Bicyclohexyl

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Bicyclohexyl
Structural formula of bicyclohexyl
3D ball-and-stick structure of bicyclohexyl
Names
Preferred IUPAC name
1,1′-Bi(cyclohexane)
Other names
  • 1,1′-Bicyclohexyl
  • Bicyclohexane
  • Dicyclohexyl
  • Cyclohexylcyclohexane
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.001.966 Edit this at Wikidata
EC Number
  • 202-161-4
UNII
  • InChI=1S/C12H22/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11-12H,1-10H2
    Key: WVIIMZNLDWSIRH-UHFFFAOYSA-N
  • C1CCC(CC1)C2CCCCC2
Properties
C12H22
Molar mass 166.308 g·mol−1
Appearance Colorless liquid
Density 0.88273 g/cm3
Melting point 4 °C (39 °F; 277 K)
Insoluble
Solubility in other solvents Miscible with organic solvents
1.4796[1]
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H410
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501
Flash point 92 °C (198 °F; 365 K)
245 °C (473 °F; 518 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bicyclohexyl, also known as dicyclohexyl or bicyclohexane, is an organic chemical with the formula C12H22 and a molecular mass of 166.303 g mol−1. It is a nonvolatile liquid at room temperature, with a boiling point of 227 °C (441 °F). Its structure consists of two cyclohexane rings joined by a single carbon-carbon bond.

Production

Carbazole can be denitrogenated by hydrogen to yield bicyclohexyl as the main product.[2]

When cyclohexane is exposed to radiation, bicyclohexyl is produced among other hydrocarbons.[3]

Properties

The molecule is not completely flat, and the two rings are twisted compared to each other. Liquid bicyclohexyl contains a mixture of molecules with C2 and C2h symmetry termed ee anti, and ee gauche. The carbon-carbon bond (pivot) between the rings is 1.55 Å, and the carbon-carbon length in the rings is 1.535 Å and carbon-hydrogen bond length is 1.102 Å. The torsion angle between the rings is 74.9°. The C-C-C bond angle ∠ is about 111° and C-C-H angle is 109°.[4]

The

isothermal compressibility is 674 TPa−1 and isobaric expansivity is 819 K−1.[5]

When bicyclohexyl is heated to around 427 °C (801 °F) it slowly decomposes to cyclohexane and cyclohexene, as the pivot bond joining the two rings is the longest and weakest one.[6]

Heat of combustion is 1814.8 kcal/mol.[7]

Use

Bicyclohexyl has uses in organic synthesis as a building block and structural motif, in studying the chemistry of liquid interfaces,[8] and in surface modification of metal oxides as a solvent.[9]

See also

References

  1. ISBN 9781483272856
    .
  2. ISBN 9780824797560
    .
  3. doi:10.1063/1.1744261
    .
  4. doi:10.1016/0022-2860(91)80071-B
    .
  5. doi:10.1021/je00046a031
    .
  6. doi:10.1021/ef501077n
    .
  7. doi:10.1016/0021-9614(76)90015-X
    .
  8. doi:10.1021/la9508194
    .
  9. PMID 24849332
    .
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