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[ CAS No. 160240-15-3 ]

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Chemical Structure| 160240-15-3
Chemical Structure| 160240-15-3
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Product Details of [ 160240-15-3 ]

CAS No. :160240-15-3 MDL No. :MFCD31700791
Formula : C52H30N4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :710.82 g/mol Pubchem ID :-
Synonyms :

Safety of [ 160240-15-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 160240-15-3 ]

  • Downstream synthetic route of [ 160240-15-3 ]

[ 160240-15-3 ] Synthesis Path-Downstream   1~7

  • 1
  • 5,10,15,20-tetrakis-(4-[(trimethylsilyl)ethynyl]phenyl)porphyrin [ No CAS ]
  • [ 160240-15-3 ]
YieldReaction ConditionsOperation in experiment
With tetrabutyl ammonium fluoride In tetrahydrofuran; chloroform at -30 - 50℃; for 20h; Cooling with liquid nitrogen-acetone bath; 2.2 2) Synthesis of tetrakis(4-ethynylphenyl)porphyrin (TEPP) (2) A solution of 700 mg (0.7 mmol) of protected TEPP (1) obtained above in 500 ml of a chloroform/tetrahydrofuran (THF) mixture (1/1 v/v) was cooled in a bath of liquid nitrogen and acetone to a temperature of between -30 and -50° C., and then a 1 mol/l solution of tetrabutylammonium fluoride (TBAF) in THF (259 mg, 0.99 mmol in 1 ml) was added to the reaction mixture, which was subsequently stirred for 20 hours. The rise in temperature was not controlled. The solvent was subsequently evaporated off and the deprotected porphyrin (2) was obtained in the form of a purple powder (747 mg, 1.05 mmol).
With tetrabutyl ammonium fluoride In tetrahydrofuran; chloroform at 25℃; for 24h; Inert atmosphere;
With tetrabutyl ammonium fluoride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Preparation of 5,10,15,20-tetra(4-ethynylphenyl)porphyrin monomer reactant 4.63g (5mmol) p-bromobenzaldehyde was added to the tetrahydrofuran and triethylamine mixed solution (3: 1, v / v), Stirred vigorously for 30 minutes under nitrogen protection. Afterwards, add 190mg(1.0mmol) cuprous iodide and 350mg bistriphenylphosphine palladium dichloride(0.5mmol). After 10 minutes, slowly add dropwise over 1 hour 3.7mL (26.3mmol) of trimethylsilyl acetylene. React for 3 hours. After completion of the reaction, diluted with ethylacetate, washed three times with saturated brine, then dried over anhydrousmagnesium sulfate. Spin-dry product after the oily solvent, and then purifiedby a silica gel column, eluent used petroleum ether: ethyl acetate = 20: 1 togive the pure compound 4-trimethylsilyl ethynylbenzaldehyde. 752 mg 4-trimethylsilyl ethynylbenzaldehyde dissolved in 100mL of chloroform, stirred under nitrogen for 30 minutes uniformly. By using a pipette, 275mg pyrrole was added, then add 116μL boron trifluoride etherate. At room temperature react for1.5 ~ 2 hours, until the 4-trimethylsilyl ethynylbenzaldehyde reacted completely.After addition of 0.64g2,3- dichloro-5,6-dicyano-1,4-benzoquinone and reacting for0.5 hours, the reaction was added 126μL of triethylamine and reacted for 10 minutes.The reaction solution was added directly to a silica gel column with chloroformas an eluent until no red liquid effluent, after which spin dry, dissolved inmethanol and washing, filtration to give a purple solid tetrakis(trimethylsilyl ethynyl) porphyrin. At -78 deg.C, solution containing 43.6 milligrams (mg)(0.066 millimoles (mmol)) 5,10,15,20- tetrakis (trimethylsilyl ethynyl)porphyrin in tetrahydrofuran (THF) was added 0.4ml tetrabutylammonium fluoride(TBAF) (1 mol / l (M) in tetrahydrofuran, 0.4mmol), the reaction mixture wasstirred under nitrogen for 1.5 hours, until the reaction was complete tracking gussets. The reaction was purified by silica gel column, to give removed trimethylsilylacetylenegroup 5,10,15,20-tetra(4-ethynyl-phenyl) porphyrin monomer.
  • 2
  • [ 160240-15-3 ]
  • [ 935510-22-8 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 5,10,15,20-tetra(4-ethynylphenyl)porphyrin With iron(III) chloride In N,N-dimethyl-formamide for 24h; Heating / reflux; Stage #2: With 2,6-dimethylpyridine In N,N-dimethyl-formamide for 48h; Heating / reflux; 2.3 3) Synthesis of iron tetrakis(4-ethynylphenyl)porphyrin (FeCl-TEPP) (3) A solution of FeCl3.4H2O (4.56 g; 28.13 mmol) in DMF (100 ml) was added portionwise to a solution of 1 g (1.4 mmol) of porphyrin TEPP (2), as obtained above in the preceding step, in 400 ml of DMF and the whole was refluxed for 24 hours. 10 ml of 2,6-lutidine were then added, and the reflux was taken up again for 48 hours. The heating was stopped and the solvent was evaporated off under reduced pressure. The residue was taken up in 50 ml of water and stirred in order to eliminate a maximum of salts and of TBAF, and then filtered through paper. The residue was dissolved in 100 ml of chloroform and the organic phase was washed with a saturated aqueous solution of sodium chloride (3×100 ml) in order to be sure that the axial ligand of the iron is a chlorine atom. The organic phase was subsequently dried over sodium sulfate and the solvent was evaporated off. The iron tetrakis(4-ethynylphenyl)porphyrin (FeCl-TEPP) (3) (813 mg; 1.02 mmol; yield: 73%) was obtained in the form of a powder that was purple/black in color, and brown in solution in chloroform.
  • 3
  • [ 160240-15-3 ]
  • [ 935510-23-9 ]
YieldReaction ConditionsOperation in experiment
65% With cobalt(II) acetate In N,N-dimethyl-formamide for 20h; Heating / reflux; 2.4 4) Synthesis of cobalt tetrakis(4-ethynylphenyl)porphyrin (Co-TEPP) (4) A solution of 8.71 g (35 mmol) of cobalt acetate tetrahydrate (Co(CH3COO)2.4H2O) in 100 ml of DMF was added portionwise to a solution of 1.7 g (2.39 mmol) of porphyrin TEPP (2) as obtained above in step 2), in 500 ml of DMF. The mixture obtained was refluxed for 20 hours. The heating was stopped and 150 ml of water were added to the reaction medium. The mixture was subsequently extracted with ethanol (4×200 ml) and the organic phase was then evaporated. The residue was dissolved in 300 ml of ethanol, and the organic phase was washed with 3×200 ml of water and dried over sodium sulfate. The solvent was evaporated off and the cobalt tetrakis(4-ethynylphenyl)porphyrin (Co-TEPP) (4) (1.19 g; 1.55 mmol; yield: 65%) was obtained in the form of a powder that was purple/black in color, and red in solution in chloroform.
  • 4
  • [ 160240-15-3 ]
  • [ 935510-24-0 ]
YieldReaction ConditionsOperation in experiment
63% With manganese(ll) chloride In N,N-dimethyl-formamide for 72h; Heating / reflux; 2.5 5) Synthesis of Manganese tetrakis(4-ethynylphenyl)porphyrin (MnCl-TEPP) (5) A solution of 5.5 g (27.8 mmol) of manganese chloride tetrahydrate (MnCl2.4H2O) in 160 ml of DMF was added portionwise to a solution of 1 g (1.4 mmol) of porphyrin TEPP (2) as obtained in step 2) above and dissolved in 200 ml of DMF. The mixture was refluxed for 72 hours. After a return to ambient temperature, the solvent was evaporated off under reduced pressure. The residue was taken up in 50 ml of chloroform and the manganese salts were eliminated by filtration over celite. The liquid filtrate was evaporated and the residue was subsequently dissolved in 100 ml of ethanol and washed with 3×100 ml of water in order to eliminate the TBAF. After evaporation, the residue was dissolved in chloroform and this organic phase was in turn washed with a saturated aqueous solution of sodium chloride (3×100 ml) in order to be sure that the axial ligand of the manganese is a chlorine, and finally washed with 2×100 ml of water in order to eliminate the traces of sodium chloride. The organic phase was subsequently dried over sodium sulfate and the solvent was evaporated off. During the first extraction with ethanol and water as solvents, a part of the porphyrin precipitated. This precipitate was filtered off and kept. It was subsequently redissolved in chloroform so that it could be added to the organic phase during the washing with sodium chloride. 700 mg (0.88 mmol; yield 63%) of manganese tetrakis(4-ethynylphenyl)porphyrin (MnCl-TEPP) (5) were obtained in the form of a purple/black-colored powder which is green in solution in chloroform.
  • 5
  • [ 160240-15-3 ]
  • [ 502613-00-5 ]
YieldReaction ConditionsOperation in experiment
With zinc diacetate; triethylamine In methanol; dichloromethane for 16h; Reflux; Inert atmosphere;
  • 6
  • [ 77123-57-0 ]
  • [ 160240-15-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: propionic acid / 3 h / Reflux; Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran; chloroform / 24 h / 25 °C / Inert atmosphere
  • 7
  • [ 1122-91-4 ]
  • [ 160240-15-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0.17 h 1.3: 4 h 2.1: boron trifluoride diethyl etherate / chloroform / 20 °C / Inert atmosphere 2.2: 0.5 h 2.3: 0.17 h 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
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