13861-22-8

Basic information

• Product Name: PROPARGYL METHACRYLATE
• Synonyms: PROPARGYL METHACRYLATE;Methacrylic acid propargyl ester~2-Propyn-1-yl 2-methylpropenoate;prop-2-ynyl methacrylate;Methacrylicacidpropargylester;2-propyn-1-yl 2-methylpropenoate;Propargyl methacrylate, 98%, stab. with ca 50ppm BHT;2-Methylpropenoic acid 2-propynyl ester;Methacrylic acid 2-propynyl ester
• CAS NO: 13861-22-8
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• EINECS: 237-599-5
• Product Categories: monomer
• Mol File: 13861-22-8.mol

Chemical Properties

• Boiling Point: 149-151°C
• Flash Point: 48°C
• Appearance: /
• Density: 0,986 g/cm3
• Vapor Pressure: 4.23mmHg at 25°C
• Refractive Index: 1.4500
• Storage Temp.: -20°C
• Water Solubility: Immiscible with water.
• BRN: 906850
• CAS DataBase Reference: PROPARGYL METHACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPARGYL METHACRYLATE(13861-22-8)
• EPA Substance Registry System: PROPARGYL METHACRYLATE(13861-22-8)

Safety Data

• Statements: 10-36/37/38
• Safety Statements: 26-28
• RIDADR: 3272
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13861-22-8(Hazardous Substances Data)

Usage

Uses

Used in Polymer Synthesis:
Propargyl methacrylate is used as a monomer in polymerization reactions for the creation of alkyne-functionalized polymers and copolymers. The incorporation of alkynes allows for rapid post-polymerization modification, enhancing the versatility and functionality of the resulting polymers.
Used in Post-Polymerization Modification:
Propargyl methacrylate is used as a monomer to facilitate post-polymerization modification through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) or thiol-yne click reactions. These reactions are highly efficient and enable the easy installation of the desired functionality onto the biomolecule or small molecule of interest, making it a valuable component in the development of novel materials and applications.
Used in Polymerization Reactions through RAFT Process:
In the field of polymer chemistry, propargyl methacrylate is used as a monomer in reversible addition fragmentation chain transfer (RAFT) processes. This technique allows for better control over the polymerization process, resulting in polymers with more uniform molecular weights and structures. The RAFT process uses cyanoisopropyl dithiobenzoate as a reagent, further enhancing the versatility of propargyl methacrylate in polymer synthesis.

InChI:InChI=1/C7H8O2/c1-4-5-9-7(8)6(2)3/h1H,2,5H2,3H3

Upstream product

• 107-19-7 propargyl alcohol 
• 920-46-7 Methacryloyl chloride 
• 214268-06-1 2-methyl-acrylic acid 3-trimethylsilanyl-propyn-2-ynyl ester 
• 40630-86-2 2-bromo-2-methylpropionic acid-2-propynyl ester 

Downstream Products

• 19610-34-5 (1'-hydroxymethyl)-1,2-dicarba-closo-dodecaborane 
• 214268-06-1 2-methyl-acrylic acid 3-trimethylsilanyl-propyn-2-ynyl ester 

Relevant articles and documents

Controlling the lectin recognition of glycopolymers: Via distance arrangement of sugar blocks

The arrangement of sugars in glycopolymers contributes to their recognition. The molecular recognition of proteins was controlled by the living radical polymerization of glycopolymers. The glycopolymers were prepared by the copolymerization of propargyl methacrylate (Pr-MA) and triethyleneglycol methacrylate (TEG-MA) via living radical polymerization with a reversible addition-fragmentation glycopolymer chain transfer (RAFT) reagent and by subsequent sugar conjugation by click chemistry. The block copolymers were prepared by the polymerization of Pr-MA and TEG-MA. The molecular recognition of glycopolymers was analyzed using the fluorescence quenching of lectin and found to be dependent on the glycopolymer structures. Two-site binding of glycopolymers to concanavalin A (ConA) was attained by both the glycopolymer with a 105-mer and the tri-block glycopolymer with a 103-mer. Glycopolymers with either a 27- or 54-mer showed much weaker interaction because of one-site binding. The molecular recognition of the glycopolymer was controlled by the arrangement and size of the sugar cluster and not by the sugar density.

Multifunctional Giant Amphiphiles via simultaneous copper(i)-catalyzed azide-alkyne cycloaddition and living radical polymerization

A novel class of chemically addressable, multifunctional Giant Amphiphiles was synthesized in excellent yields and polydispersity following simultaneous or sequential living radical polymerization and the click, copper(i)-catalysed azide-alkyne cycloaddition (CuAAC). This new approach allows chemical tailoring of the biomacromolecules and in situ formation of nanocontainers.

Prop-2-yn-1-yl 2-Bromo-2-methylpropanoate: Identification and Suppression of Side Reactions of a Commonly Used Terminal Alkyne-Functional ATRP Initiator

The atom transfer radical polymerization (ATRP) of styrene was investigated using the popular alkyne-functional initiator prop-2-yn-1-yl 2-bromo-2-methylpropanoate (PBiB). The polymerization kinetics and evolution of molecular weight as a function of monomer conversion were systematically studied with PBiB and similar initiators with protecting groups at the reactive propargylic and terminal acetylenic sites. These studies were compared to control studies using the nonfunctional initiator ethyl 2-bromoisobutyrate. As confirmed by NMR analysis of a model reaction, the terminal alkynes undergo oxidative alkyne-alkyne coupling under ATRP conditions, resulting in polymers with bimodal molecular weight distributions. This side reaction is significant because it diminishes the orthogonality of ATRP/copper-catalyzed azide-alkyne cycloaddition procedures as well as the control of ATRP.

Optical switching, photophysical, and electrochemical behaviors of pendant triazole-linked indolylfulgimide polymer

Triazole-linked 2-indolylfulgimide polymer has been synthesized and its photochromic switching behavior has been characterized by NMR, IR, GPC, TGA, DSC, and UV-Vis spectroscopy. The synthesized photochromic polymer showed absorption peak maxima at 386 and 510 nm wherein the absorption at 510 nm was attributed to charge transfer from triazole ring nitrogen to carbonyl carbon of fulgimide unit. Fluorescence lifetime studies on exciting at 550 nm reveals triexponential behavior with fluorescence decay around 0.1, 1 and 4.2 ns, which correspond to open (E), closed (C) form of fulgimide and triazole ring, respectively. Whereas exciting at 470 nm evidences biexponential fit with fluorescence decay around 0.1 and 2.2 ns, which corresponds to the closed (C) form and triazole ring, respectively. Fluorescence decay of triazole ring was found to be influenced by the excitation wavelength. The cyclic voltammogram of open form of polymer depicts irreversible reductive wave at -1.4 V. On illumination with 360-nm light, the reduction wave of polymer was shifted toward less cathodic wave at -0.9 V; this leads to formation of the closed form of fulgimide unit.

Cyclodextrin-Based [3]Rotaxane-Crosslinked Fluorescent Polymer: Synthesis and De-Crosslinking Using Size Complementarity

Vinyl-group-substituted, α-cyclodextrin-based, size-complementary [3]rotaxanes were synthesized as crosslinkers for rotaxane-crosslinked poly(methyl methacrylate) (RCP) by radical polymerization. The size complementarity of the crosslinkers made it possible to de-crosslink the RCP by heating, and the degree of decoupling was monitored by fluorescence intensity, depending on the state of the axle component of the rotaxane crosslink moiety.

MRI-visible polymer based on poly(methyl methacrylate) for imaging applications

Macromolecular contrast agents are very attractive to afford efficient magnetic resonance imaging (MRI) visualization of implantable medical devices. In this work, we report on the grafting of a Gd-based DTPA contrast agent onto a poly(methyl methacrylate) derivative backbone by combining free radical polymerization and copper-catalyzed azide-alkyne cycloaddition (CuAAC). Using free radical polymerization, poly(methyl methacrylate-co-propargyl methacrylate) copolymers were prepared with a control of the ratio in propargyl methacrylate monomer units. The synthesis of a new azido mono-functionalized DTPA ligand was also reported and characterized by 1H NMR and mass spectroscopy. After complexation with gadolinium, this ligand has been grafted on the polymer backbone by click chemistry reaction. The obtained macromolecular contrast agent was then coated on a polypropylene mesh using the airbrushing technique and the mesh was assessed for MRI visualization at 7 teslas. The polymeric contrast agent was also tested for cytocompatibility and stability to assess its suitability for biomedical applications.

Site-directed conjugation of "clicked" glycopolymers to form glycoprotein mimics: Binding to mammalian lectin and induction of immunological function

Synthesis of well-defined neoglycopolymer-protein biohybrid materials and a preliminary study focused on their ability of binding mammalian lectins and inducing immunological function is reported. Crucial intermediates for their preparation are well-defined maleimide-terminated neoglycopolymers (M n = 8-30 kDa; Mw/Mn = 1.20-1.28) presenting multiple copies of mannose epitope units, obtained by combination of transition-metal-mediated living radical polymerization (TMM LRP) and Huisgen [2+3] cycloaddition. Bovine serum albumin (BSA) was employed as single thiol-containing model protein, and the resulting bioconjugates were purified following two independent protocols and characterized by circular dichroism (CD) spectroscopy, SDS PAGE, and SEC HPLC. The versatility of the synthetic strategy presented in this work was demonstrated by preparing a small library of conjugating glycopolymers that only differ from each other for their relative epitope density were prepared by coclicking of appropriate mixtures of mannopyranoside and galactopyranoside azides to the same polyalkyne scaffold intermediate. Surface plasmon resonance binding studies carried out using recombinant rat mannose-binding lectin (MBL) showed clear and dose-dependent MBL binding to glycopolymer-conjugated BSA. In addition, enzyme-linked immunosorbent assay (ELISA) revealed that the neoglycopolymer-protein materials described in this work possess significantly enhanced capacity to activate complement via the lectin pathway when compared with native unmodified BSA.