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446955

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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

114.8 °F

flash_point_c

46 °C

ppe

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

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.

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