Bilane

In organic chemistry, bilane is a compound with the formula C19H20N4 or [(C4H4N)−CH2−(C4H3N)−]2CH2. It is a tetrapyrrole, a class of compounds with four independent pyrrole rings. Specifically, the molecule can be described as four pyrrole molecules C4H5N connected in an open chain by three methylene bridges −CH2− at carbons adjacent to the nitrogens, replacing the respective hydrogens.

Bilane
Names
IUPAC name
5,10,15,22,23,24-Hexahydro-21H-biline
Systematic IUPAC name
11H,31H,51H,71H-1,7(2),3,5(2,5)-Tetrapyrrolaheptaphane
Other names
Bilinogen; Tetrapyrrolotrismethane
Identifiers
3D model (JSmol)
8008279
ChEBI
ChemSpider
  • InChI=1S/C19H20N4/c1-3-14(20-9-1)11-16-5-7-18(22-16)13-19-8-6-17(23-19)12-15-4-2-10-21-15/h1-10,20-23H,11-13H2
    Key: AXMKEYXDFDKKIO-UHFFFAOYSA-N
  • C1=CNC(=C1)CC2=CC=C(N2)CC3=CC=C(N3)CC4=CC=CN4
Properties
C19H20N4
Molar mass 304.397 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

The name is also used for the class of compounds formally derived from bilane proper by replacement of some additional hydrogen atoms by various functional groups. Natural bilanes usually have side chains substituted on the two carbons in each pyrrole ring that are not adjacent to the nitrogens. Artificial bilanes may be substituted on the bridging carbons (called meso positions).

The parent (unsubstituted) bilane is difficult to prepare and unstable, but substituted derivatives are synthesized by most living organisms as intermediates in the synthesis of natural porphyrins. Substituted bilanes may also be the starting point for the synthesis of artificial porphyrins.

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