627-09-8

Usage

Uses

Used in Pharmaceutical Industry:
Propargyl acetate is used as a key intermediate for the synthesis of optically active γ-hydroxy α,β-unsaturated aldehydes, which are important in the development of pharmaceuticals with chiral centers. These aldehydes are crucial in the production of various drugs, including those used to treat chronic diseases and conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, propargyl acetate is used as a starting material for the production of homopropargyl alcohols. These alcohols are valuable building blocks in the synthesis of complex organic molecules, such as natural products and bioactive compounds, which have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Polymer Science:
Propargyl acetate is also used in polymer science for the synthesis of poly(propargyl acetate), a specialty polymer with unique properties. This polymer has potential applications in various fields, such as coatings, adhesives, and composite materials, due to its thermal stability, mechanical strength, and chemical resistance.

InChI:InChI=1/C5H6O2/c1-3-4-7-5(2)6/h1H,4H2,2H3

Upstream product

• 107-19-7 propargyl alcohol 
• 75-36-5 acetyl chloride 
• 74-99-7 prop-1-yne 
• 127-09-3 sodium acetate 
• 106-96-7 propargyl bromide 
• 64-19-7 acetic acid 
• 26755-52-2 propargyl monobromoacetate 
• 141-78-6 ethyl acetate 
• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 17869-81-7 methoxy(prop-2-yn-1-yloxy)methane 
• 108-24-7 acetic anhydride 
• 1067-60-3 triethyl-prop-2-ynyloxy-stannane 

Downstream Products

• 116977-29-8 3-acetoxy-1-acetylsulfanyl-propene 
• 59051-15-9 1-acetoxy-2,3-bis-acetylsulfanyl-propane 
• 69337-36-6 acetic acid (3-phenyl-5-isoxazolyl)methyl ester 
• 91356-02-4 Dimethyl-<1-isopropyl-3-acetoxymethyl-2-propin-1-yl>-amin 
• 59192-73-3 1-Acetoxy-5-cyclohexyliden-pent-4-en-2-in 
• 137513-39-4 Acetic acid (E)-4-hydroxy-4-methyl-6-phenyl-hex-2-enyl ester 
• 84920-35-4 3-methyl-1-phenylhexa-4,5-dien-3-ol 
• 84920-36-5 3-methyl-1-phenylhex-5-yn-3-ol 
• 115261-70-6 Acetic acid 5,6-diphenyl-[1,4]dithiin-2-ylmethyl ester 
• 2327-99-3 1-phenylpropadiene 
• 10147-11-2 propargyl benzene 
• 52071-96-2 (Z)-3-phenylthio-2-propenyl acetate 
• 52071-97-3 (E)-3-phenylthio-2-propenyl acetate 
• 3921-94-6 4-(dimethylamino)but-2-yn-1-yl acetate 

Relevant academic research and scientific papers

Cis and trans radicals generated in helical poly(propargyl acetate)s prepared using a [Rh(norbornadiene)Cl]2 catalyst

The poly(propargyl acetate) (A) having a helical cis-transoid structure was stereospecifically prepared using the Rh complex catalyst, [Rh(norbornadiene) Cl]2, in MeOH or NEt3 solvent at 0 and 40 °C in moderate yield. Electron spin resonance (ESR) analysis of the polymer revealed the formation of the cis (B) and trans (C) radicals which were produced through the thermal rotational scission of the helical cis CC bonds in the main-chain during the polymerization. The spatial and geometrical structure was successfully deduced using the two analogues' polymers in which either methyl or methylene group is deuterated, by the aide of computer simulation of the observed ESR spectra together with the calculation of spin density of the two radicals.

Simple One-Pot Preparation of 1,2-Diacetoxy-2-propene. A Convenient Precursor of 1-Acetoxy-3-chloro-2-propanone

From a neat mixture of acetic acid and propargyl alcohol, 1,2-diacetoxy-2-propene was prepared by successive treatment with an acid catalyst and a Ru catalyst in one-pot procedure.The product was a convenient precursor of 1-acetoxy-3-chloro-2-propanone.

Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst

A novel and highly enantioselective synthesis of hydroxyalkynyl esters and ethers through the asymmetric addition of alkynyl esters or ethers to aldehydes promoted by a cyclopropyl amino alcohol based zinc catalyst has been developed. The method afforded a library of new enantioenriched hydroxyalkynol esters and ethers (up to 93percent yield; 95percent ee), and it was compatible with a broad range of functional groups. Moreover, it could be used in the synthesis of carbon-chain-elongated enantioenriched hydroxyalkynol esters and (2 R,5 R)-musclide-A1, a cardiotonic potentiating principle from musk.

Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles

Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).

Rhodium-catalysed synthesis of fused pyrimidine derivatives employing N-sulfonyl-1,2,3-triazoles as a 1-aza-[4C] synthon

A new synthetic application of N-sulfonyl-1,2,3-triazoles acting as a 1-aza-[4C] synthon via the 1,2-shift reaction of an α-imine rhodium carbene was developed for the synthesis of fused pyrimidine derivatives. The high reactivity of the strained three-me

Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition

A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).

Deep eutectic solvent choline chloride·2CrCl3·6H2O: An efficient catalyst for esterification of formic and acetic acid at room temperature

A highly efficient and selective method for esterification of formic and acetic acid with alcohols has been achieved at room temperature, with the choline chloride (ChCl)/chromium(iii) chloride hexahydrate (CrCl3·6H2O) deep eutectic solvent as a catalyst. High yields and good selectivities of organic esters are obtained using DES [ChCl][CrCl3·6H2O]2 with the molar ratio 5:1 (carboxylic acids:alcohols) at room temperature in 24 h. The ease of recovery and reusability of DES with high catalytic activity makes this method efficient and practical.

PROCESS FOR THE PREPARATION OF HYPERPOLARIZED CARBOXYLATE COMPOUNDS

The present invention relates to a process for the preparation of aqueous solutions of [1-13C]-hyperpolarized carboxylate containing molecules of diagnostic interest that comprises parahydrogenating with molecular parahydrogen unsaturated alkenyl or alkynyl esters of the concerned 13C- carboxylate molecules.

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.

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.