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.^[1]

Quick facts Names, Identifiers ...

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
CAS Number	68277-11-2
3D model (JSmol)	Interactive image
Beilstein Reference	8008279
ChEBI	CHEBI:36305
ChemSpider	7827700
PubChem CID	9548777
CompTox Dashboard (EPA)	DTXSID401336226
InChI 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
SMILES C1=CNC(=C1)CC2=CC=C(N2)CC3=CC=C(N3)CC4=CC=CN4
Properties
Chemical formula	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

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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).^[2]

The parent (unsubstituted) bilane is difficult to prepare and unstable,^[3] 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.^[2][3]