22235-02-5

Basic information

• Product Name: Dipropargyl ether
• Synonyms: Benzene,1,1'-(1-methylethylidene)bis[4-(2-propynyloxy)- (9CI); Propane,2,2-bis[p-(2-propynyloxy)phenyl]- (7CI,8CI);2,2-Bis[(4-propargyloxy)phenyl]propane; Bisphenol A bis(propargyl ether);Bisphenol A dipropargyl ether
• CAS NO: 22235-02-5
• Molecular Formula: C₂₁H₂₀O₂
• Molecular Weight: 0
• Mol File: 22235-02-5.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Dipropargyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Dipropargyl ether(22235-02-5)
• EPA Substance Registry System: Dipropargyl ether(22235-02-5)

Safety Data

• Hazardous Substances Data: 22235-02-5(Hazardous Substances Data)

Upstream product

• 80-05-7 BPA 
• 7705-08-0 iron(III) chloride 
• 624-65-7 2-propynyl chloride 
• 106-96-7 propargyl bromide 

Relevant articles and documents

Exploring thiol-yne based monomers as low cytotoxic building blocks for radical photopolymerization

The last decade has seen a remarkable interest in the development of biocompatible monomers for the realization of patient specific medical devices by means of UV-based additive manufacturing technologies. This contribution deals with the synthesis and investigation of novel thiol-yne based monomers with a focus on their biocompatibility and also the mechanical properties in their cured state. It could be successfully shown that propargyl and but-1-yne-4-yl ether derivatives have a significant lower cytotoxicity than the corresponding (meth)acrylates with similar backbones. Together with appropriate thiol monomers, these compounds show reactivities in the range of (meth)acrylates and almost quantitative triple bond conversions. A particular highlight is the investigation of the network properties of photo cured alkynyl ether/thiol resins by means of low field solid state nuclear magnetic resonance spectroscopy. Additionally, dynamic mechanical analysis of those polymers revealed that monomers containing rigid backbones lead to moduli and glass transition temperatures (Tg's), sufficiently high for the fabrication of medical devices by UV based additive manufacturing methods.

Thermally curable acetylene-containing main-chain benzoxazine polymers via sonogashira coupling reaction

Propargyl containing thermally curable benzoxazine precursors in the main chain have been synthesized from iodo functional bisbenzoxazine and diacetylenes by Sonogashira coupling reaction. For this purpose, 4,4′- isopropylidenediphenol (Bisphenol A) was reacted with formaldehyde and iodoaniline to form diiodobisbenzoxazine (DIBB). Sonogashira coupling reaction between DIBB and diacetylene bisether (DABE) or diacetylene bisbenzoxazine (DABB) catalyzed by palladium tetrakistriphenylphosphine yields the corresponding main-chain polybenzoxazine precursors with the molecular weights around 2300-3500 Da. The structures of the monomers and the resulting polymers are confirmed by FT-IR and 1H NMR spectral analysis. Curing behaviors of both the monomer and polymers were studied by differential scanning calorimetry (DSC). Thermal properties of the cured polymers were also investigated by thermogravimetric analysis (TGA).

Dipropargyl ether bisphenol A based boron-containing polymer: Synthesis, characterization and molecular dynamics simulations of the resulting pyrolysis and carbonization

Boron-containing polymers have recently attracted worldwide attention due to their ability to affect the thermal and oxidation resistance of an in situ formed material during pyrolytic carbonization. In this work, a novel dipropargyl ether bisphenol A based boron-containing (PB) precursor polymer, which can thermally cure via propargyl groups, was synthesized. PB was characterized with Fourier transform infrared spectroscopy and nuclear magnetic resonance (1H, 11B and 13C). Thermogravimetric analysis indicated the outstanding thermo-oxidative stability of PB thermosets with the temperature of 5% weight loss of 362 °C and char yield of 56.7% at 800 °C in air, while those are 416 °C and 74.0%, respectively, in nitrogen. The time evolution of major pyrolysis products including pyrolysis mechanism of PB thermosets were examined via thermogravimetry-Fourier transform infrared spectra as well as reactive molecular dynamics (ReaxFF-MD) simulations. In addition, the carbonized structure of PB thermosets was analyzed using X-ray photoelectron spectroscopy and X-ray powder diffraction. Formation of the graphitic fragment was simulated with ReaxFF-MD. Combining the ReaxFF-MD simulation with the experimental analysis, the way that boron atoms insert into the graphitic structure was illustrated.

Ultrasound Promoted Step-Growth Polymerization and Polymer Crosslinking Via Copper Catalyzed Azide–Alkyne “Click” Reaction

Mechano-activated chemistry is a powerful tool for remodeling of synthetic polymeric materials, however, few reactions are currently available. Here we show that using piezochemical reduction of a CuII-based pre-catalyst, a step-growth polymerization occurs via the copper catalyzed azide–alkyne cycloaddition (CuAAC) reaction to form a linear polytriazole. Furthermore, we show that a linear polymer can be crosslinked mechanochemically using the same chemistry to form a solid organogel. We envision that this chemistry can be used to harness mechanical energy for constructive purposes in polymeric materials.