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

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]

${\displaystyle {\ce {(CH3)3C-CH=C(CH3)2}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\ce {(CH3)3C-CH=}}{\color {red}{\ce {CH2}}}+{\ce {(CH3)2C=}}{\color {red}{\ce {CH2}}}}$

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