Cyclohexa-1,4-diene

1,4-Cyclohexadiene is an organic compound with the formula C6H8. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an examples being γ-terpinene. An isomer exists of this compound, 1,3-cyclohexadiene.

Cyclohexa-1,4-diene
1,4-Cyclohexadiene molecule
1,4-Cyclohexadiene molecule
Names
Systematic IUPAC name
Cyclohexa-1,4-diene[1]
Other names
1,4-Cyclohexadiene
1,4-Dihydrobenzene
Identifiers
3D model (JSmol)
Abbreviations 1,4-CHDN
1900733
ChEBI
ChemSpider
ECHA InfoCard 100.010.040
EC Number
  • 211-043-1
1656
MeSH 1,4-cyclohexadiene
UNII
UN number 3295
Properties
C6H8
Molar mass 80.130 g·mol−1
Appearance Colorless liquid
Density 0.847 g cm−3
Melting point −50 °C; −58 °F; 223 K
Boiling point 82 °C; 179 °F; 355 K
-48.7·10−6 cm3/mol
1.472
Thermochemistry
142.2 J K−1 mol−1
189.37 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 63.0-69.2 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 -3573.5--3567.5 kJ mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H340, H350, H373
P201, P210, P308+313
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point −7 °C (19 °F; 266 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis and reactions

In the laboratory, substituted 1,4-cyclohexadienes are synthesized by Birch reduction of related aromatic compounds using an alkali metal and a proton donor such as ammonia. In this way, over reduction to the fully saturated ring is avoided.

1,4-Cyclohexadiene and its derivatives are easily aromatized, the driving force being the formation of an aromatic ring. The conversion to an aromatic system may be used to trigger other reactions, such as the Bergman cyclization.[2]

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References
  1. "1,4-cyclohexadiene - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 12 October 2011.
  2. John C. Walton, Fernando Portela-Cubillo "1,4-Cyclohexadiene" Encyclopedia of Reagents for Organic Synthesis 2007 John Wiley & Sons. doi:10.1002/047084289X.rn00806
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