901212
5-Methyl-5-propargyloxycarbonyl-1,3-dioxane-2-one
≥98.0%
Synonym(s):
Propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate
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About This Item
Empirical Formula (Hill Notation):
C9H10O5
CAS Number:
Molecular Weight:
198.17
UNSPSC Code:
12162002
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Assay
≥98.0%
form
powder or chunks
color
colorless to pale yellow
storage temp.
−20°C
General description
5-Methyl-5-propargyloxycarbonyl-1,3-dioxane-2-one is an alkyne-functionalized, cyclic carbonate monomer that can be polymerized or copolymerized to yield alkyne-functionalized polycarbonates. 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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Synthesis of ferrocene-functionalized monomers for biodegradable polymer formation.
Upton BM, et al.
Inorganic Chemistry, 1, 271-271 (2014)
Russell C Pratt et al.
Chemical communications (Cambridge, England), (1), 114-116 (2008-04-11)
Cyclic carbonate monomers based on a single biocompatible scaffold allow for incorporation of a wide range of functional groups into macromolecules via ring-opening polymerization.
Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s.
Tempelaar S, et al.
Polym. Chem., 4, 174-174 (2013)
Daniel P Sanders et al.
Journal of the American Chemical Society, 132(42), 14724-14726 (2010-10-05)
An improved two-step synthetic route to functionalized cyclic carbonate monomers that features a novel cyclic carbonate intermediate with an active pentafluorophenyl ester group (MTC-OPhF(5)) has been developed. The versatile pentafluorophenyl ester intermediate can be synthesized on the gram to kilogram
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