(2.2)Paracyclophane

(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 ;
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
Density	1.242 g/cm3 (260 K)
Melting point	285 °C (545 °F; 558 K)
Hazards
	GHS labelling:
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

[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]

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]

References

^ 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.
^ 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. doi:10.1002/chem.201304972. PMID 24740648.
^ ^a ^b 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.
^ "[2.2]Paracyclophane". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2023-11-24. Retrieved 2023-11-24.
^ 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. doi:10.1002/anie.201904863. PMC 7003812. PMID 31283092.

[1] 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.

[2] 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. doi:10.1002/chem.201304972. PMID 24740648.

[nature-3] 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.

[4] "[2.2]Paracyclophane". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2023-11-24. Retrieved 2023-11-24.

[5] 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. doi:10.1002/anie.201904863. PMC 7003812. PMID 31283092.

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