(2.2)Paracyclophane

Chemical compound From Wikipedia, the free encyclopedia

[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.[4]

Quick facts Names, Identifiers ...
(2.2)Paracyclophane
Names
Preferred IUPAC name
1,4(1,4)-Dibenzenacyclohexaphane[1]
Other names
[2.2](1,4)Cyclophane
1,4-Carbophane
Cyclobis(benzene-1,4-dimethylene)
Parylene dimer
Di-p-xylylene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.132 Edit this at Wikidata
EC Number
  • 216-644-2
  • InChI=1S/C16H16/c1-2-14-4-3-13(1)9-10-15-5-7-16(8-6-15)12-11-14/h1-8H,9-12H2
    Key: OOLUVSIJOMLOCB-UHFFFAOYSA-N
  • C=1C=C2C=CC1CCC3=CC=C(C=C3)CC2
Properties
C16H16
Molar mass 208.304 g·mol−1
Appearance White solid[2]
Density 1.242 g/cm3 (260 K)[3]
Melting point 285 °C (545 °F; 558 K)[4]
Hazards
GHS labelling:[5]
GHS07: Exclamation markGHS08: Health hazard
Warning
H317, H373
P260, 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).
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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.[6]

References

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