(2.2)Paracyclophane

[2.2]Paracyclophane is a cyclophane that is applied in bio- and materials science. It was first synthesized by Brown and Farthing in 1949 by pyrolyzing para-xylene in the gas phase under low pressure.^[3]

(2.2)Paracyclophane

Names
IUPAC name Tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene
Other names [2.2](1,4)Cyclophane 1,4-Carbophane Cyclobis(benzene-1,4-dimethylene) Parylene dimer Di-p-xylylene
Identifiers
CAS Number	1633-22-3 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3278516
ChemSpider	66818
ECHA InfoCard	100.015.132
EC Number	216-644-2
PubChem CID	74210
CompTox Dashboard (EPA)	DTXSID9061835
SMILES C=1C=C2C=CC1CCC3=CC=C(C=C3)CC2
Properties
Chemical formula	C16H16
Molar mass	208.304 g·mol−1
Appearance	White solid[1]
Density	1.242 g/cm3 (260 K)[2]
Melting point	285 °C (545 °F; 558 K)[3]
Hazards
GHS labelling:[4]
Pictograms
Signal word	Warning
Hazard statements	H317, H373
Precautionary statements	P260, P261, P272, P280, P302+P352, P319, P321, P333+P317, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Reactions

[2.2]Paracyclophane is stable under normal conditions. Its formyl, acetyl, nitro- and bromo- derivatives can be obtained by electrophilic aromatic substitution in one step.^[5]