(2.2)Paracyclophane

(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
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
InChI 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
SMILES C=1C=C2C=CC1CCC3=CC=C(C=C3)CC2
Properties
Chemical formula	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]
Pictograms
Signal word	Warning
Hazard statements	H317, H373
Precautionary statements	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). Infobox references

[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]

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

1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. P-26.4.1.4. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
2. Pan, Donghui; Wang, Yanbin; Xiao, Guomin (2016). "A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane". Beilstein Journal of Organic Chemistry. 12: 2443–2449. doi:10.3762/bjoc.12.237. PMC   5238561 . PMID   28144311.
3. Wolf, Hilke; Leusser, Dirk; Jørgensen, Mads R. V.; Herbst-Irmer, Regine; Chen, Yu-Sheng; Scheidt, Ernst-Wilhelm; Scherer, Wolfgang; Iversen, Bo B.; Stalke, Dietmar (2014). "Phase Transition of [2,2]-Paracyclophane – an End to an Apparently Endless Story". Chemistry – A European Journal. 20 (23): 7048–7053. Bibcode:2014ChEuJ..20.7048W. doi:10.1002/chem.201304972. PMID   24740648.
4. Brown, C. J.; Farthing, A. C. (1949). "Preparation and Structure of Di-p-Xylylene". Nature. 164 (4178): 915–916. Bibcode:1949Natur.164R.915B. doi:10.1038/164915b0. S2CID   4132106.
5. "[2.2]Paracyclophane". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2023-11-24. Retrieved 2023-11-24.
6. Hassan, Zahid; Spuling, Eduard; Knoll, Daniel M.; Bräse, Stefan (2020). "Regioselective Functionalization of [2.2]Paracyclophanes: Recent Synthetic Progress and Perspectives". Angewandte Chemie International Edition. 59 (6): 2156–2170. Bibcode:2020ACIE...59.2156H. doi:10.1002/anie.201904863. PMC   7003812 . PMID   31283092.