Parylene N Chemical Properties

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. 

Sealed in dry,Room Temperature

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 Information

Hazard Codes 

Xi,C,F

Risk Statements 

11-34

Safety Statements 

24/25-45-36/37/39-26-16

WGK Germany 

3

RTECS 

YD2404000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29029080

MSDS

• Language:English Provider:Di-p-xylylene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Parylene N Usage And Synthesis

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].

Chemical Properties

WHITE TO LIGHT BEIGE CRYSTALS OR CRYSTAL. POWDER

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

Not classified

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.

Parylene N(1633-22-3)Related Product Information

• 1,2,5,6,9,10-Hexabromocyclododecane
• C36 Dimer acid
• CYCLODODECANE
• P-XYLENE
• P-MENTHANE
• Poly(dimethylsiloxane)
• POLY(ETHYLENE TEREPHTHALATE)
• Dichlorodi-p-xylylene
• (R)-(-)-4,12-BIS(DIPHENYLPHOSPHINO)-[2.2]-PARACYCLOPHANE
• racemic-4,12-Dihydroxy[2.2]paracyclophane,min.97%
• Racemic-4,12-dibromo[2.2]paracyclophane
• DICHLORO[(R)-(-)-4,12-BIS(DI(3,5-XYLYL)PHOSPHINO)-[2,2]-PARACYCLOPHANE][(1S,2S)-(-)-1,2-DIPHENYLETHYLENEDIAMINE]RUTHENIUM
• Dichloro[2,2]paracyclophane
• (S)-(+)-4,12-BIS(DI(3,5-XYLYL)PHOSPHINO)-[2.2]-PARACYCLOPHANE ,CTH-(S)-3,5-XYLYL-PHANEPHOS
• poly-p-xylene
• 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane
• (R)-(-)-4,12-BIS(DI(3,5-XYLYL)PHOSPHINO)-[2.2]-PARACYCLOPHANE, MIN. 95% CTH-(R)-3,5-XYLYL-PHANEPHOS
• 4,16-DIBROMO[2.2]PARACYCLOPHANE