Neohexene

Neohexene
Names
Preferred IUPAC name
3,3-Dimethylbut-1-ene
Other names
3,3-Dimethyl-1-butene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.361 Edit this at Wikidata
EC Number
  • 209-195-9
UNII
  • InChI=1/C6H12/c1-5-6(2,3)4/h5H,1H2,2-4H
    Key: PKXHXOTZMFCXSH-UHFFFAOYSA-N
  • CC(C)(C)C=C
Properties
C6H12
Molar mass 84.162 g·mol−1
Appearance colorless liquid
Density 0.685 g mL−1
Boiling point 41 °C (106 °F; 314 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Neohexene is the hydrocarbon compound with the chemical formula (CH3)3CCH=CH2. It is a colorless liquid, with properties similar to other hexenes. It is a precursor to commercial synthetic musk perfumes.

Preparation and reactions

Neohexene is prepared by ethenolysis of diisobutene, an example of a metathesis reaction:[1]

(CH3)3C-CH=C(CH3)2 + CH2=CH2 → (CH3)3C-CH=CH2 + (CH3)2C=CH2

It is a building block to synthetic musks by its reaction with p-cymene. It is also used in the industrial preparation of terbinafine.[1]

In the study of C-H activation, neohexene is often used as a hydrogen acceptor.[2]

References

  1. ^ a b Delaude, Lionel; Noels, Alfred F. (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01.
  2. ^ Liu, Fuchen; Pak, Esther B.; Singh, Bharat; Jensen, Craig M.; Goldman, Alan S. (1999). "Dehydrogenation of n-Alkanes Catalyzed by Iridium "Pincer" Complexes: Regioselective Formation of α-Olefins". J. Am. Chem. Soc. 121 (16): 4086–4087. doi:10.1021/JA983460P.

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