ChemicalBook CAS DataBase List meso-Tetra(4-carboxyphenyl)porphine

meso-Tetra(4-carboxyphenyl)porphine synthesis

9synthesis methods

Product Name:meso-Tetra(4-carboxyphenyl)porphine
CAS Number:14609-54-2
Molecular formula:C48H30N4O8
Molecular Weight:790.77

General procedures for the synthesis of porphyrins 1-5A mixture of the appropriate aromatic aldehyde (0.72 mmol) andpyrrole (0.72 mmol) in DMF (15 mL) was placed into a 50 mL threeneckedflask. The mixture was flushed with nitrogen gas for a coupleof minutes and then heated to 100 C for 10 min. P-toluene sulphonicacid (0.72 mmol, dissolved in DMF) was then added to the reactionmixture. The colorless mixture turned red over the next couple of minutesthen heated at 150 C for 1 h. The reaction mixture was thencooled and poured over ice with stirring for 15 min the residue wascollected, dried under vacuum and purified by column chromatographyusing chloroform/hexane (1.5/1) as eluent).

MESO-TETRA(4-CARBOXYPHENYL)PORPHINE TETRAMETHYL ESTER

22112-83-0
88 suppliers
$24.00/250mg

14609-54-2
206 suppliers
$9.00/100mg

Yield:14609-54-2 98%

Reaction Conditions:

with potassium hydroxide in tetrahydrofuran;water at 75; for 16 h;

Steps:

2.3. Synthesis of tetra- and octaacid substituted porphyrins

General procedure: Tetramethylester (0.593 g, 0.70 mmol) or octaethylesterporphyrin (0.834 g, 0.70 mmol) was dissolved in 100 mL THF in atwo neck round bottom flask. To this, 10 mL of aq. solution of KOH(300 equivalents) was added and refluxed for 16 h at 75 °C. Aftercompletion of the reaction, THF was removed using rotary evaporatorand the resulting residue was treated with 2N HCl (150 mL)which resulted green precipitate, filtered and washed with water(50 mL x 5). The protonated porphyrin was neutralized with pyridine(15 mL). Then, the pyridine was removed by rotary evaporationand the resulting residue was washed with water (50 mL x 3)and dried under vacuum. The crude porphyrin was recrystallizedfrom CHCl3 and acetone mixture (3:7, v/v). The yield was found tobe 0.54 g (98%) for the corresponding tetraacid and 0.680 g (100%)for octaacid.

References:

Yadav, Pinky;Sankar, Muniappan [Dyes and Pigments,2017,vol. 139,p. 651 - 657]

109-97-7 Synthesis