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[2.2]Paracyclophane

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[2.2]Paracyclophane Basic information

Product Name:
[2.2]Paracyclophane
Synonyms:
  • TRICYCLO[8.2.2.24,7]HEXADECA-4,6,10,12,13,15-HEXAENE
  • TRICYCLO[8.2.2.2]HEXADECA-4,6,10,12,13,15-HEXAENE
  • [2.2]paracylophan
  • Cyclobis(benzene-1,4-dimethylene)
  • Di-1,4-xylylene
  • Tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene
  • 4,4'-DIMETHYLENE-1,2-DIPHENYLETHANE
  • [2.2]PARACYCLOPHAN
CAS:
1633-22-3
MF:
C16H16
MW:
208.3
EINECS:
216-644-2
Product Categories:
  • coating
  • Arenes
  • fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials
  • Building Blocks
  • Chemical Synthesis
  • Organic Building Blocks
  • Cyclophanes
  • Functional Materials
  • Macrocycles for Host-Guest Chemistry
  • 1
Mol File:
1633-22-3.mol
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[2.2]Paracyclophane 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
InChIKey
OOLUVSIJOMLOCB-UHFFFAOYSA-N
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)
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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

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[2.2]Paracyclophane Usage And Synthesis

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.]

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