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Cyclohexa-1,4-diene

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Cyclohexa-1,4-diene
Skeletal formula with all implicit hydrogen shown, skeletal formula; stereo, skeletal formula with all explicit hydrogens added, all of 1,4-cyclohexadiene
Skeletal formula with all implicit hydrogen shown, skeletal formula; stereo, skeletal formula with all explicit hydrogens added, all of 1,4-cyclohexadiene
Names
Systematic IUPAC name Cyclohexa-1,4-diene
Other names 1,4-Cyclohexadiene
1,4-Dihydrobenzene
Identifiers
CAS Number
3D model (JSmol)
Abbreviations 1,4-CHDN
Beilstein Reference 1900733
ChEBI
ChemSpider
ECHA InfoCard 100.010.040 Edit this at Wikidata
EC Number
  • 211-043-1
Gmelin Reference 1656
MeSH 1,4-cyclohexadiene
PubChem CID
UN number 3295
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2Key: UVJHQYIOXKWHFD-UHFFFAOYSA-N
  • InChI=1/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2Key: UVJHQYIOXKWHFD-UHFFFAOYAM
SMILES
  • C1C=CCC=C1
Properties
Chemical formula C6H8
Molar mass 80.130 g·mol
Appearance Colorless liquid
Density 847 mg cm
Melting point −50 °C; −58 °F; 223 K
Boiling point 82 °C; 179 °F; 355 K
Refractive index (nD) 1.472
Thermochemistry
Heat capacity (C) 142.2 J K mol
Std molar
entropy (S298) 		189.37 J K mol
Std enthalpy of
formation (ΔfH298) 		63.0-69.2 kJ mol
Std enthalpy of
combustion (ΔcH298) 		-3573.5--3567.5 kJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS08: Health hazard
Signal word Danger
Hazard statements H225, H340, H350, H373
Precautionary statements P201, P210, P308+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 3 0
Flash point -7 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1,4-Cyclohexadiene is a highly flammable cycloalkene that occurs as a colorless clear liquid.

1,4-Cyclohexadiene and related compounds may be prepared from benzene using lithium or sodium in liquid ammonia, this process being known as a Birch reduction. However 1,4-cyclohexadiene is easily oxidised to benzene, the driving force being the formation of an aromatic ring. The conversion to an aromatic system may be performed in the laboratory using an alkene such as styrene, along with a hydrogen transfer agent such as palladium metal supported on charcoal.

γ-Terpinene is a naturally occurring derivative of 1,4-cyclohexadiene, found in the essential oils of coriander, lemon, and cumin.

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.

External links

Cycloalkenes
Alkenes
Dienes
Trienes
Tetraenes
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