1,5-Hexadiene

1,5-Hexadiene is the organic compound with the formula (CH2)2(CH=CH2)2. It is a colorless, volatile liquid. It is used as a crosslinking agent and precursor to a variety of other compounds.

1,5-Hexadiene
Names
Preferred IUPAC name
Hexa-1,5-diene
Other names
diallyl, biallyl, α,ω-Hexadiene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.869
EC Number
  • 209-754-7
UNII
  • InChI=1S/C6H10/c1-3-5-6-4-2/h3-4H,1-2,5-6H2
    Key: PYGSKMBEVAICCR-UHFFFAOYSA-N
  • C=CCCC=C
Properties
C6H10
Molar mass 82.146 g·mol−1
Appearance colorless liquid
Boiling point 59–60 °C (138–140 °F; 332–333 K)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H225, H302, H305, H315, H319, H335, H336
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

1,5-Hexadiene is produced commercially by the ethenolysis of 1,5-cyclooctadiene:[1]

(CH2CH=CHCH2)2 + 2 CH2=CH2 → 2 (CH2)2CH=CH2

The catalyst is derived from Re2O7 on alumina.

A laboratory-scale preparation involves reductive coupling of allyl chloride using magnesium:[2]

2 ClCH2CH=CH2 + Mg → (CH2)2(CH=CH2)2 + MgCl2

References
  1. Lionel Delaude; Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01.
  2. Amos Turk; Henry Chanan (1947). "Biallyl". Org. Synth. 27: 7. doi:10.15227/orgsyn.027.0007.
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