1,3-Cyclohexadiene

From Wikipedia, the free encyclopedia
Jump to: navigation, search
1,3-Cyclohexadiene
1-3-Cyclohexadiene.svg
1,3-cyclohexadiene-3D-balls.png 1,3-cyclohexadiene-3D-vdW.png
Identifiers
CAS number 592-57-4 YesY
PubChem 11605
ChemSpider 11117 YesY
ChEBI CHEBI:37610 YesY
RTECS number GU4702350
Jmol-3D images Image 1
Properties
Molecular formula C6H8
Molar mass 80.13 g/mol
Appearance Colourless liquid
Density 0.841 g/cm³
Melting point −98 °C (−144 °F; 175 K)
Boiling point 80 °C (176 °F; 353 K)
Hazards
EU classification Flammable (F)
R-phrases R11
S-phrases S9 S16 S29 S33
Flash point 26 °C (79 °F; 299 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

1,3-Cyclohexadiene is an organic compound with the formula (CH2)2(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). A naturally occurring derivative of 1,3-cyclohexadiene is terpinene, a component of pine oil.

Synthesis[edit]

Cyclohexadiene is prepared by the dehydrobromination of 1,2-dibromocyclohexane:[1]

(CH2)4(CHBr)2 + 2 NaH → (CH2)2(CH)4 + 2 NaBr + 2 H2

1,3-Cyclohexadiene can also be prepared by the electrocyclic reaction from 1,3,5-hexatriene either photochemically or at temperatures above 110 °C.[2]

Reactions[edit]

1,3-Cyclohexadiene can be used as a hydrogen donor in transfer hydrogenation, since its conversion to benzene + hydrogen is exothermic by about 20 kJ/mol (gas phase). [3][4]

cyclohexane → 1,3-cyclohexadiene + 2 H2 ΔH +224 kJ/mol (endothermic)
cyclohexane → benzene + + 3 H2 ΔH +205 kJ (endothermic)
1,3-cyclohexadiene → benzene + H2 ΔH -19 kJ (exothermic)

Compared with its isomer, 1,4-cyclohexadiene, 1,3-cyclohexadiene is about 1.6 kJ/mol less stable.[5]

See also[edit]

References[edit]

  1. ^ John P. Schaefer and Leland Endres (1967), 1,3-Cyclohexadiene, Org. Synth. 47: 31 ; Coll. Vol. 5: 285 
  2. ^ Roberts, Stanley (1995). Comprehensive Organic Functional Group Transformations: Synthesis: Carbon with No Attached Heteroatoms. Cambridge, UK: Elsevier Science Ltd. p. 419. ISBN 0080423221. 
  3. ^ US National Institute of Standards and Technology, NIST Chemistry WebBook 1,3-Cyclohexadiene Benzene
  4. ^ J. Sherman The heats of hydrogenation of unsaturated hydrocarbons Journal of the American Oil Chemists' Society; Volume 16, Number 2 / February, 1939
  5. ^ NIST Chemistry WebBook 1,4-Cyclohexadiene