2,5-Bis(hydroxymethyl)pyrrole

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2,5-Bis(hydroxymethyl)pyrrole
2,5-bis(hydroxymethyl)pyrrole.svg
Names
Preferred IUPAC name
(1H-Pyrrole-2,5-diyl)dimethanol
Identifiers
3D model (JSmol)
UNII
  • Key: INNRTGSPTOTXLK-UHFFFAOYSA-N
  • InChI=1S/C6H9NO2/c8-3-5-1-2-6(4-9)7-5/h1-2,7-9H,3-4H2
  • C1=C(NC(=C1)CO)CO
Properties
C6H9NO2
Molar mass 127.143 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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−CH2 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.[1] The compound was used as an intermediate in the synthesis of hexahydroporphine ("unsubstituted porphyrinogen"),[1] the core of uroporphyrinogen III, precursor of many critically important biological products such as hemoglobin and chlorophyll.

Preparation[edit]

The compound can be synthesized by formylation of pyrrole followed by reduction of the resulting pyrrolecarboxaldehyde.[1]

References[edit]

  1. ^ a b c Taniguchi, Shozo; Hasegawa, Hikaru; Yanagiya, Shoko; Tabeta, Yusuke; Nakano, Yoshiharu; Takahashi, Masahiko (2001). "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. doi:10.1016/S0040-4020(01)00059-X.