Porphyrin Building Blocks

Numerous methods are utilized to synthesize porphyrins, depending on the target porphyrin structure and symmetry; selection of porphyrin building blocks are key for an efficient successful synthesis. The condensation of pyrroles with aldehydes and subsequent oxidation is the most widely used methodology for porphyrin synthesis. Substitution resulting from this methodology is limited to symmetric porphyrins due to the use of identically substituted pyrroles. Several other approaches are also used to synthesize complex asymmetrically substituted porphyrins. These methodologies include the 2+2 MacDonald cyclization and Fischer porphyrin synthesis which proceed by the condensation of two dipyrrolemethene building blocks. Condensation of an α-tripyrrole with a 2,5-diformylpyrrole using a 3+1 approach and cyclization of open chain tetrapyrroles such as b-bilenes and a,c-biladienes can also be used to synthesize highly functionalized asymmetric porphyrins.

Many highly functionalized porphyrinoid compounds can be synthesized by synthetic modification of natural porphyrin derivatives such as chlorophyll and heme.

Frontier Specialty Chemicals offers numerous building blocks for the synthesis of novel porphyrins and related compounds.

Substituted pyrrole building blocks available from Frontier Scientific

Catalog Number: PB1983Catalog Number: E15130Catalog Number: E15129Catalog Number: PB1985

Catalog Number: T1927Catalog Number: E15002Catalog Number: PB10186Catalog Number: P12623

Specific synthetic examples using substituted pyrroles available from Frontier Scientific

Catalog Number: E15129

Ivanova, Y.B., Mamardashvili, N.Z., Glazunov, A.V. et al, Russ J Gen Chem. 85, 640–647, 2015

Catalog Number: P12623

Guilard, R. et al, Synthesis, (12), 1480-2; 1995

Catalog Number: T1927

Sugiura, Ken-ichi et al, Journal of Materials Chemistry, 10 (11), 2507-2514; 2000


Catalog Number: PB1987Catalog Number: PB1988Catalog Number: PB12066Catalog Number: PB12065
Catalog Number: PB12171Catalog Number: PB12760Catalog Number: PB13620Catalog Number: PB1978Catalog Number:
Catalog Number: PB1980Catalog Number: PB1981Catalog Number: PB1986Catalog Number: PB1982

Specific Synthetic examples of the use of dipyrromethanes in porphyrin synthesis

Catalog Number: PB12171

Malatesti, Nela et al, International Journal of Oncology, 28 (6), 1561-1569; 2006

Catalog Number: PB1988

Nagpal, Ritika et al, ChemistrySelect, 4 (29), 8444-8449; 2019


Porphyrins which are asymmetric and have a different substituents at the β positions can be synthesized using cyclization of open chain tetrapyrroles. Oxidative cyclization of linear tetrapyrroles using transition metals gives the desired porphyrin.

Catalog Number: M14136
Catalog Number: P14137
Catalog Number: B610-9
Biliverdin Dimethyl Ester

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