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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:
906755
EC Number:
212-104-5
MDL number:
MFCD00008635
UNSPSC Code:
12352103
PubChem Substance ID:
24852502
NACRES:
NA.22

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

Signal Word

Danger

Hazard Statements

H225,H315

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Roman Schowner et al.
Angewandte Chemie (International ed. in English), 59(2), 951-958 (2019-11-28)
The origin of hydroxyl group tolerance in neutral and especially cationic molybdenum imido alkylidene N-heterocyclic carbene (NHC) complexes has been investigated. A wide range of catalysts was prepared and tested. Most cationic complexes can be handled in air without difficulty
Thierry Ollevier et al.
Organic & biomolecular chemistry, 4(24), 4440-4443 (2007-02-03)
We report the first catalytic Sakurai reaction of N-alkoxycarbonylamino sulfones with allylsilanes. The allylation reaction of N-alkoxycarbonylamino phenylsulfones with allyltrimethylsilane proceeded smoothly with low catalyst loading of bismuth triflate (2.0 mol%) to afford the corresponding protected homoallylic amines in moderate
Allyltrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)
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)
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