| Identification | Back Directory | [Name]
Silane, trimethyl(2-methylene-3-buten-1-yl)- | [CAS]
70901-64-3 | [Synonyms]
Silane, trimethyl(2-methylene-3-buten-1-yl)- | [Molecular Formula]
C8H16Si | [MOL File]
70901-64-3.mol | [Molecular Weight]
140.3 |
| Hazard Information | Back Directory | [Physical properties]
bp 69–70 °C/80 mmHg. | [Uses]
2-Trimethylsilylmethyl-1,3-butadiene is an isoprenylation reagent; Diels–Alder diene; reactant in Formation of π-Allylic Complex Followed by Acyldemetalation. | [Preparation]
2-Trimethylsilylmethyl-1,3-butadiene is prepared most conveniently by the
coupling reaction of the Grignard reagent prepared from
(chloromethyl)trimethylsilane with 2-chloro-1,3-butadiene
(chloroprene) in the presence of a catalytic amount of Ni[Ph2P-
(CH2)3PPh2]Cl2 (91% yield) (eq 1). Alternatively, it can be
prepared by the reaction of the same Grignard reagent with allenylmethyl
phosphate in 57¨C73% yield (eq 2). Direct metalation
of isoprene followed by the reaction with chlorotrimethylsilane
gives 2-trimethylsilylmethyl-1,3-butadiene in low
yield. Thermal isomerization of 1-trimethylsilylmethylcyclobutene
to 2-trimethylsilylmethyl-1,3-butadiene has also
been reported.
| [storage]
Silane, trimethyl(2-methylene-3-buten-1-yl)- can be stored in a glass bottle under nitrogen.
| [Purification Methods]
Silane, trimethyl(2-methylene-3-buten-1-yl)- is purified by distillation.
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