Allyltrimethoxysilane

Name: Allyltrimethoxysilane
Brand: ALDRICH

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

UNSPSC Code:

12352103

NACRES:

NA.22

PubChem Substance ID:

24868309

EC Number:

219-855-8

Beilstein/REAXYS Number:

2350745

MDL number:

MFCD00053865

Key Documents

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InChI key

LFRDHGNFBLIJIY-UHFFFAOYSA-N

InChI

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

SMILES string

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

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.)

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Chemical Synthesis

Organosilicon Reagents

Silanes

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Show Differences

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This Item	58035	413364	107778
Sigma-Aldrich 446955 Allyltrimethoxysilane	Sigma-Aldrich 58035 (3-Iodopropyl)trimethoxysilane	Sigma-Aldrich 413364 3-(Triethoxysilyl)propyl isocyanate	Sigma-Aldrich 107778 Allyltrichlorosilane
assay 95%	assay ≥95.0% (GC)	assay 95%	assay 95%
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 100
density 0.963 g/mL at 25 °C (lit.)	density 1.482 g/mL at 20 °C (lit.)	density 0.999 g/mL at 25 °C (lit.)	density 1.211 g/mL at 25 °C (lit.)
refractive index n20/D 1.405 (lit.)	refractive index n20/D 1.473 (lit.)	refractive index n20/D 1.42 (lit.)	refractive index n20/D 1.443 (lit.)
bp 146-148 °C (lit.)	bp -	bp 283 °C (lit.)	bp 116 °C/750 mmHg (lit.)
form liquid	form -	form liquid	form -

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.[1][2] It can also be used to synthesize homoallylic α-branched amines from aromatic and aliphatic aldehyde hydrazones, and ketone hydrazones.

pictograms

GHS02,GHS07

signalword

Warning

hcodes

H226,H315,H319,H335

pcodes

P210 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

114.8 °F - closed cup

flash_point_c

46 °C - closed cup

ppe

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

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A general catalytic allylation using allyltrimethoxysilane.

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)

Silver-catalyzed asymmetric allylation: allyltrimethoxysilane as a remarkable reagent.

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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