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5-(4-methoxyphenyl)dipyrromethane (CAS 176446-62-1)

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Alternate Names:
2-[(4-methoxyphenyl)-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
Application:
5-(4-methoxyphenyl)dipyrromethane is a pyrrole for building porphyrins
CAS Number:
176446-62-1
Molecular Weight:
252.31
Molecular Formula:
C16H16N2O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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5-(4-methoxyphenyl)dipyrromethane is a pyrrole building block for the synthesis of porphyrins. It consists of a pyrrole ring and two phenyl groups, forming a five-membered heterocyclic hydrocarbon. This valuable reagent plays a role in the creation of heterocyclic compounds and organic dyes. It proves instrumental in the synthesis of various organic compounds, including polymers and dyes. Moreover, it serves as a building block for the development of organic catalysts and catalytic materials. The mechanism of action of 5-(4-methoxyphenyl)dipyrromethane involves the condensation of 4-methoxyphenol and pyrrole. This reaction takes place in an aqueous acetic acid solution at a temperature of 80°C. Remarkably, this process yields a remarkable 88% of the desired product, 5-(4-methoxyphenyl)dipyrromethane.


5-(4-methoxyphenyl)dipyrromethane (CAS 176446-62-1) References

  1. Efficient synthesis of meso-substituted corroles in a H2O-MeOH mixture.  |  Koszarna, B. and Gryko, DT. 2006. J Org Chem. 71: 3707-17. PMID: 16674040
  2. A new synthesis of porphyrins via a putative trans-manganese(iv)-dihydroxide intermediate.  |  Mondal, S., et al. 2020. Dalton Trans. 49: 1424-1432. PMID: 31915769
  3. Synthesis and Structure of [meso-Triarylcorrolato]silver(III)  |  Christian Brückner, Cheri A. Barta, Raymond P. Briñas, and Jeanette A. Krause Bauer. 2003. Inorg. Chem. 42: 1673–1680.
  4. Effects of aldehyde or dipyrromethane substituents on the reaction course leading to meso-substituted porphyrins  |  G. Richard Geier III †, Jonathan S. Lindsey. 2004. Tetrahedron. 60: 11435-11444.
  5. Efficient and versatile single pot approach to dipyrromethanes and bis(heterocyclyl)methanes  |  Kamaljit Singh, Sonia Behal, Maninder Singh Hundal †. 2005. Tetrahedron. 61: 6614-6622.
  6. Synthesis of meso-substituted dipyrromethanes using iodine-catalysis  |  Pierre-Antoine Faugeras, Benjamin Boëns, Pierre-Henri Elchinger, Julien Vergnaud, Karine Teste, Rachida Zerrouki. 2010. Tetrahedron Letters. 51: 4630-4632.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

5-(4-methoxyphenyl)dipyrromethane, 1 g

sc-396885
1 g
$245.00

5-(4-methoxyphenyl)dipyrromethane, 5 g

sc-396885A
5 g
$979.00