2,5-Bis(hydroxymethyl)pyrrole

2,5-Bis(hydroxymethyl)pyrrole
Names
	Preferred IUPAC name (1H-Pyrrole-2,5-diyl)dimethanol
Identifiers
CAS Number	6249-04-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	4324991;
PubChem CID	5151810;
UNII	T54C5XUX7E ;
CompTox Dashboard (EPA)	DTXSID00408880 ;
	InChI Key: INNRTGSPTOTXLK-UHFFFAOYSA-N; InChI=1S/C6H9NO2/c8-3-5-1-2-6(4-9)7-5/h1-2,7-9H,3-4H2;
	SMILES C1=C(NC(=C1)CO)CO;
Properties
Chemical formula	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). Infobox references

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]

References

^ ^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.

[tani-1] 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.

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