10477-47-1

Basic information

• Product Name: PROPARGYL ACRYLATE
• Synonyms: 2-propenoicacid,2-propynylester;PROPARGYL ACRYLATE;TIMTEC-BB SBB008981;ACRYLIC ACID PROPARGYL ESTER;Acrylic acid propargyl ester~2-Propyn-1-yl propenoate;2-propynyl acrylate;2-propyn-1-yl propenoate;Propargyl acrylate, 95%, stab. with ca 200ppm BHT
• CAS NO: 10477-47-1
• Molecular Formula: C₆H₆O₂
• Molecular Weight: 110.11
• EINECS: 233-975-8
• Product Categories: monomer
• Mol File: 10477-47-1.mol

Chemical Properties

• Boiling Point: 142-143 °C(lit.)
• Flash Point: 110 °F
• Appearance: /
• Density: 0.997 g/mL at 25 °C(lit.)
• Vapor Pressure: 10.3mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Water Solubility: Not miscible or difficult to mix with water.
• BRN: 1902961
• CAS DataBase Reference: PROPARGYL ACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPARGYL ACRYLATE(10477-47-1)
• EPA Substance Registry System: PROPARGYL ACRYLATE(10477-47-1)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 10477-47-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Propargyl acrylate is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs and therapeutic agents.
Used in Polymer Synthesis:
Propargyl acrylate is used as a monomer in the synthesis of linear poly(N-isopropylacrylamide) (PNIPAM), a temperature-responsive polymer with potential applications in drug delivery and other biomedical fields.
Used in Chain Transfer Agent Production:
It is also utilized in the synthesis of 1-[3-(2-methyl-2-dodecylsulfanylthiocarbonylsulfanylpropionyloxy)propyl]-1H-[1,2,3]triazol-4-ylmethyl acrylate, an acryloyl trithiocarbonate chain transfer agent. This agent is essential in controlling the molecular weight and architecture of polymers, which is crucial for their performance in various applications.
Used in Nanoparticle Synthesis:
Propargyl acrylate is employed in the development of propranolol-imprinted core-shell nanoparticles (mipCS). These nanoparticles have the ability to selectively recognize and bind to specific target molecules, making them valuable in drug delivery and sensing applications.

InChI:InChI=1/C6H6O2/c1-3-5-8-6(7)4-2/h1,4H,2,5H2

Upstream product

• 107-19-7 propargyl alcohol 
• 814-68-6 acryloyl chloride 
• 4383-39-5 Propiolsaeure-(2-propinyl)ester 

Downstream Products

• 1166168-40-6 1-Phenyl-4-acryloyloxymethyl-triazole 
• 1588498-21-8 N-(tert-butoxycarbonyl)-L-isoleucyl-N²-(2,4-dimethoxybenzyl)-N₁-{(1S)-2-[4-({[3-(2-ethyl-8-methyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propanoyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]-1-methylethyl}-2-methylalaninamide 
• 1588498-22-9 N-(tert-butoxycarbonyl)-L-isoleucyl-N²-(2,4-dimethoxybenzyl)-N₁-{(1S)-2-[4-({[3-(8-fluoro-2-methyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propanoyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]-1-methylethyl}-2-methylalaninamide 
• 1588498-23-0 N-(tert-butoxycarbonyl)-L-isoleucyl-N²-(2,4-dimethoxybenzyl)-N₁-{(1S)-2-[4-({[3-(2,8-dimethyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propanoyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]-1-methylethyl}-2-methylalaninamide 
• 1588498-24-1 N-(tert-Butoxycarbonyl)-L-isoleucyl-N²-(2,4-dimethoxybenzyl)-N₁-{(1S)-2-[4-({[3-(8-methoxy-2-methyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propanoyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]-1-methylethyl}-2-methylalaninamide 
• 1588498-25-2 N-(tert-butoxycarbonyl)-L-seryl-N²-(2,4-dimethoxybenzyl)-N₁-((1S)-1-{[4-({[3-(2,8-dimethyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propanoyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]methyl}-2-methylpropyl)glycinamide 
• 1588498-26-3 N-(tert-butoxycarbonyl)-L-phenylalanyl-N²-(2,4-dimethoxybenzyl)-N₁-{(1S)-2-[4-({[3-(2,8-dimethyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propanoyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]-1-methylethyl}-2-methylalaninamide 
• 1588498-27-4 N-(tert-butoxycarbonyl)-L-alanyl-N¹-{2-[4-({[3-(2,8-dimethyl-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)propanoyl]oxy}methyl)-1H-1,2,3-triazol-1-yl]ethyl}-N₂-(4-methoxybenzyl)-2-methylalaninamide 

Related news

Bubble-point measurement for the binary mixture of PROPARGYL ACRYLATE (cas 10477-47-1) and propargyl methacrylate in supercritical carbon dioxide07/31/2019

Acrylate and methacrylate (acrylic acid type) are compounds with weak polarity which show a non-ideal behaviour. Phase behaviour of these systems play a significant role as organic solvents in industrial processes. High pressure phase behaviour data were reported for binary mixture of propargyl ...detailed

Relevant articles and documents

NMRP versus "click" chemistry for the synthesis of semiconductor polymers carrying pendant perylene bisimides

The synthesis of well-defined polymers with pendant perylene bisimide (PBI) groups by a combination of nitroxide-mediated radical polymerization (NMRP) of trimethylsilyl propargyl acrylate followed by copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click" chemistry) is described. The kinetics of NMRP of trimethylsilyl propargyl acrylate polymerization was monitored by 1H NMR and size exclusion chromatography (SEC). Almost quantitative conversion in the "click" reaction with an azide functionalized PBI derivative was proven by FTIR and 1H NMR analysis. Thus, semiconductor polymers carrying PBI pendant groups with Mn up to 15800 g·mol-1 and polydispersity indices as good as 1.16 were obtained by this route. These polymers were compared with poly(perylene bisimide acrylate)s, PPerAcr(CH2)11, and PPerAcr(CH 2)6, which were synthesized by direct NMRP of PBI acrylates. These samples do not carry any triazol unit and they differ in their spacer length connecting the PBI unit to the main chain. All polymers were comparatively studied by SEC, thermogravimetry, differential scanning calorimetry, polarization microscopy, UV/vis spectroscopy, and photoluminescence measurements. The crystalline structure of the polymers was analyzed by X-ray diffraction. Inductively coupled plasma mass spectrometry analysis confirmed that copper content in the "click" polymer could be reduced down to 126 ppm (w/w).

Development of micellar novel drug carrier utilizing temperature-sensitive block copolymers containing cyclodextrin moieties

A drug-delivery system for albendazole (ABZ) based on β-cyclodextrin has been synthesized. Well-defined statistical copolymers, composed of N-isopropylacrylamide (NIPAAM) and trimethylsilylpropargyl acrylate (TMSPA), have been prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. The reactivity ratios were determined to be rTMSPA = 1.12 and rNIPAAm = 0.49, in the absence of RAFT agent, and r TMSPA = 1.35 and rNIPAAm = 0.35, in the presence of RAFT agent using the average of different techniques. Block copolymers were prepared using a POEGMEA40 macro-RAFT agent chain extended with NIPAAm and TMSPA in various feed ratios. After deprotection, the polymers were reacted with 6I-azido-6I-deoxy-β-cyclodextrin via Huisgen azide-alkyne 1,3-dipolar cycloaddition, resulting in thermo-responsive block copolymers with pendant β-cyclodextrin groups, which were then acetylated to modify the polarity and inclusion-complex formation of β-cyclodextrin with the drug albendazole (ABZ). Only block copolymers with small amounts of cyclodextrin were observed to have an LCST while the copolymers containing higher β-cyclodextrin fractions increased the LCST of PNIPAAm beyond measurable temperature ranges. Encapsulation of ABZ increased the LCST. The loading efficiency increased in the polymer β-cyclodextrin conjugate compared to native β-cyclodextrin with the highest loading observed in the block copolymer after all remaining cyclodextrin hydroxyl groups had been acetylated. While β-cyclodextrin is toxic, attachment of a polymer lowered the toxicity to nontoxic levels. The ABZ-loaded polymers were all observed to be highly toxic to OVCAR-3 ovarian cancer cell lines with the acetylated polymer showing the highest toxicity.

Construction of an Artificial Glutathione Peroxidase Active Site on Copolymer Vesicles

To construct an efficient GPx mimic, a novel method for preparing polymer-based vesicles carrying GPx-active sites was developed. A series of block copolymers loaded with recognition and catalytic sites were synthesized based on polystyrene-block-poly[tri(ethylene glycol) methyl ether acrylate]s (PS-PMEO3MAs). By altering the molar ratio of the functional copolymers, vesicles with GPx activity were obtained by self-assembly of these functional copolymers through blending. The optimum GPx mimic constructed by the blending process exhibited high catalytic activity and acted as a real catalyst with typical saturation kinetics behavior. The method may be of benefit for designing other enzyme mimics and may cast a light on constructing other biologically related functional nanoparticles.Self-assembly of functional copolymers through blending is a novel and simple method to construct efficient glutathione peroxidase(GPx) mimics. The optimum blended GPx mimic is obtained by optimizing the structure of the functional block copolymers and altering the ratio of the functional block copolymers. The blended GPx mimic exhibits remarkable catalytic activity and acts as a real catalyst with typical saturation kinetics behavior.

Reducibly degradable hydrogels of PNIPAM and PDMAEMA: Synthesis, stimulus-response and drug release

Reducibly degradable hydrogels of poly(N-isopropylacrylamide) (PNIPAM) and poly(N,N-dimethylaminoethyl methacrylate) (PDMAEMA) were synthesized by the combination of reversible addition-fragmentation chain transfer (RAFT) polymerization and click chemistry. The alkyne-pending copolymer of PNIPAM or PDMAEMA was obtained through RAFT copolymerization of propargyl acrylate with NIPAM or DMAEMA. Bis-2-azidyl-isobutyrylamide of cystamine (AIBCy) was used as the crosslinking reagent to prepare reducibly degradable hydrogels by click chemistry. The hydrogels exhibited temperature or pH stimulus-responsive behavior in water, with rapid response, high swelling ratio, and reproducible swelling/shrinkage cycles. The loading and release of ceftriaxone sodium proved the feasibility of the hydrogels as the stimulus-responsive drug delivery system. Furthermore, the presence of disulfide linkage in AIBCy favored the degradation of hydrogels in the reductive environment.

Synthesis and corrosion-protective properties of acetylenic esters of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

A procedure was developed for preparing acetylenic esters of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid. The structures of the compounds were confirmed by IR and 1H NMR spectroscopy. The Kovats indices of the compounds were determined, and their boiling points were estimated by gas-liquid chromatography. The protective properties of the esters against acid corrosion of steel were studied.

Preparation of block-brush PEG-b-P(NIPAM-g-DMAEMA) and its dual stimulus-response

Well-defined dually responsive block-brush copolymer of poly(ethylene glycol)-b-[poly(N-isopropylacrylamide)-g-poly(N,. N-dimethylamino-ethylmethacrylate)], [PEG-b-P(NIPAM-g-PDMAEMA)] was successfully prepared by the combination of atom transfer radical polymerization (ATRP) and click chemistry based on azide-capped PDMAEMA and alkyne-pending PEG-b-PNIPAM copolymer. Azide-capped PDMAEMA was synthesized through ATRP of DMAEMA monomer using an azide-functionalized initiator of β-azidoethyl-2-bromoisobutyrate. Alkyne-pending PEG-b-PNIPAM copolymer was obtained through ATRP copolymerization of NIPAM with propargyl acrylate. The final block-brush copolymer was synthesized by the click reaction between these two polymer precursors. Because of characteristics of three different blocks, the copolymer exhibited dually thermo- and pH-responsive behavior. The responsive behaviors of block-brush copolymer were studied by laser light scattering, temperature-dependent turbidity measurement and micro differential scanning calorimetry. The phase transition temperature of block-brush copolymer increased with the decrease of pH value. At pH = 5.0, the copolymer displayed weak thermo-responsive behavior and might form uni-molecular micelles upon heating. At higher pH values, the block-brush copolymer aggregated intermolecularly into the micelles during the phase transition.

Synthesis of polyfunctional triethoxysilanes by 'click silylation'

The copper-catalyzed 'click silylation' has been exploited for the chemical modification of γ-azidopropyltriethoxysilane (AzPTES) with a wide range of terminal alkynes (1a-1v) in a one-pot operation. The novel 1,2,3-triazole-triethoxysilane derivatives (2a-2v) were synthesized by this procedure and comprehensively characterized by IR spectra, 1H and 13C NMR, and HRMS studies.

Butatrien durch Thermolyse von Propiolsaeure-(2-propinyl)ester

Flow thermolysis of 2-propynyl propiolate (5) at 580 deg C afforded butatriene (6) (ca. 50percent) and as by-products, 4-methylene-2-cyclobuten-1-one (7), 2-ethynylpropenal (8), 1-penten-4-yn-3-one (9), 4-penten-2-ynal (10) (tottal ca. 10percent), along with some propynal, acetylene, CO2 and CO.In the same way, propiolic acid (1,1-D2)-2-propynyl propiolate (11) led to (1,1-D2)-butatriene (12) and a litle 4-((D2)methylene)-2-cyclobuten-1-one (13).A mechanism is proposed for the transformation of 5 into 6 and of 11 into 12, which also accounts for the formation of 7, 8, 9 and 10, as well as 13.The position of one of the published 13C-NMR signal of butatriene (6) must be revised.Thermolysis of methyl-(1) and ethyl propiolate (2) resulted in small yields of 2-buten-4-olide (3) and 2-penten-4-olide (4).

De Novo Design of Star-Shaped Glycoligands with Synthetic Polymer Structures toward an Influenza Hemagglutinin Inhibitor

Synthetic polymers with well-defined structures allow the development of nanomaterials with additional functions beyond biopolymers. Herein, we demonstrate de novo design of star-shaped glycoligands to interact with hemagglutinin (HA) using well-defined synthetic polymers with the aim of developing an effective inhibitor for the influenza virus. Prior to the synthesis, the length of the star polymer chains was predicted using the Gaussian model of synthetic polymers, and the degree of polymerization required to achieve multivalent binding to three carbohydrate recognition domains (CRDs) of HA was estimated. The star polymer with the predicted degree of polymerization was synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization, and 6′-sialyllactose was conjugated as the glycoepitope for HA. The designed glycoligand exhibited the strongest interaction with HA as a result of multivalent binding. This finding demonstrated that the biological function of the synthetic polymer could be controlled by precisely defining the polymer structures.

Synthesis of Functionalized 1,3-Butadienes via Pd-Catalyzed Cross-Couplings of Substituted Allenic Esters in Water at Room Temperature

An environmentally responsible, mild method for the synthesis of functionalized 1,3-butadienes is presented. It utilizes allenic esters of varying substitution patterns, as well as a wide range of boron-based nucleophiles under palladium catalysis, generating sp-sp2, sp2-sp2, and sp2-sp3 bonds. Functional group tolerance measured via robustness screening, along with room temperature and aqueous reaction conditions highlight the methodology's breadth and potential utility in synthesis.