ChemicalBook CAS DataBase List 1633-22-3

1633-22-3

Name	[2.2]Paracyclophane
CAS	1633-22-3
EINECS(EC#)	216-644-2
Molecular Formula	C16H16
MDL Number	MFCD00003707
Molecular Weight	208.3
MOL File	1633-22-3.mol

Chemical Properties

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)

Safety Data

Hazard Codes	Xi,C,F
Risk Statements	11-34 less more
Safety Statements	24/25-45-36/37/39-26-16 less more
WGK Germany	3
RTECS	YD2404000
Hazard Note	Irritant
TSCA	Yes
HS Code	29029080

Hazard Information

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].

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.

Material Safety Data Sheet(MSDS)

Spectrum Detail

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