Octaethylporphyrin

Octaethylporphyrin

Names
Other names 2,3,7,8,12,13,17,18-Octaethyl-21H,23H-porphine
Identifiers
CAS Number	2683-82-1
3D model (JSmol)	Interactive image
Beilstein Reference	379798
ChEBI	CHEBI:52183
ChemSpider	10445887
EC Number	220-243-8
PubChem CID	102311
UNII	PD85YF7CEP Y
CompTox Dashboard (EPA)	DTXSID2062589
InChI InChI=1S/C36H46N4/c1-9-21-22(10-2)30-18-32-25(13-5)26(14-6)34(39-32)20-36-28(16-8)27(15-7)35(40-36)19-33-24(12-4)23(11-3)31(38-33)17-29(21)37-30/h17-20,37,40H,9-16H2,1-8H3/b29-17-,30-18-,31-17-,32-18-,33-19-,34-20-,35-19-,36-20- Key: HCIIFBHDBOCSAF-MUZKIALCSA-N
SMILES CCC1=C(C2=CC3=NC(=CC4=C(C(=C(N4)C=C5C(=C(C(=N5)C=C1N2)CC)CC)CC)CC)C(=C3CC)CC)CC
Properties
Chemical formula	C36H46N4
Molar mass	534.792 g·mol−1
Appearance	purple solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Octaethylporphyrin (H₂OEP) is an organic compound that is a relative of naturally occurring heme pigments. The compound is used in the preparation of models for the prosthetic group in heme proteins. It is a dark purple solid that is soluble in organic solvents. As its conjugate base OEP^2-, it forms a range of transition metal porphyrin complexes. When treated with ferric chloride in hot acetic acid solution, it gives the square pyramidal complex Fe(OEP)Cl. It also forms the square planar complexes Ni(OEP) and Cu(OEP).

Saturated solution of H₂OEP in dichloromethane.

Contrast with other porphyrins

Unlike complexes of the naturally occurring porphyrins, OEP complexes have four-fold symmetry, which simplifies spectroscopic analysis. In contrast to tetraphenylporphyrin and related analogues, H₂OEP features unprotected meso positions. In this way, it is a more accurate model for naturally occurring porphyrins.

Synthesis

H₂OEP is prepared by condensation of 3,4-diethylpyrrole with formaldehyde.