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681482

Sigma-Aldrich

2-(Allyldimethylsilyl)pyridine

90%

Synonym(s):

Allyldimethyl(2-pyridyl)silane

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About This Item

Linear Formula:
(CH2CHCH2)Si(CH3)2(C5H4N)
CAS Number:
118722-54-6
Molecular Weight:
177.32
MDL number:
MFCD09265157
UNSPSC Code:
12352103
PubChem Substance ID:
24885637
NACRES:
NA.22

Assay

90%

refractive index

n20/D 1.5046

density

0.913 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

C[Si](C)(CC=C)c1ccccn1

InChI

1S/C10H15NSi/c1-4-9-12(2,3)10-7-5-6-8-11-10/h4-8H,1,9H2,2-3H3

InChI key

WIRIPVDRZYVTCG-UHFFFAOYSA-N

Application

2-(Allyldimethylsilyl)pyridine can be used as a pyridyl transfer reagent to prepare substituted pyridine derivatives by reacting with various aryl iodides in the presence of a palladium catalyst and silver(I) oxide activator. It can also be utilized as a coupling reagent in the allylation of carbonyl compounds using a copper catalyst.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

160.0 °F - closed cup

Flash Point(C)

71.1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Toshiki Nokami et al.
Organic letters, 8(4), 729-731 (2006-02-14)
[reaction: see text] (2-Pyridyl)allyldimethylsilanes were found to be novel pyridyl transfer reagents in palladium-catalyzed cross-coupling reactions of various aryl iodides in the presence of silver(I) oxide as an activator.
Copper-catalyzed allylation of carbonyl derivatives using allyl (2-pyridyl) silanes
Kamei T, et al.
Organic Letters, 7(21), 4725-4728 (2005)
Palladium-catalyzed cross-coupling reactions of (2-pyridyl) allyldimethylsilanes with aryl iodides
Nokami T, et al.
Organic Letters, 8(4), 729-731 (2006)

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