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Sigma-Aldrich

Allyltrimethoxysilane

95%

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Synonym(s):
Trimethoxy-2-propen-1-ylsilane, trimethoxy-2-propenylsilane
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

Quality Level

100

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

WGK

WGK 3

Flash Point(F)

114.8 °F

Flash Point(C)

46 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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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)
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

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