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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

208264-BULK:
208264-10G:
208264-50G:
208264-VAR:
208264-10ML:
208264-50ML:

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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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
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)
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
Ming Yu et al.
Organic letters, 5(24), 4639-4640 (2003-11-25)
[reaction: see text] Direct allylation of glycal-derived donor-acceptor cyclopropanes has been achieved with TiCl(4) activation followed by addition of allyltrimethylsilane. The alpha diastereomer is the major product, with selectivities ranging from 3:1 to 10:1 and yields around 80%.
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