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Sigma-Aldrich

Allyltrimethoxysilane

95%

Synonym(s):

Trimethoxy-2-propen-1-ylsilane, trimethoxy-2-propenylsilane

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About This Item

Linear Formula:
H2C=CHCH2Si(OCH3)3
CAS Number:
2551-83-9
Molecular Weight:
162.26
Beilstein:
2350745
EC Number:
219-855-8
MDL number:
MFCD00053865
UNSPSC Code:
12352103
PubChem Substance ID:
24868309
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.405 (lit.)

bp

146-148 °C (lit.)

density

0.963 g/mL at 25 °C (lit.)

SMILES string

CO[Si](CC=C)(OC)OC

InChI

1S/C6H14O3Si/c1-5-6-10(7-2,8-3)9-4/h5H,1,6H2,2-4H3

InChI key

LFRDHGNFBLIJIY-UHFFFAOYSA-N

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Application

Allyltrimethoxysilane is an allylating reagent that can be used for the allylation of carbonyl compounds such as aldehydes, ketones, and imines. Homoallylic alcohols and amines are obtained via the C-C bond forming reaction. It can also be used to synthesize homoallylic α-branched amines from aromatic and aliphatic aldehyde hydrazones, and ketone hydrazones.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

114.8 °F - closed cup

Flash Point(C)

46 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Hisashi Yamamoto et al.
Chemistry, an Asian journal, 2(6), 692-698 (2007-05-25)
Recently, there have been some reports on the use of allyltrimethoxysilane for enantioselective allylation with various metal fluorides or a combination of chiral complex and fluoride anion. These reactions can be applied not only to aldehydes but also to ketones
Shingo Yamasaki et al.
Journal of the American Chemical Society, 124(23), 6536-6537 (2002-06-06)
A general and mild catalytic allylation of carbonyl compounds, applicable to aldehydes, ketones, and imines is developed using allyltrimethoxysilane as the allylating reagent. The reaction proceeds smoothly with 1-10 mol % of CuCl and TBAT in THF at ambient temperature.
Allyltrimethoxysilane addition to N-acylhydrazones: Two catalytic methods employing CuCl and fluoride
Ding H and Friestad GK
Synthesis, 2004(13), 2216-2221 (2004)

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