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)
ChemSpider
PubChem CID
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

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

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<span class="mw-page-title-main">Arsole</span> Chemical compound

Arsole, also called arsenole or arsacyclopentadiene, is an organoarsenic compound with the formula C4H5As. It is classified as a metallole and is isoelectronic to and related to pyrrole except that an arsenic atom is substituted for the nitrogen atom. Whereas the pyrrole molecule is planar, the arsole molecule is not, and the hydrogen atom bonded to arsenic extends out of the molecular plane. Arsole is only moderately aromatic, with about 40% the aromaticity of pyrrole. Arsole itself has not been reported in pure form, but several substituted analogs called arsoles exist. Arsoles and more complex arsole derivatives have similar structure and chemical properties to those of phosphole derivatives. When arsole is fused to a benzene ring, this molecule is called arsindole, or benzarsole.

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4
H
4
PH
; it is the phosphorus analog of pyrrole. The term phosphole also refers to substituted derivatives of the parent heterocycle. These compounds are of theoretical interest but also serve as ligands for transition metals and as precursors to more complex organophosphorus compounds.

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Uroporphyrinogen III is a tetrapyrrole, the first macrocyclic intermediate in the biosynthesis of heme, chlorophyll, vitamin B12, and siroheme. It is a colorless compound, like other porphyrinogens.

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H
7
BN
2
F
2
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2
joined to a dipyrromethene group C
9
H
7
N
2
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<span class="mw-page-title-main">Stibole</span> Chemical compound

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<span class="mw-page-title-main">Bismole</span> Chemical compound

Bismole is a theoretical heterocyclic organic compound, a five-membered ring with the formula C4H4BiH. It is classified as a metallole. It can be viewed as a structural analog of pyrrole, with bismuth replacing the nitrogen atom of pyrrole. The unsubstituted compound has not been isolated due to the high energy of the Bi-H bond. Substituted derivatives, which have been synthesized, are called bismoles.

The molecular formula C6H9NO2 (molar mass: 127.14 g/mol, exact mass: 127.0633 u) may refer to:

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9
H
8
N
2
whose skeleton can be described as two pyrrole rings C
5
N
connected by a methyne bridge =CH– through their nitrogen-adjacent (position-2) carbons; the remaining bonds being satisfied by hydrogen atoms. It is an unstable compound that is readily attacked by nucleophilic compounds above −40 °C.

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Phosphorus-centered porphyrins are conjugated polycyclic ring systems consisting of either four pyrroles with inward-facing nitrogens and a phosphorus atom at their core or porphyrins with one of the four pyrroles substituted for a phosphole. Unmodified porphyrins are composed of pyrroles and linked by unsaturated hydrocarbon bridges often acting as multidentate ligands centered around a transition metal like Cu II, Zn II, Co II, Fe III. Being highly conjugated molecules with many accessible energy levels, porphyrins are used in biological systems to perform light-energy conversion and modified synthetically to perform similar functions as a photoswitch or catalytic electron carriers. Phosphorus III and V ions are much smaller than the typical metal centers and bestow distinct photochemical properties unto the porphyrin. Similar compounds with other pnictogen cores or different polycyclic rings coordinated to phosphorus result in other changes to the porphyrin’s chemistry.

References

  1. 1 2 3 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.