Neohexene

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.

Neohexene

Names
Preferred IUPAC name 3,3-Dimethylbut-1-ene
Other names 3,3-Dimethyl-1-butene
Identifiers
CAS Number	558-37-2
3D model (JSmol)	Interactive image
ChemSpider	10737
ECHA InfoCard	100.008.361
EC Number	209-195-9
PubChem CID	11210
UNII	01ZB73D2KK
CompTox Dashboard (EPA)	DTXSID1027211
InChI InChI=1/C6H12/c1-5-6(2,3)4/h5H,1H2,2-4H Key: PKXHXOTZMFCXSH-UHFFFAOYSA-N
SMILES CC(C)(C)C=C
Properties
Chemical formula	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). Infobox references

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. 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.