| Identification | Back Directory | [Name]
[2.2]Paracyclophane | [CAS]
1633-22-3 | [Synonyms]
PCF
DI-P-XYLENE
PLANYLENE N
Paracyclophan
DI-P-XYLYLENE
Paracyclophane
Parylene N ,99%
Di-1,4-xylylene
Dimer,Parylene N
DI-PARA-XYLYLENE
[2.2]paracylophan
[2.2]PARACYCLOPHAN
[2.2]Paracylophane
Dicyclo-p-xylylene
TwodiMericp-xylene
[2.2]PARACYCLOPHANE
[2.2](1,4)Cyclophane
(2.2)PARACYCLOPHAN 97%
[2.2]Paracyclophane,98%
2.2ü-Paracyclophane, 99%
[2.2]-PARACYCLOPHANE 99+%
Cyclobis(benzene-1,4-dimethylene)
[2.2]-paracyclophane (Parylene N)
4,4'-DIMETHYLENE-1,2-DIPHENYLETHANE
4,4'-Ethylene(1,1'-ethylenebisbenzene)
Tricyclo[8,2,2,2]4,7 hexa-4,6,10,12,13,15-decane
TRICYCLO[8.2.2.2]HEXADECA-4,6,10,12,13,15-HEXAENE
Tricyclo[8,2,2,24,7]hexadeca-4,6,1,12,13,15-hexaene
TRICYCLO[8.2.2.24,7]HEXADECA-4,6,10,12,13,15-HEXAENE
Tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene
Tricyclo[8.2.2.24,7]hexadeca-4,6,10,12(1),13,15-hexaene
Di-p-xylylene
Tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaene | [EINECS(EC#)]
216-644-2 | [Molecular Formula]
C16H16 | [MDL Number]
MFCD00003707 | [MOL File]
1633-22-3.mol | [Molecular Weight]
208.3 |
| Chemical Properties | Back Directory | [Appearance]
WHITE TO LIGHT BEIGE CRYSTALS OR CRYSTAL. POWDER | [Melting point ]
285-288 °C(lit.)
| [Boiling point ]
282.51°C (rough estimate) | [density ]
1.0102 (estimate) | [vapor pressure ]
0.001Pa at 25℃ | [refractive index ]
1.5000 (estimate) | [storage temp. ]
Store below +30°C. | [form ]
powder to crystal | [color ]
White to Almost white | [Water Solubility ]
INSOLUBLE | [BRN ]
1910888 | [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 | [InChIKey]
OOLUVSIJOMLOCB-UHFFFAOYSA-N | [SMILES]
C12C=CC(=CC=1)CCC1C=CC(=CC=1)CC2 | [LogP]
5.14 at 20℃ | [NIST Chemistry Reference]
[2.2]Paracyclophane(1633-22-3) | [EPA Substance Registry System]
Tricyclo[8.2.2.24, 7]hexadeca-4,6,10,12,13,15- hexaene(1633-22-3) |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO LIGHT BEIGE CRYSTALS OR CRYSTAL. POWDER | [Description]
[2.2]Paracyclophane is used as an intermediate in organic synthesis or as a reagent in chemical reactions. It serves as the structural backbone of 4-toluenesulfinyl [2.2]p-dicyclohexane and can be used in the synthesis of various mono- and disubstituted [2.2]p-dicyclohexane derivatives. It can also be used for the preparation of metal complexes, and the interaction of the Ag+ cation with the cation -π of [2.2]paracyclophane can be used to synthesise Ag+ - [2.2]paracyclophane complexes using the Ag+ cation. The complex is formed by binding the cation Ag+ to three carbon atoms on a benzene ring of the [2.2]paracyclophane ligand using a cation-π interaction[1]. | [Characteristics]
Parylene N has excellent electronic properties, including low dissipation factor, high dielectric strength, and low dielectric constant. These properties are beneficial for applications involving printed circuit boards and signal transmission. The extra chlorine in Parylene D results in slightly higher operating temperature for Parylene D relative to Parylene C. | [Uses]
2,2]-Paracyclophane is the raw material for the synthesis of parylene which is widely used in microelectronic integrated circuit. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 46, p. 1043, 1981 DOI: 10.1021/jo00318a047 | [Flammability and Explosibility]
Notclassified | [Purification Methods]
Purify it by recrystallisation from AcOH. 1H-NMR : 1.62 (Ar-H) and -1.71 (CH2) [Waugh & Fessenden J Am Chem Soc 79 846 1957, IR and UV: Cram et al. J Am Chem Soc 76 6132 1954, Cram & Steinberg J Am Chem Soc 73 5691 1951. It complexes with unsaturated compounds: Cram & Bauer J Am Chem Soc 81 5971 1959, Syntheses: Brink Synthesis 807 1975, Givens et al. J Org Chem 44 16087 1979, Kaplan et al. Tetrahedron Lett 3665 1976]. [Beilstein 5 IV 2223.] | [References]
[1] DR. PETR VA?URA; Dr. T U; Prof David Sykora. Interaction of the Silver(I) Cation with [2.2]Paracyclophane: Experimental and Theoretical Study[J]. ChemistrySelect, 2022. DOI:10.1002/slct.202203008. |
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