1,4-Cyclohexadiene

Chembox new
ImageFile = 1-4-cyclohexadiene.png ImageSize = 240px
IUPACName = Cyclohexa-1,4-diene
OtherNames = 1,4-Cyclohexadiene, 1,4-Dihydrobenzene, 1,4-CHDN, CHDN
Section1 = Chembox Identifiers
CASNo = 628-41-1
EINECS = 211-043-1
PubChem = 12343
SMILES = C1C=CCC=C1
InChI = 1/C6H8/c1-2-4-6-5-3-1/h1-2,5-6H,3-4H2
ChEBI = 37611
Section2 = Chembox Properties
Formula = C₆H₈
MolarMass = 80.13 g/mol
Appearance = Colourless liquid
Density = 0.847 g/cm³
MeltingPt = -49.2 °C
BoilingPt = 88 °C
Solubility =
Section7 = Chembox Hazards
EUClass = Highly flammable (F+), Toxic (T)
MainHazards =
NFPA-H = 2
NFPA-F = 3
NFPA-R = 0
NFPA-O =
RPhrases = R11, R23/24/25, R36, R45, R48
SPhrases = S16, S27, S36/37/39, S45
FlashPt = -6 °C
Autoignition =

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

External links

* [http://physchem.ox.ac.uk/MSDS/CY/1,4-cyclohexadiene.html Safety MSDS data]
* [http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=b107991n&JournalCode=CP The photochemistry of 1,4-cyclohexadiene in solution and in the gas phase]