Triptycene

Triptycene

Identifiers
CAS Number	477-75-8 Y
3D model (Jmol)	Interactive image
ChemSpider	83742
ECHA InfoCard	100.006.837
EC Number	207-519-3
PubChem	92764
InChI InChI=1S/C20H14/c1-2-8-14-13(7-1)19-15-9-3-5-11-17(15)20(14)18-12-6-4-10-16(18)19/h1-12,19-20H Key: NGDCLPXRKSWRPY-UHFFFAOYSA-N
SMILES C12=CC=CC=C1C3C5=C(C=CC=C5)C2C4=C3C=CC=C4
Properties
Chemical formula	C20H14
Molar mass	254.33 g·mol−1
Melting point	252 to 256 °C (486 to 493 °F; 525 to 529 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Triptycene is an aromatic hydrocarbon, the simplest iptycene molecule with the formula C₂H₂(C₆H₄)₃. It is a white solid that is soluble in organic solvents. The compound has a paddlewheel configuration with D_3hsymmetry. Several substituted triptycenes are known. Barrelenes are structurally related.

The parent triptycene was first prepared in 1942 by a multistep method. It can also be prepared in one step in moderate yields (28%) from the Diels-Alder reaction of anthracene and benzyne. In this method, benzyne is generated by the reaction of magnesium in the presence of 2-bromofluorobenzene.

The hydrocarbon framework is very rigid and triptycene and triptycene derivatives such as triptycene quinones are therefore incorporated in many organic compounds as a molecular scaffold for instance in molecular motors or as a ligand for example in this hydrocyanation:

In this reaction the substrate is butadiene, the reagent acetonecyanohydrine, the catalyst Ni(cod)₂ and the ligand a bidentate organophosphine with a large bite angle on a triptycene scaffold.