208264
Allyltrimethylsilane
98%
Synonym(s):
3-(Trimethylsilyl)propene
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About This Item
Linear Formula:
H2C=CHCH2Si(CH3)3
CAS Number:
Molecular Weight:
114.26
Beilstein:
906755
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
form
liquid
refractive index
n20/D 1.407 (lit.)
bp
84-88 °C (lit.)
density
0.719 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
C[Si](C)(C)CC=C
InChI
1S/C6H14Si/c1-5-6-7(2,3)4/h5H,1,6H2,2-4H3
InChI key
HYWCXWRMUZYRPH-UHFFFAOYSA-N
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Application
Allyltrimethylsilane is a general reagent to introduce allyl groups across acid chlorides, aldehydes, ketones, iminium ions, enones, and for cross-coupling with other carbon electrophiles. It is used as a reagent in Hosomi−Sakurai reaction.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Flam. Liq. 2 - Skin Irrit. 2
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
60.8 °F - closed cup
Flash Point(C)
16 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Allyltrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Armando Ramirez et al.
Organic letters, 7(21), 4617-4620 (2005-10-08)
[reaction: see text] The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized
Allylation of Imines with Allyltrimethylsilane and Experimental Evidences for a Fluoride-Triggered Autocatalysis Mechanism of the Sakurai- Hosomi Reaction
Wang D, et al.
The Journal of Organic Chemistry, 64(12), 4233-4237 (1999)
Shoji Kobayashi et al.
Carbohydrate research, 343(3), 443-452 (2007-12-11)
An efficient route to the trans-fused tetrahydrooxepin corresponding to the E ring of ciguatoxin was developed. Wide screening of allylation reactions of sulfur or fluoro-substituted tetrahydrooxepin revealed that the optimum method for obtaining the beta-allylation product selectively was the use
Allyltrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)
Articles
Reagents for C–C Bond Formation
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