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.
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| Names | |
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| Preferred IUPAC name
Hexa-1,5-diene | |
| Other names
diallyl, biallyl, α,ω-Hexadiene
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.008.869 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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: | |
  
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| 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).
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Synthesis
edit1,5-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
edit- ^ Lionel Delaude; Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01. ISBN 9780471484943.
- ^ Amos Turk; Henry Chanan (1947). "Biallyl". Org. Synth. 27: 7. doi:10.15227/orgsyn.027.0007.