1,5-Hexadiene

1,5-Hexadiene

Names
Preferred IUPAC name Hexa-1,5-diene
Other names diallyl, biallyl, α,ω-Hexadiene
Identifiers
CAS Number	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
CompTox Dashboard (EPA)	DTXSID4049323
InChI InChI=1S/C6H10/c1-3-5-6-4-2/h3-4H,1-2,5-6H2 Key: PYGSKMBEVAICCR-UHFFFAOYSA-N
SMILES C=CCCC=C
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H305, H315, H319, H335, H336
Precautionary statements	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

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:

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