2,5-Bis(hydroxymethyl)pyrrole

2,5-bis(hydroxymethyl)pyrrole.svg 180px (1H-Pyrrole-2,5-diyl)dimethanol 6249-04-3 correct CAS 4324991 correct FDA T54C5XUX7E 5151810 1S/C6H9NO2/c8-3-5-1-2-6(4-9)7-5/h1-2,7-9H,3-4H2 INNRTGSPTOTXLK-UHFFFAOYSA-N C1=C(NC(=C1)CO)CO 6 9 1 2 2,5-Bis(hydroxymethyl)pyrrole is an organic chemical compound with formula C6H9O2N, or (HOCH2)2(C4H3N). Its molecule can be described as that of pyrrole C4H5N with hydroxymethyl groups HO\sCH2\s replacing the two hydrogen atoms adjacent to the nitrogen atom. The compound is a white solid, soluble in water and acetone. It is stable in alkaline solutions, but otherwise tends to polymerize by self-condensation. The compound was used as an intermediate in the synthesis of hexahydroporphine ("unsubstituted porphyrinogen"), the core of uroporphyrinogen III, precursor of many critically important biological products such as hemoglobin and chlorophyll. Preparation The compound can be synthesized by formylation of pyrrole followed by reduction of the resulting pyrrolecarboxaldehyde. 10.1016/S0040-4020(01)00059-X The first isolation of unsubstituted porphyrinogen and unsubstituted 21-oxaporphyrinogen by the '3+1' approach from 2,5-bis(hydroxymethyl)pyrrole and tripyrrane derivatives Tetrahedron 57 11 2103–2108 2001 Taniguchi Shozo Hasegawa Hikaru Yanagiya Shoko Tabeta Yusuke Nakano Yoshiharu Takahashi Masahiko References Category:Pyrroles Category:Diols