1,5-Hexadiene

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1,5-Hexadiene
1,5-hexadienestick.png
Names
Other names
diallyl, biallyl, α,ω-Hexadiene
Identifiers
  • 592-42-7
3D model (JSmol)
  • Interactive image
ChemSpider
  • 11110
ECHA InfoCard 100.008.869
EC Number 209-754-7
PubChem CID
  • 11598
UNII
  • 4MTZ4764FI
Properties
C6H10
Molar mass 82.15 g·mol−1
Appearance colorless liquid
Boiling point 59–60 °C (138–140 °F; 332–333 K)
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H225, H304, H315, H319, H335, H336
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+310, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P331, P332+313, P337+313, P362, P370+378, P403+233, P403+235, P405
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

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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