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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-104-5
Beilstein/REAXYS Number:
906755
MDL number:
InChI key
HYWCXWRMUZYRPH-UHFFFAOYSA-N
InChI
1S/C6H14Si/c1-5-6-7(2,3)4/h5H,1,6H2,2-4H3
SMILES string
C[Si](C)(C)CC=C
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
Quality Level
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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.
signalword
Danger
hcodes
Hazard Classifications
Flam. Liq. 2 - Skin Irrit. 2
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
60.8 °F - closed cup
flash_point_c
16 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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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
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
Allyltrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Ionic liquid-promoted, highly regioselective heck arylation of electron-rich olefins by aryl halides
Mo J, et al.
Journal of the American Chemical Society, 127(2), 751-760 (2005)
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