxane at 90℃; for 0.05h; Microwave irradiation; Sealed vessel;

Reference： [1]Location in patent: experimental part Nascimento, Bruno F.O.; Rocha Gonsalves, António M.d'A.; Pineiro, Marta [Inorganic Chemistry Communications, 2010, vol. 13, # 3, p. 395 - 398]

37
[ 29162-73-0 ]
[ 6147-53-1 ]
[ 178476-63-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid In chloroform at 120℃; for 1.5h;

Reference： [1]Liu, Xiaoming; Xu, Yanhong; Guo, Zhaoqi; Nagai, Atsushi; Jiang, Donglin [Chemical Communications, 2013, vol. 49, # 31, p. 3233 - 3235]

38
[ 29162-73-0 ]
[ 5970-45-6 ]
[ 29116-34-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid In chloroform at 120℃; for 1.5h;

Reference： [1]Liu, Xiaoming; Xu, Yanhong; Guo, Zhaoqi; Nagai, Atsushi; Jiang, Donglin [Chemical Communications, 2013, vol. 49, # 31, p. 3233 - 3235]

39
[ 29162-73-0 ]
[ 6046-93-1 ]
[ 63725-97-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With acetic acid In chloroform at 120℃; for 1.5h;

Reference： [1]Liu, Xiaoming; Xu, Yanhong; Guo, Zhaoqi; Nagai, Atsushi; Jiang, Donglin [Chemical Communications, 2013, vol. 49, # 31, p. 3233 - 3235]

40
[ 29162-73-0 ]
[ 10025-69-1 ]
5,10,15,20-tetrakis(4-bromophenyl)porphyrintin chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In pyridine at 120℃; for 4h; Darkness;
	With pyridine Reflux;

Reference： [1]Jiang, Jun; Luo, Rongchang; Zhou, Xiantai; Chen, Yaju; Ji, Hongbing [Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4402 - 4411]
[2]Titi, Hatem M.; Patra, Ranjan; Goldberg, Israel [Chemistry - A European Journal, 2013, vol. 19, # 44, p. 14941 - 14949]

41
[ 109-97-7 ]
[ 4521-33-9 ]
[ 1122-91-4 ]
[ 29162-73-0 ]
C₃₈H₂₀BrN₇O₆S₃ [ No CAS ]
C₄₀H₂₂Br₂N₆O₄S₂ [ No CAS ]
C₄₀H₂₂Br₂N₆O₄S₂ [ No CAS ]
C₄₂H₂₄Br₃N₅O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: pyrrole; 5-nitro-2-thiophenecarboxaldehyde; 4-bromo-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With chloranil In dichloromethane for 0.5h; Inert atmosphere; Stage #3: With triethylamine In dichloromethane Inert atmosphere;	Synthesis of nitro group containing free base porphyrins General procedure: Free base form of all the nitro group containing porphyrins were synthesized by following Lindsey’s approach [26] with minor modification. In a typical procedure, to a mixture of 3-methylthiophene-2-aldehyde (0.82 mL, 7.6 mmol) and 5-nitrothiophene-2-aldehyde (1.2 g, 7.6 mmol) in 600 mL of dichloromethane, pyrrole(1 mL, 15.2 mmol) was added under N2 atmosphere. To this, BF3 etherate (0.62 mL, 5.06 mmol) was added and the reaction mixture was stirred for one hour at room temperature. At the end of the period, p-chloranil (3.73 g, 15.2 mmol) was added and the stirring was continued for another half an hour. Following this, triethylamine (0.7 mL, 5.06 mmol) was added and further stirred for one hour. The reaction mixture was then adsorbed on 200 g of silicagel (230-400 mesh) and the mixture of porphyrins (H2TaNThP,4a, 4b, 4c, 4d and 4e; Fig. 1) was eluted using chloroform. The solution was then concentrated by rotary evaporation and the porphyrins were separated by column chromatography using chloroform as the eluent. The yield of all products is given in supporting information.The compounds were characterized by UV visible, 1HNMR and mass spectral techniques. UV visible spectral details are givenin Table 1. 1H NMR and mass spectral details of all the synthesized compounds are given in supporting information.

Reference： [1]Prasath, Rangaraj; Bhavana, Purushothaman [Journal of Molecular Structure, 2014, vol. 1079, p. 486 - 493]

42
[ 29162-73-0 ]
p-(N,N-di-n-octylamino)phenylacetylene [ No CAS ]
C₁₄₀H₁₇₈N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In N,N-dimethyl-formamide at 90℃; for 20h;

Reference： [1]Liang, Pengxia; Du, Zhengcai; Wang, Dong; Yang, Zhou; Sheng, Huiyun; Liang, Shuqiong; Cao, Hui; He, Wanli; Yang, Huai [ChemPhysChem, 2014, vol. 15, # 16, p. 3523 - 3529]

43
[ 29162-73-0 ]
[ 4529-04-8 ]
5,10,15,20-tetrakis(4-propynylphenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide In tetrahydrofuran at 85℃; Schlenk technique; Glovebox; Inert atmosphere;

Reference： [1]Lu, Guolong; Yang, Haishen; Zhu, Youlong; Huggins, Tyler; Ren, Zhiyong Jason; Liu, Zhenning; Zhang, Wei [Journal of Materials Chemistry A, 2015, vol. 3, # 9, p. 4954 - 4959]

44
[ 29162-73-0 ]
[ 96-10-6 ]
C₄₄H₂₆AlBr₄ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: diethylaluminium chloride In dichloromethane at 20℃; for 1h; Inert atmosphere;

Reference： [1]Sheng, Xingfeng; Guo, Hongchen; Qin, Yusheng; Wang, Xianhong; Wang, Fosong [RSC Advances, 2015, vol. 5, # 40, p. 31664 - 31669]

45
[ 29162-73-0 ]
[ 762-04-9 ]
5,10,15,20-tetrakis(4-phosphonatophenyl)porphyrin octaethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In toluene at 80℃; for 24h; Inert atmosphere;	The second step is the formation of a C-P bond. In an anhydrous and oxygen-free environment, 5,10,15,20-tetrakis(4-bromophenyl)porphyrin 150 mg (ie 0.16 mmol) and tetrakis(triphenylphosphine)palladium 37.4 mg (ie 0.034 mmol, 0.2 equivalent) was added to a dry 50 ml two-necked round bottom flask; Under a nitrogen atmosphere, 20 ml of toluene, 0.088 ml of diethyl phosphite (ie, 0.71 mmol, 4.4 equivalents), and 0.10 ml of triethylamine (ie, 0.71 mmol, 4.4 equivalents) were separately added by a syringe. The reaction flask was placed in an oil bath at 80 ° C and stirred under heating for 24 hours. Then, toluene, triethylamine and the remaining reactants were distilled off under reduced pressure, and the solid matter after distillation was separated by column chromatography. The eluent was ethyl acetate/petroleum ether (1:1; V/V). The purple solid tetrakis(diethyl phosphate phenyl) porphyrin 143 mg was obtained in a yield of 77%. The formation reaction of the C-P bond is repeated. The purpose of this operation is to complete the incomplete trisubstituted, disubstituted and monosubstituted products of the C-P bond coupling. The starting material used was about 40 mg of incompletely substituted porphyrin separated in the first stage C-P bond coupling. The amount of the other reactants, catalyst and solvent was reduced in the same manner as above, and the operation was repeated. The purple solid tetrakis(diethyl phosphate phenyl) porphyrin 34 mg was obtained in a yield of 81%. The coupling operation of the compound tetrakis(diethyl phosphate phenyl) porphyrin was 177 mg, and the total yield was 95%.
26%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran; toluene Reflux;

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN109705161, 2019, A Location in patent: Paragraph 0040; 0041; 0044; 0045
[2]Venkatramaiah; Pereira, Carla F.; Mendes, Ricardo F.; Paz, Filipe A. Almeida; Tom, Joäo P. C. [Analytical Chemistry, 2015, vol. 87, # 8, p. 4515 - 4522]

46
[ 29162-73-0 ]
C₄₄H₂₄Li₄N₄^(2-)*2Li⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In diethyl ether at -50℃;

Reference： [1]Önal, Emel; Ahsen, Vefa; Pécaut, Jacques; Luneau, Dominique; Hirel, Catherine [Tetrahedron Letters, 2015, vol. 56, # 37, p. 5157 - 5160]

47
[ 29162-73-0 ]
[ 557-34-6 ]
[ 29116-34-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	In N,N-dimethyl-formamide at 180℃; for 0.5h; Microwave irradiation;	meso-tetrakis(4-bromophenyl)porphyrinato Zn(II)(Br₄TPPZn) 2.5g of Br4TPPH2 (2.69 mmol)and 0.6 g (2.69 mmol) of Zn(OAc)2 in 50 ml of DMF were placed in a 100mL flask. The reaction was heat by MW irradiation at 180 oC during30 min. and the completion of the reaction was monitored by TLC (DCM/n-Hexane 1/1). The reaction mixture was cooled toroom temperature and adding drop by drop to 100 mL of water. The resultingsolid was dissolved in DCM, dried with Na2SO4. The pink solidwas purified by column chromatography on silica gel eluting by n-Hexane/DCM 2:1follow by n-Hexane/DCM 1:1 system and dried under vacuum over a night. Yield 96%. IR n (cm-1): 3063 (CH Ar ), 1477 (C=N), 1391-1336 (=C-N),1068 (C-Hpyrrole), 996(C-H por. ring), 793(C-H pyr. ring). 1HNMR (CDCl3), δ (ppm) = 7.84 (d, 8H, CHAr-phenyl),7.99 (d, 8H, CHAr-phenyl),8.87 (s, 8H, CHpyrrole). 13C NMR (CDCl3),δ (ppm) =129.56(CH-C3),131.92 (CH-Cβ), 135.54 (CH-C2). UV-visible (CHCl3),λmax(nm) = 419; 545 Mass (ESI-MS, m/z): C44H24N4Br4Zn([M+H]+),calcd: 993,6900, found: 994.5598
95%	In dichloromethane at 60℃;	5 Example 5 Take 2 g of the porphyrin crystals obtained in Example 1, dissolve in 200 mL of dichloromethane,0.6g of zinc acetate was added, and the reaction was carried out overnight for more than 12h under the condition of heating in a water bath at 60°C.After suction filtration, extraction and drying, the bright purple powder obtained is the zinc-porphyrin complex ZnBrTPP of the present invention (yield: 95%).
80%	In chloroform; N,N-dimethyl-formamide for 0.133333h; Reflux;	Zn(II) 5,10,15,20-Tetra(4-bromophenyl)porphyrinate (3). 0.04 g (0.043 mmol) of porphyrin 1 and 0.079 g (0.43 mmol) of Zn(OAc)2 were dissolved in a mixture of 8 mL of chloroform and 2 mL of DMF, the reaction mixture was heated till boiling, boiled for 8 min, then cooled, water was added, organic layer was separated, washed with water, dried with Na2SO4, evaporated to minimal quantity, chromatographed on aluminum oxide eluting with methylene chloride, then with chloroform. Yield 0.034 g (0.0344 mmol) (80%), Rf 0.60. 1H NMR spectrum, δ, ppm: 7.93 d (8H, HmPh, J 7.60 Hz), 8.10 d (8H, HoPh, J 7.70 Hz), 8.97 s (8Hpyrr. ring). Mass spectrum, m/z (Irel, %): 993.42 (4.7) [M]+, 837 (4.5), 619 (6.2), 485 (11.5), 457 (100), 441 (72.8).

Reference： [1]Önal, Emel; Ahsen, Vefa; Pécaut, Jacques; Luneau, Dominique; Hirel, Catherine [Tetrahedron Letters, 2015, vol. 56, # 37, p. 5157 - 5160]
[2]Current Patent Assignee: UNIV HEFEI - CN114380839, 2022, A Location in patent: Paragraph 0051-0053
[3]Chizhova; Zvezdina; Kumeev; Mamardashvili, N. Zh. [Russian Journal of Organic Chemistry, 2015, vol. 51, # 11, p. 1649 - 1651][Zh. Org. Khim., 2015, vol. 51, # 11, p. 1678 - 1680,3]

48
[ 29162-73-0 ]
[ 33513-42-7 ]
5,10,15,20-tetrakis(4-formylphenyl)-21H,23H-porphyrin [ No CAS ]
meso-5,10,15-(4-formylphenyl)-20-phenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 5%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin In diethyl ether at 20℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: N,N-dimethyl-formamide With n-butyllithium In diethyl ether at -50 - 20℃; for 3h; Schlenk technique; Inert atmosphere;	meso-tetrakis(4-formlyphenyl)porphyrin((CHO)₄TPPH2) 400 mg of meso-tetrakis(4-bromophenyl)porphyrin (0.4 mmol) in a schlenk tube was driedby purge-and-refill for at least three time (nitrogen(g)/vacuum). Under nitrogen (g), 50 mL of dry diethylether was added with asyringe at room temperature. The purple solution was placed in a liquid nitrogen-acetonebath at -50 oC for 10 min and 5 mL (6.25 mmol) of n-buthyllithium was added, giving rise to a greenresulting mixture that was stirred for 3 h at -50 oC. Then, 5 ml (37.5 mmol) of dry DMF was added. The cooling bath was removed andthe green-blue reaction mixture was stirred for 3 h more. At room temperature,250 mL of HCl 5 % was added and vigorously stirred for 15 min. The mixture was neutralized by NH4OH. The resulting pink-red emulsion was extractedwith chloroform, dried with Na2SO4 and evaporated todryness at 45 oC. The mixture was separated by column chromatographyin diethylether/ DCM 1:9 to give 80% of (CHO)4TPPH2 and 5%of triformylated meso-5,10,15-(4-formylphenyl)-20-phenylporphyrin. FT-IR, n (cm-1): 3312 (NH),3105 (CHAr ), 1694(C=O),1599(C=Cphenyl), 1566(C=Cpyrrole), 1472 (C=N),1383 (=C-N), 1168, (CHpyrrole), 965(CH porp. ring) , 804(CH pyr. ring), 728 (NH bending).1H NMR (CDCl3), δ (ppm)=-2.79 (s, 2H, NH),8.32 (d, 8H, CHAr-phenyl),8.40 (d, 8H, CHAr-phenyl), 8.83 (s, 8H, CHpyrrole),10.40(s, 4H, CHO). 13C NMR (CDCl3),δ (ppm)= 118.24(Cmeso),127.09(CH-C3), 134.10 (CH-Cβ), 134.82 (CH-C2),147.05 (Cα). UV-visible (CHCl3),λmax(nm) = 419; 523;559; 600; 653. Mass (HR-ESI, m/z): C48H31N4O4([M+H]+), calcd: 727,2340, found: 727.2348 (see Figure S7).

Reference： [1]Önal, Emel; Ahsen, Vefa; Pécaut, Jacques; Luneau, Dominique; Hirel, Catherine [Tetrahedron Letters, 2015, vol. 56, # 37, p. 5157 - 5160]

49
[ 51921-56-3 ]
[ 29162-73-0 ]
[ 159564-89-3 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: bis(benzonitrile)dichloroplatinum(II); 5,10,15,20-tetrakis(p-bromophenyl)porphyrin With sodium proprionate In chloroform for 2h; Reflux; Stage #2: With hydrogenchloride In acetonitrile at 70℃; for 1h;
66%	With sodium proprionate In chlorobenzene for 0.666667h; Reflux;	Synthesis of [5,10,15,20-tetrakis(4-bromophenyl)porphyrinato]platinum(II) (1e(Pt)). A mixture of 5,10,15,20-tetrakis(4-bromophenyl)porphyrin(1e(2H)) (37.3 mg, 0.040 mmol), PtCl2(PhCN)2 (2d) (28.3 mg, 0.060 mmol), and sodium propionate (19.3 mg, 0.20 mmol) in chlorobenzene (1 mL) was refluxed for 40 min under atmospheric conditions. The reaction mixture was directly poured on top of a silica gel column, and then eluted with chloroform. After the removal of solvent under reduced pressure, acetonitrile (2 mL) and concentrated HCl(1 drop) was added to the crude product. The resultant suspension was stirred at 70 °C for 0.5h, and then cooled to room temperature. The precipitate was collected by filtration, washed with acetonitrile, and dried under vacuum to give 1e(Pt) as brown powder (29.9 mg, 0.027mmol, 66%). Although this compound has been already reported, its NMR data have not been reported.S11 1H NMR (500 MHz, CDCl3) δ (ppm) = 8.75 (s, 8H, PorHβ), 8.01 (d, J = 8.3 Hz,8H, ArH), 7.89 (d, J = 8.3 Hz, 8H, ArH).13C NMR (100 MHz, CDCl3) δ (ppm) = 140.7 (Cq), 140.0 (Cq), 135.2 (CH), 130.8 (CH), 130.1 (CH), 122.7 (Cq), 121.2 (Cq).

Reference： [1]He, Qichuan; Huang, Senhe; Kang, Jialing; Liang, Haiwei; Lu, Chenbao; Su, Yuezeng; Zhu, Jinhui; Zhuang, Xiaodong [Chemical Communications, 2022, vol. 58, # 14, p. 2339 - 2342]
[2]Yamashita, Ken-Ichi; Katsumata, Natsuki; Tomita, Shohei; Fuwa, Miki; Fujimaki, Keisuke; Yoda, Takuya; Hirano, Daisuke; Sugiura, Ken-Ichi [Chemistry Letters, 2015, vol. 44, # 4, p. 492 - 494]

50
[ 29162-73-0 ]
2-bromo-5,10,15,20-tetra(4-bromophenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With N-Bromosuccinimide In chloroform; N,N-dimethyl-formamide for 0.0833333h; Reflux;	2-Bromo-5,10,15,20-tetra(4-bromophenyl)porphyrin (2) To 0.04 g (0.043 mmol) of porphyrin 1 in a mixture of 8 mL of CHCl3 and 2 mL of DMF was added 0.0153 g (0.086 mmol) of NBS, the mixture was stirred, heated till boiling, boiled at reflux for 5 min. In the reaction mixture pyridine was added, the mixture was cooled, water was added, organic layer was separated, carefully washed with water, dried with Na2SO4, evaporated to minimal quantity, chromatographed on aluminum oxide eluting with a mixture methylene chloride-hexane, 1 : 1, then with methylene chloride. Yield 0.027 g (0.0267 mmol) (63%). 1H NMR spectrum, δ, ppm: -2.95 s (2H, NH), 7.87-7.95 m (8H, mPh), 8.02 m (2H), 8.08 m (6H, HoPh), 8.68-8.75 m (2H), 8.78-8.84 m (2H), 8.85 s (1H), 8.88-8.91 s (2Hpyrr. ring).

Reference： [1]Chizhova; Zvezdina; Kumeev; Mamardashvili, N. Zh. [Russian Journal of Organic Chemistry, 2015, vol. 51, # 11, p. 1649 - 1651][Zh. Org. Khim., 2015, vol. 51, # 11, p. 1678 - 1680,3]

51
[ 29162-73-0 ]
zinc(II) 2-bromo-5,10,15,20-tetra(4-bromophenyl)porphyrinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide; chloroform / 0.08 h / Reflux 2: N,N-dimethyl-formamide; chloroform / 0.07 h / Reflux

Reference： [1]Chizhova; Zvezdina; Kumeev; Mamardashvili, N. Zh. [Russian Journal of Organic Chemistry, 2015, vol. 51, # 11, p. 1649 - 1651][Zh. Org. Khim., 2015, vol. 51, # 11, p. 1678 - 1680,3]

52
[ 29162-73-0 ]
zinc(II) 2,3,12,13-tetrabromo-5,10,15,20-tetra(4-bromophenyl)porphyrinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; chloroform / 0.13 h / Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide; chloroform / Reflux

Reference： [1]Chizhova; Zvezdina; Kumeev; Mamardashvili, N. Zh. [Russian Journal of Organic Chemistry, 2015, vol. 51, # 11, p. 1649 - 1651][Zh. Org. Khim., 2015, vol. 51, # 11, p. 1678 - 1680,3]

53
[ 29162-73-0 ]
zinc(II) 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetra(4-bromophenyl)porphyrinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; chloroform / 0.13 h / Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide; chloroform / Reflux 3: N-Bromosuccinimide / N,N-dimethyl-formamide; chloroform / 0.27 h / Reflux

Reference： [1]Chizhova; Zvezdina; Kumeev; Mamardashvili, N. Zh. [Russian Journal of Organic Chemistry, 2015, vol. 51, # 11, p. 1649 - 1651][Zh. Org. Khim., 2015, vol. 51, # 11, p. 1678 - 1680,3]

54
[ 29162-73-0 ]
[ 536-74-3 ]
meso-tetrakis(4-phenylethynyl)phenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With palladium diacetate; triethylamine; triphenylphosphine In tetrahydrofuran at 91℃; Inert atmosphere;

Reference： [1]Önal, Emel; Ay, Zeynep; Yel, Zübeyde; Ertekin, Kadriye; Gürek, Ayşe Gül; Topal, Sevinc Zehra; Hirel, Catherine [RSC Advances, 2016, vol. 6, # 12, p. 9967 - 9977]

55
[ 29162-73-0 ]
bis(acetylacetonato)palladium(II) [ No CAS ]
[ 112592-51-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	In 1-methyl-pyrrolidin-2-one at 180℃; for 0.25h; Schlenk technique; Microwave irradiation;

Reference： [1]Önal, Emel; Ay, Zeynep; Yel, Zübeyde; Ertekin, Kadriye; Gürek, Ayşe Gül; Topal, Sevinc Zehra; Hirel, Catherine [RSC Advances, 2016, vol. 6, # 12, p. 9967 - 9977]

56
platinum(II) bis(acetylacetonate) [ No CAS ]
[ 29162-73-0 ]
[ 159564-89-3 ]

Yield	Reaction Conditions	Operation in experiment
25%	In 1-methyl-pyrrolidin-2-one at 110℃; for 0.75h; Schlenk technique; Microwave irradiation;

Reference： [1]Önal, Emel; Ay, Zeynep; Yel, Zübeyde; Ertekin, Kadriye; Gürek, Ayşe Gül; Topal, Sevinc Zehra; Hirel, Catherine [RSC Advances, 2016, vol. 6, # 12, p. 9967 - 9977]

57
[ 29162-73-0 ]
manganese(ll) chloride [ No CAS ]
[ 205596-98-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	In N,N-dimethyl-formamide for 0.25h; Reflux;	2.7. Synthesis of 5,10,15,20-tetra-(4-bromophenyl)porphyrin chlorideMn(III) (17) (a) 0.02 g (0.0215 mmol) of 4 was dissolved in 10 mL of DMF, 0.054 g (0.430 mmol) ofMnCl2 was added, and the reaction mixture was refluxed with stirring for 15 min. Darkgreen precipitate was obtained and processed in a similar manner to 11. Yield: 74%(0.016 g, 0.0157 mmol). (b) 0.02 g (0.0192 mmol) of 9, 0.048 g (0.384 mmol) of MnCl2,and 10 mL of DMF were heated to a boil and boiled for 20 s. Yield: 89% (0.0175 g,0.0171 mmol). Found %: C 51.75; H 2.32; N 5.43. C44H24N4ClBr4Mn. Calculated %: C51.88; H 2.38; N 5.50. Mass spectrum m/z (Irel, %): 982.68 (75) [M-Cl] +was calculatedfor C44H24N4Br4Mn - 983.3. 1H NMR (CDCl3,δ , ppm): 8.60 br. s. (8H, pyrrole ring), 8.35br. s. (16H, ortho-C6H5 and meta-C6H5).
	Inert atmosphere;

Reference： [1]Chizhova, Natalya Vasil’evna; Maltceva, Olga Valentinovna; Zvezdina, Svetlana Veniaminovna; Mamardashvili, Nugzar Zhoraevich; Koifman, Oscar Iosifovich [Journal of Coordination Chemistry, 2018, vol. 71, # 19, p. 3222 - 3232]
[2]Ikezaki, Akira; Nakamura, Mikio [Journal of Porphyrins and Phthalocyanines, 2016, vol. 20, # 1-4, p. 318 - 330]

58
[ 29162-73-0 ]
cobalt(II) acetate [ No CAS ]
[ 178476-63-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide for 0.00833333h; Reflux;	Co(II) 5,10,15,20-tetra-(4-chlorophenyl)por-phyrinate (1). General procedure: A mixture of 0.04 g (0.065 mmol) tetra-(4-chlorophenyl)porphyrin and 0.096 g (0.65 mmol) of (Ac) 2 in 30 mL of DMF was boiled for 30 s and then cooled to ambient. The mixture was poured into water, and NaCl was added. The precipitate was filtered off, washed with water, dried, and purified by chromatography on alumina eluting with dichloro-methane. Yield 0.033 g (0.0407 mmol, 77%).
62%	In methanol; chloroform for 1.5h; Reflux;	Cobalt(II) 5,10,15,20-tetra-(4-bromophenyl)porphyrinate(4). 0.038 g (0.215 mmol) of Co(OAc)2 dissolved in 10 mL of methanol was added to asolution of 0.02 g (0.0215 mmol) of porphyrin 1 in15 mL of chloroform. The reaction mixture wasrefluxed during 1.5 h and then cooled; distilled waterwas added to the mixture; the organic layer wasseparated off, washed with water, dried over Na2SO4,and evaporated. The residue was subject to chromatographyon alumina with chloroform and then reprecipitatedfrom methanol. Yield 0.013 g (0.013 mmol,62%). 1H NMR spectrum, δ, ppm: 15.87 br.s. (8,pyrrole), 12.96 br.s (8, o), 10.08 br.s (8, m).Mass spectrum, m/z (Irel, %): 986 (70) [M - H]+.

Reference： [1]Ivanova, Yu. B.; Chizhova; Khrushkova, Yu. V.; Rusanov; Mamardashvili, N. Zh. [Russian Journal of General Chemistry, 2019, vol. 89, # 3, p. 459 - 465][Zh. Obshch. Khim., 2019, vol. 89, # 3, p. 434 - 440,7]
[2]Chizhova; Zvezdina; Mamardashvili, N. Zh. [Russian Journal of General Chemistry, 2016, vol. 86, # 5, p. 1091 - 1094][Zh. Obshch. Khim., 2016, vol. 86, # 5, p. 829 - 832,4]

59
palladium(II) acetylacetonate [ No CAS ]
[ 29162-73-0 ]
[ 112592-51-5 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 110℃; for 24h;

Reference： [1]Hynek, Jan; Rathouský, Jiří; Demel, Jan; Lang, Kamil [RSC Advances, 2016, vol. 6, # 50, p. 44279 - 44287]

60
[ 29162-73-0 ]
iron(II) chloride tetrahydrate [ No CAS ]
[ 64413-43-0 ]

Yield	Reaction Conditions	Operation in experiment
75.9%	In N,N-dimethyl-formamide for 6h; Reflux;
	In N,N-dimethyl-formamide for 4h; Reflux;	2.2.5. Preparation of iron-based porphyrins General procedure: In a typical synthetic process, 0.16 g of porphyrin ligand synthesized above was dissolved in 30 mL of DMF. The mixed solution was heated at reflux temperature under magnetic stirring. Then FeCl2·4H2O (fourtimes the molar quantities of the ligand) was added into the solution in three batches. The reaction was carried out for 4 h and the solvent was removed by reduced pressure distillation, then hydrochloric acid was added slowly until the brown solid on the reactor wall was full dissolved.The mixture was immersed in deionized water overnight, collected via filtration and washing with hydrochloric acid and deionized water, and dried in oven at 80 °C for 8 h.

Reference： [1]Dou, Zhiyu; Xu, Li; Zhi, Yongfeng; Zhang, Yuwei; Xia, Hong; Mu, Ying; Liu, Xiaoming [Chemistry - A European Journal, 2016, vol. 22, # 29, p. 9919 - 9922]
[2]Xie, Yongdi; Huang, Yi; Wu, Chunyan; Yuan, Wenwen; Xia, Yongmei; Liu, Xiang; Wang, Haijun [Molecular catalysis, 2018, vol. 452, p. 20 - 27]

61
[ 29162-73-0 ]
[ 5970-45-6 ]
5,10,15,20-tetrakis(4-bromophenyl)porphyrin zinc(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanol In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

Reference： [1]Guo, Bing; Cai, Xiaolei; Xu, Shidang; Fateminia, Syed Mohammad Ali; Liu, Jie; Liang, Jing; Feng, Guangxue; Wu, Wenbo; Liu, Bin [Journal of Materials Chemistry B, 2016, vol. 4, # 27, p. 4690 - 4695]

62
[ 29162-73-0 ]
[ 5970-45-6 ]
[ 29116-34-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol; chloroform at 77℃; for 2h; Reflux;
90%	With acetic acid In chloroform at 120℃; for 1.5h;
87%	In chloroform at 120℃; for 2.5h; Sealed tube; Microwave irradiation;

Reference： [1]Covezzi; Orbelli Biroli; Tessore; Forni; Marinotto; Biagini; Di Carlo; Pizzotti [Chemical Communications, 2016, vol. 52, # 85, p. 12642 - 12645]
[2]Cui, Di; Yao, Chan; Xu, Yanhong [Chemical Communications, 2017, vol. 53, # 83, p. 11422 - 11425]
[3]Ferrero, Sergio; Barbero, Héctor; Miguel, Daniel; García-Rodríguez, Raúl; Álvarez, Celedonio M. [RSC Advances, 2020, vol. 10, # 59, p. 36164 - 36173]

63
[ 29162-73-0 ]
(E)-1-(1-(tert-butylperoxy)-3,3,3-trifluoropropyl)-4-styrylbenzene [ No CAS ]
5,10,15,20-tetrakis(4-(((E)-4-((E)-styryl)styryl)phenyl))-21H,23H-porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.7%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;	1 2.6. Synthesis of porphyrin dendrimers of second generation via Heckreaction General procedure: A mixture of 4 or 8 (3.8 mmol), and 12 or 13 (0.067 mol), Pd(OAc)2 (1.3 mmol), and tri-o-tolylphosphine POT (3.28 mmol) inEt3N/DMF 1:4 (25 mL) was stirred under nitrogen atmosphere at120 °C for 24 h. After cooling, the resulting mixture wasfiltered andthe solvents evaporated. The crude product was purified by columnchromatography (silica gel 70-230 mesh) using hexane:dichloromethane1:1 as eluent, to give the porphyrins 14 or 15.2.6.1. 5,10,15,20-Tetrakis(4-((E)-4-((E)-styryl)styryl)phenyl))-21H,23H-porphyrin 14(0.16 g, 0.11 mmol) as a purple solid in 53.7% yield. m.p: >300 °C.UV-vis, (CHCl3), l (nm): 244, 361, 430, 517, 556, 593, 649. IR (KBr,cm1): 3426, 3378, 3307, 3021, 2920, 2850, 1727, 1671, 1593, 1508,1445, 1370, 1293, 1177, 1042, 796, 748, 688, 543. 1H NMR (700 MHz,CDCl3), δH (ppm):2.71 (s, 2H, NH), 7.178 (d, 16H, CHCH,J = 17.5 Hz), 7.28 (t, 4H, Ar, J = 7.0 Hz), 7.39 (t, 8H, Ar, J = 7.0 Hz), 7.44(d, 8H, Ar, J = 8.4 Hz), 7.56 (d, 8H, Ar, J = 7.0 Hz), 7.59 (d, 8H, Ar,J = 7.0 Hz), 7.66 (d, 8H, Ar, J = 7.7 Hz), 7.91 (d, 8H, Ar, J = 6.3 Hz), 8.92(s, 8H, b-Py). 13C NMR (175 MHz, CDCl3) δC (ppm): 124.9 (Ar), 126.6(Ar), 127.1 (Ar), 127.7 (Ar), 128.3 (-CH = ), 128.7 (Pyipso), 130.1(CH), 135.1 (b-Py), 136.7 (Aripso), 136.7 (Aripso), 136.8 (Aripso),137.3 (Aripso). ESI MS (m/z): 1430.5 (M + 1). Anal. Elem. calc. for:C108H78N4: C, 90.60; H, 5.49; N, 3.91%. Found: C, 90.58; H, 5.47; N,3.90%.

Reference： [1]Organista-Mateos, Ulises; Martínez-Klimov, Mark E.; Pedro-Hernández, Luis D.; Borja-Miranda, Andrés; Cortez-Maya, Sandra; Hernández-Ortega, Simón; Martínez-García, Marcos [Journal of Photochemistry and Photobiology A: Chemistry, 2017, vol. 343, p. 58 - 65]

64
[ 863238-73-7 ]
[ 29162-73-0 ]
5,10,15,20-tetrakis(4-(1-trityl-pyrazol-4-yl)phenyl)porphyrin [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 211 - 217

65
[ 29162-73-0 ]
[ 1539-42-0 ]
C₉₂H₇₄N₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide In acetonitrile for 8h; Reflux;	5,10,15,20-tetrabromophenyl porphyrin (TBrTPP) (93 mg, 0.1 mmol),Di-2-picolylamine (DPA) (70.5 μL, 0.4 mmol),Potassium iodide (66.7 mg, 0.4 mmol),Potassium carbonate (55 · 2 mg, 0.4 mmol)Dissolved in 10 mL of acetonitrile,After heating and refluxing for 8h,Thin layer chromatography (TLC)(Developing solvent ratio dichloromethane: methanol = 9: 1 (v / v)),No verification after 5,10,15,20_ four aminophenyl porphyrin raw materials remaining,Rotary evaporation of the solvent,Silica gel chromatography crude product(Developing solvent ratio dichloromethane: methanol = 9: 1 (v / v)),The first ribbon product was collected.Nuclear magnetic resonance (1H NMR) (Figure 1)And fluorescence spectra (Figure 2) to verify its chemical structure.1 H NMR solvent using deuterated DMSO (DMSO-d6), the parameters of the fluorescence spectrometer are as follows: the excitation wavelength is 420nm; the receiving wave band is 600nm ~ 725nm

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY CITY COLLEGE - CN106317062, 2017, A Location in patent: Paragraph 0040

66
[ 29162-73-0 ]
[ 96-10-6 ]
C₄₄H₂₄AlBr₄ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.5%	In hexane; dichloromethane at 25℃; for 1h; Inert atmosphere;	2 In the 25 °C, N2Under the protection of the 20 ml dry dichloromethane, 0.9g four (4 - bromophenyl) porphyrin (1mmol) is added to the 50 ml round bottom three flasks, stirring until the solid completely dissolved, add 1.5 ml diethyl aluminum chloride solution (1 mol/L hexane solution, 1.5eq) stirring 1h. The above-mentioned liquid is distilled under reduced pressure to remove the solvent, the obtained crude product via a chromatographic column separation [fixed phase: aluminum oxide; mobile phase: dichloromethane; elution phase: methylene chloride/methanol (volume ratio)=10:1], to obtain four (4 - bromophenyl) porphyrin chloride, treated as complex 3, complex 3 the conversion rate of 93.5%

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104327036, 2017, B Location in patent: Paragraph 0119

67
[ 29162-73-0 ]
[ 1118-46-3 ]
butyl(5,10,15,20-tetrakis(4-bromophenyl)porphyrinato)tin(IV) chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In toluene at 90℃; for 3h; Inert atmosphere;

Reference： [1]Yaman, Hanifi; Kayan, Asgar [Journal of Porphyrins and Phthalocyanines, 2017, vol. 21, # 3, p. 231 - 237]

68
[ 29162-73-0 ]
nickel dichloride [ No CAS ]
[ 122-52-1 ]
C₄₄H₃₂N₄NiO₁₂P₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin; nickel dichloride at 170℃; Inert atmosphere; Stage #2: triethyl phosphite at 170℃; for 24.5h; Inert atmosphere;

Reference： [1]Rhauderwiek, Timo; Wolkersdörfer, Konrad; Øien-ØDegaard, Sigurd; Lillerud, Karl-Petter; Wark, Michael; Stock, Norbert [Chemical Communications, 2018, vol. 54, # 4, p. 389 - 392]

69
[ 109-97-7 ]
2-(2-nitro-1-(1H-pyrrol-2-yl)ethyl)-5-(phenyl(1H-pyrrol-2-yl)methyl)-1H-pyrrole [ No CAS ]
[ 1122-91-4 ]
[ 29162-73-0 ]
5,10,15-tris(4-bromophenyl)-20-(nitromethyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 13% 2: 9%	Stage #1: 4-bromo-benzaldehyde With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-(2-nitro-1-(1H-pyrrol-2-yl)ethyl)-5-(phenyl(1H-pyrrol-2-yl)methyl)-1H-pyrrole In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #3: pyrrole Further stages;

Reference： [1]Seyitdanlioglu, Pinar; Altundal, Gulberil; Cinar, Seda; Unaleroglu, Canan [New Journal of Chemistry, 2018, vol. 42, # 17, p. 14163 - 14169]

70
[ 29162-73-0 ]
[ 54060-30-9 ]
5,10,15,20-tetra[4-[(3-aminophenyl)ethynyl]phenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine In N,N-dimethyl acetamide

Reference： [1]Shi, Kaixiang; Song, Ningning; Zou, Yongcun; Zhu, Shiyang; Tan, Haiwei; Tian, Ye; Zhang, Bo; Yao, Hongyan; Guan, Shaowei [Polymer, 2019, vol. 169, p. 160 - 166]

71
[ 29162-73-0 ]
2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetra(4-bromophenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 0.01 h / Reflux 2: N-chloro-succinimide / chloroform; N,N-dimethyl-formamide / 0.1 h / Reflux 3: perchloric acid; sulfuric acid / chloroform / 8 h / 20 °C

Reference： [1]Ivanova, Yu. B.; Chizhova; Khrushkova, Yu. V.; Rusanov; Mamardashvili, N. Zh. [Russian Journal of General Chemistry, 2019, vol. 89, # 3, p. 459 - 465][Zh. Obshch. Khim., 2019, vol. 89, # 3, p. 434 - 440,7]

72
[ 29162-73-0 ]
C₄₄H₁₆Br₄Cl₈N₄Zn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 0.01 h / Reflux 2: N-chloro-succinimide / chloroform; N,N-dimethyl-formamide / 0.1 h / Reflux 3: perchloric acid; sulfuric acid / chloroform / 8 h / 20 °C 4: perchloric acid / acetonitrile

Reference： [1]Ivanova, Yu. B.; Chizhova; Khrushkova, Yu. V.; Rusanov; Mamardashvili, N. Zh. [Russian Journal of General Chemistry, 2019, vol. 89, # 3, p. 459 - 465][Zh. Obshch. Khim., 2019, vol. 89, # 3, p. 434 - 440,7]

73
[ 29162-73-0 ]
Co(II) 2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetra(4-bromophenyl)porphyrinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 0.01 h / Reflux 2: N-chloro-succinimide / chloroform; N,N-dimethyl-formamide / 0.1 h / Reflux

Reference： [1]Ivanova, Yu. B.; Chizhova; Khrushkova, Yu. V.; Rusanov; Mamardashvili, N. Zh. [Russian Journal of General Chemistry, 2019, vol. 89, # 3, p. 459 - 465][Zh. Obshch. Khim., 2019, vol. 89, # 3, p. 434 - 440,7]

74
[ 29162-73-0 ]
[ 33513-42-7 ]
5,10,15,20-tetrakis(4-formylphenyl)-21H,23H-porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin With n-butyllithium In diethyl ether at -50 - 0℃; for 8.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether at -50 - 20℃;
35%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin With n-butyllithium In diethyl ether at -50 - 0℃; for 8.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether at -50 - 20℃; Inert atmosphere;
31%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin With n-butyllithium In diethyl ether at -78 - 0℃; for 3h; Stage #2: N,N-dimethyl-formamide In diethyl ether at -78 - 20℃; for 3h;

Reference： [1]Biswal, Bishnu P.; Valligatla, Sreeramulu; Wang, Mingchao; Banerjee, Tanmay; Saad, Nabil A.; Mariserla, Bala Murali Krishna; Chandrasekhar, Naisa; Becker, Daniel; Addicoat, Matthew; Senkovska, Irena; Berger, Reinhard; Rao, D. Narayana; Kaskel, Stefan; Feng, Xinliang [Angewandte Chemie - International Edition, 2019, vol. 58, # 21, p. 6896 - 6900][Angew. Chem., 2019, vol. 131, # 21, p. 6970 - 6974,5]
[2]Samal, Mahalaxmi; Valligatla, Sreeramulu; Saad, Nabil A.; Rao, M. Veeramohan; Rao, D. Narayana; Sahu, Rojalin; Biswal, Bishnu P. [Chemical Communications, 2019, vol. 55, # 74, p. 11025 - 11028]
[3]Eder, Grace M.; Pyles, David A.; Wolfson, Eric R.; McGrier, Psaras L. [Chemical Communications, 2019, vol. 55, # 50, p. 7195 - 7198]

75
[ 29162-73-0 ]
[ 6147-53-1 ]
[ 178476-63-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	In N,N-dimethyl-formamide at 150℃; Inert atmosphere;

Reference： [1]Lv, Xuehui; Chen, Yanli; Wu, Yanling; Wang, Haoyuan; Wang, Xinlong; Wei, Chuangyu; Xiao, Zuoxu; Yang, Guangwu; Jiang, Jianzhuang [Journal of Materials Chemistry A, 2019, vol. 7, # 47, p. 27089 - 27098]

76
[ 29162-73-0 ]
[ 98-80-6 ]
[ 81566-83-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 24h;

Reference： [1]Gao, Hongshuai; Guan, Pengxin; Li, Zhiyong; Qiu, Jikuan; Wang, Huiyong; Wang, Jianji; Zhang, Hucheng; Zhang, Suojiang; Zhao, Yuling [Green Chemistry, 2020, vol. 22, # 8, p. 2605 - 2612]

77
[ 29162-73-0 ]
zinc acetate hydrate [ No CAS ]
[ 29116-34-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol; dichloromethane at 20℃; for 5h;

Reference： [1]Dechant, Moritz; Gerbig, Lisa; Ghosh, Tapas; Lambov, Martin; Lehmann, Matthias [Journal of Materials Chemistry C, 2020, vol. 8, # 16, p. 5562 - 5571]

78
[ 29162-73-0 ]
[ 87199-17-5 ]
C₇₂H₄₆N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 150℃; for 18h; Inert atmosphere;

Reference： [1]Achimas-Cadariu, Patriciu; Cristea, Castelia; Fischer-Fodor, Eva; Focsan, Monica; Gaina, Luiza; Gal, Emese; Molnar, Eva; Perde-Schrepler, Maria; Silaghi-Dumitrescu, Luminita [International Journal of Molecular Sciences, 2020, vol. 21, # 9]

79
[ 29162-73-0 ]
3-formyl-10-methyl-10H-phenothiazin-7-ylboronic acid pinacolate [ No CAS ]
5,10,15,20-tetrakis-[4-(3-formyl-10-methyl-10H-phenothiazin-7-yl)phenyl]-21,23H-porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 150℃; for 18h; Inert atmosphere;

Reference： [1]Achimas-Cadariu, Patriciu; Cristea, Castelia; Fischer-Fodor, Eva; Focsan, Monica; Gaina, Luiza; Gal, Emese; Molnar, Eva; Perde-Schrepler, Maria; Silaghi-Dumitrescu, Luminita [International Journal of Molecular Sciences, 2020, vol. 21, # 9]

80
[ 419536-33-7 ]
[ 29162-73-0 ]
C₁₁₆H₇₄N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 150℃; for 18h; Inert atmosphere;

Reference： [1]Achimas-Cadariu, Patriciu; Cristea, Castelia; Fischer-Fodor, Eva; Focsan, Monica; Gaina, Luiza; Gal, Emese; Molnar, Eva; Perde-Schrepler, Maria; Silaghi-Dumitrescu, Luminita [International Journal of Molecular Sciences, 2020, vol. 21, # 9]

81
[ 29162-73-0 ]
iron(III) chloride hexahydrate [ No CAS ]
5,10,15,20-tetra(4-bromophenyl)iron porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide for 6h; Reflux;	2 Synthesis of monomer 5,10,15,20-tetra(4-bromophenyl) iron porphyrin (FeTBrPP) In a 250mL three-necked flask, dissolve H2TBrPP (1mmol, 0.93g) in 150mL DMF, then add FeCl36H2O (5mmol, 1.35g), stir and heat to reflux for 6h. Then the solvent DMF was distilled off under reduced pressure. After cooling to room temperature, a large amount of water was added to wash, and FeCl3 was removed by filtration until the wash was colorless. At this time, the filter cake was purple, that is, the monomer 5,10,15,20-tetra(4) -Bromophenyl) iron porphyrin(FeTBrPP).

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN111559951, 2020, A Location in patent: Paragraph 0087; 0094-0095

82
[ 29162-73-0 ]
[W(≡CSnⁿBu₃)(CO)₂(hydrotris(3,5-dimethylpyrazol-1-yl)borate)] [ No CAS ]
C₁₁₆H₁₁₄B₄N₂₈O₈W₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro(dimethylsulfide) gold(I) In toluene for 14h; Inert atmosphere; Schlenk technique; Reflux;

Reference： [1]Frogley, Benjamin J.; Hill, Anthony F. [Dalton Transactions, 2020, vol. 49, # 35, p. 12390 - 12400]

83
[ 29162-73-0 ]
C₄₄H₂₂Br₄N₄Ni [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / 1 h / 140 °C 2: iron(III) chloride / dichloromethane; nitromethane / 48 h / 20 °C / Inert atmosphere

Reference： [1]Hampel, Frank; Jux, Norbert; Martin, Max M.; Oleszak, Christoph [European Journal of Organic Chemistry, 2020, vol. 2020, # 43, p. 6758 - 6762]

84
bis(acetylacetonate)nickel(II) [ No CAS ]
[ 29162-73-0 ]
[ 112592-50-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	In toluene at 140℃; for 1h;

Reference： [1]Hampel, Frank; Jux, Norbert; Martin, Max M.; Oleszak, Christoph [European Journal of Organic Chemistry, 2020, vol. 2020, # 43, p. 6758 - 6762]

85
[ 29162-73-0 ]
nickel dichloride [ No CAS ]
[ 122-52-1 ]
C₄₄H₃₂N₄NiO₁₂P₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 5,10,15,20-tetrakis(p-bromophenyl)porphyrin; nickel dichloride at 170℃; Inert atmosphere; Stage #2: triethyl phosphite at 170℃; for 24h; Inert atmosphere; Stage #3: With hydrogenchloride; water Inert atmosphere;

Reference： [1]Wang, Yijie; Yin, Jianbo; Liu, Di; Gao, Chengqi; Kang, Zixi; Wang, Rongming; Sun, Daofeng; Jiang, Jianzhuang [Journal of Materials Chemistry A, 2021, vol. 9, # 5, p. 2683 - 2688]

86
[ 29162-73-0 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 178476-63-6 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide for 12h; Reflux;	Synthesis of monometallic cobalt porphyrin General procedure: 5,10,15,20-tetrakis(4-bromophenyl)-21H,23H-porphyrin (TBPP)was synthesized firstly. The typical procedure: 18.5 g (0.1 mol) of pbromobenzaldehydedissolved in 120 mL of propionic acid and heatedto reflux, within 30 min dropwise addition of 30 mL of propionic acidsolution dissolved in 6.7 g (0.1 mol) of pyrrole. After refluxing for 0.5 h,it was cooled to room temperature and filtered with suction to obtain asolid, which was washed three times with 50 mL of methanol. Recrystallizedthree times with chloroform: methanol (15 mL:60 mL) and driedto obtain 5,101,520-tetrakis(4-bromophenyl)-21H,23H-porphyrin(TBPP) purple crystals. The product was characterized by 1HMR,UV-vis and FT-IR, and proved to be TBPP.Then 0.93 g (1 mmol) and 2.85 g CoCl2• 6H2O (12 mmol) of the obtainedTBPP placed in a round bottom flask, add 100 mL of DMF, andheat to reflux for 12 h. After cooling to room temperature, the precipitatewas precipitated by adding water and suction filtered. Afterwashing with water and methanol several times, it was vacuum dried at70 C for 8 h to obtain a red-brown cobalt porphyrin complex Co(II)(5,10,15,20-tetrakis(4-bromophenyl)-21H,23H-porphyrin) (CoTBPP).

Reference： [1]Tan, Mingyang; Zhu, Liang; Liu, Hao; Fu, Yajun; Yin, Shuang-Feng; Yang, Weijun [Applied Catalysis A: General, 2021, vol. 614]

87
[ 29162-73-0 ]
[ 6156-78-1 ]
C₄₄H₂₄Br₄MnN₄⁽¹⁺⁾*C₂H₃O₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In methanol; chloroform at 60℃; for 3h;

Reference： [1]Jiang, Lu; Chee, Pei Lin; Gao, Jian; Gan, Ching Ruey Raymond; Owh, Cally; Lakshminarayanan, Rajamani; Jiang, Shan; Hor, T. S. Andy; Loh, Xian Jun [Chemistry - An Asian Journal, 2021, vol. 16, # 8, p. 1007 - 1015]

88
[ 29162-73-0 ]
[ 6147-53-1 ]
C₄₄H₂₄Br₄CoN₄⁽¹⁺⁾*C₂H₃O₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In methanol; chloroform at 60℃; for 3h;

Reference： [1]Jiang, Lu; Chee, Pei Lin; Gao, Jian; Gan, Ching Ruey Raymond; Owh, Cally; Lakshminarayanan, Rajamani; Jiang, Shan; Hor, T. S. Andy; Loh, Xian Jun [Chemistry - An Asian Journal, 2021, vol. 16, # 8, p. 1007 - 1015]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	29162-73-0	MDL No. :	MFCD02114459
Formula :	C₄₄H₂₆Br₄N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ANWXWWSYNQLVED-UHFFFAOYSA-N
M.W :	930.32	Pubchem ID :	135412612
Synonyms :

Num. heavy atoms :	52
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 :	234.27
TPSA :	56.3 Å²

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) :	-2.62 cm/s

Log Po/w (iLOGP) :	6.95
Log Po/w (XLOGP3) :	13.17
Log Po/w (WLOGP) :	10.28
Log Po/w (MLOGP) :	7.01
Log Po/w (SILICOS-IT) :	12.83
Consensus Log Po/w :	10.05

[ CAS No. 29162-73-0 ] {[proInfo.proName]}

Quality Control of [ 29162-73-0 ]

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Calculated chemistry of [ 29162-73-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 29162-73-0 ]

Application In Synthesis of [ 29162-73-0 ]

[ 29162-73-0 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	2.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	3.0
Bioavailability Score :	0.17

Log S (ESOL) :	-14.12
Solubility :	0.0 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (Ali) :	-14.4
Solubility :	0.0 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-18.36
Solubility :	4.07e-16 mg/ml ; 4.38e-19 mol/l
Class :	Insoluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	7.45

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Prevention
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P222	Do not allow contact with air.
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P234	Keep only in original container.
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Code	Phrase
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P352	Wash with plenty of soap and water.
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P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
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