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901223

Sigma-Aldrich

3-(Trimethylsilyl)propargyl methacrylate

≥98.0%, contains 200 ppm MEHQ as inhibitor

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About This Item

Empirical Formula (Hill Notation):
C10H16O2Si
CAS Number:
214268-06-1
Molecular Weight:
196.32
MDL number:
MFCD29067305
UNSPSC Code:
12162002

Assay

≥98.0%

form

liquid

contains

200 ppm MEHQ as inhibitor

color

colorless to pale yellow

shipped in

wet ice

storage temp.

−20°C

General description

3-(Trimethylsilyl)propargyl methacrylate is a methacrylate-based monomer for use in the synthesis of alkyne-functionalized polymers and copolymers. The incorporation of alkynes allows for rapid post-polymerization modification through reactions, such as copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) or thiol-yne click reactions. These reactions are highly preferable for functionalization due their high efficiency and the ability to easily install the corresponding functionality (e.g., azides or thiols) onto the biomolecule or small molecule of interest. While alkynes offer great promise for post-polymerization functionalization, it is difficult to polymerize bifunctional, alkyne-containing monomers without the synthesis of branched or highly gelled products. 3-(Trimethylsilyl)propargyl methacrylate features a silyl-protected alkyne that can be easily deprotected post-polymerization to yield alkyne-functionalized polymers and copolymers.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

193.1 °F

Flash Point(C)

89.5 °C

Certificates of Analysis (COA)

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Graft block copolymers of propargyl methacrylate and vinyl acetate via a combination of RAFT/MADIX and click chemistry: Reaction analysis.
Quemener, D. et al
Journal of Polymer Science Part A: Polymer Chemistry, 46, 155-173 (2008)
Vincent Ladmiral et al.
Journal of the American Chemical Society, 128(14), 4823-4830 (2006-04-06)
The synthesis of novel well-defined alkyne side chain functional polymers featuring narrow molecular weight distributions (PDI = 1.09-1.17) by living radical polymerization is described. Grafting of protected and unprotected carbohydrates is achieved via either a C-6 or an anomeric azide
Clickable initiators, monomers and polymers in controlled radical polymerizations?a prospective combination in polymer science.
Mansfeld, U. et al
Polym. Chem., 1, 1560-1598 (2010)

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