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208264

Sigma-Aldrich

Allyltrimethylsilane

98%

Synonym(s):

3-(Trimethylsilyl)propene

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About This Item

Linear Formula:
H2C=CHCH2Si(CH3)3
CAS Number:
762-72-1
Molecular Weight:
114.26
Beilstein/REAXYS Number:
906755
EC Number:
212-104-5
MDL number:
MFCD00008635
UNSPSC Code:
12352103
PubChem Substance ID:
24852502
NACRES:
NA.22

Quality Level

100

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H315

Hazard Classifications

Flam. Liq. 2 - Skin Irrit. 2

wgk_germany

WGK 3

flash_point_f

60.8 °F

flash_point_c

16 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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2-Bromoallyltrimethylsilane technical grade, 90%

Sigma-Aldrich

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Trimethylsilyl trifluoromethanesulfonate 99%

Sigma-Aldrich

225649

Trimethylsilyl trifluoromethanesulfonate

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)
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Reagents for C–C Bond Formation

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