6165-76-0

Usage

Uses

Propargyl p-toluenesulfonate is used as a crucial raw material and intermediate in the fields of organic synthesis, pharmaceuticals, agrochemicals, and dyestuff. Its applications span across different industries due to its unique chemical properties and reactivity.
Used in Organic Synthesis:
Propargyl p-toluenesulfonate is used as a key intermediate for the synthesis of various organic compounds. It is particularly useful in the formation of linear and cyclic poly(2-isopropyl-2-oxazoline)s through cationic ring-opening polymerization of 2-isopropyl-2-oxazoline.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Propargyl p-toluenesulfonate is utilized as a reagent for the synthesis of 2-hydroxy-4-pentynoic acid. This is achieved through a series of alkylation, hydrolysis, decarboxylation, diazotization, and hydroxylation reactions with diethyl 2-acetamidomalonate.
Used in Agrochemicals:
Propargyl p-toluenesulfonate is employed in the agrochemical industry as a starting material for the development of new agrochemical products. Its unique chemical properties make it a valuable component in the creation of innovative and effective solutions for agricultural applications.
Used in Dyestuff Industry:
In the dyestuff industry, Propargyl p-toluenesulfonate is used as an intermediate for the production of various dyes. Its reactivity and versatility allow for the development of a wide range of colorants with different properties and applications.
Used in the Synthesis of Furan Derivatives:
Propargyl p-toluenesulfonate can also be used as a reagent in the synthesis of furan derivatives through a Pd-catalyzed reaction with acylchromates. This application highlights its importance in the development of novel chemical compounds with potential applications in various industries.

InChI:InChI=1/C10H10O2S/c1-3-8-13(11,12)10-6-4-9(2)5-7-10/h1,4-7H,8H2,2H3

Upstream product

• 107-19-7 propargyl alcohol 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 5651-91-2 1,2-bis(prop-2-ynyloxy)benzene 
• 6088-94-4 nona-1,4-diyne 
• 10420-91-4 hexadiyne-1,4 
• 42066-39-7 1,3-di-tert-butylallene 
• 71789-10-1 1-trimethylsilyl-1,4-pentadiyne 
• 22774-64-7 N-propargyl-4-methylaniline 
• 75169-12-9 2,6-Di-tert-butyl-4-prop-2-ynyloxy-phenol 
• 406-40-6 4,4,4-trifluorobuta-1,2-diene 
• 6088-96-6 (penta-1,4-diynyl)benzene 
• 118724-05-3 (1H-[1,2,3]triazol-4-yl)methanamine 
• 141362-48-3 Benzyl 2(S)-<(tert-butoxycarbonyl)amino>hexa-4,5-dienoate 
• 14465-74-8 N-phenyl-N-prop-2-ynylamine 
• 14034-57-2 anilinium p-tolylsulfonate 
• 1027837-67-7 4-(1-prop-2-ynyl-piperidin-4-ylmethyl)-phenol 

Relevant academic research and scientific papers

An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards 'clickable' biodegradable polylactide

2-Hydroxy-4-pentynoic acid (1) is a key intermediate towards 'clickable' polylactide which allows for efficient introduction of a broad range of pendant functional groups onto polymers from a single monomer via convenient 'click' chemistry with organic az

A chemical labeling of N6-formyl adenosine (f6A) RNA

N6-methyl adenosine (m6A) is an eminent epigenetic mark in mRNAs that affects a broad range of biological functions in diverse species. However, the chemically inert methyl group prevents a direct labeling of this modification for subsequent detection and sequencing. Therefore, most current approaches for the labeling of m6A still have limitations of relying on the utilization of corresponding methyltransferases, which resulted in the lacking of efficiency. Here we present an approach which selectively alkylated the N6-formyl adenosine (f6A), the key intermediate during chemical oxidation of m6A, with an alkyne functionality that can be further labeled with click reactions. This covalent labeling approach will be able to facilitate in the affinity purification, detection and genome-wide profiling studies.

Green one-pot four-component synthesis of 3,5-disubstituted isoxazoles- sulfonates and sulfonamides using a combination of NaDCC as metal-free catalyst and ultrasonic activation in water

A simple and green one-pot reaction has been proposed for the synthesis of novel 3,5-disubstituted isoxazole-sulfonates and -sulfonamides (5a-j) in water under ultrasound irradiation. The methodology is based on the use of safe and environmentally friendly reagents and allows, via in-situ 1,3-dipolar cycloaddition, an easy access to functionalized heterocycles with the creation of four new bonds (S[sbnd]O, C[sbnd]N, C[sbnd]O and C[sbnd]C). Comparison studies using classical magnetic stirring and ultrasound irradiation clearly showed that sonication promoted clean transformation, high yields (72–89%) and faster reactions (20–28 min). All the synthesized compounds were fully characterized by MS-ES, 1H NMR, 13C NMR spectroscopy and HPLC analysis.

Synthesis of fish scale derived hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for highly efficient synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as antifungal agents

Abstract: The preparation, characterization and application of hydroxyapatite silica propyl bis aminoethoxy ethane cuprous complex (HASPBAEECC) as a novel hybrid nano-catalyst for synthesis of new benzimidazole-1,2,3-triazole hybrid analogues as promising

Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry

Influenza is a major threat to millions of people worldwide. Entry inhibitors are of particular interest for the development of novel therapeutic strategies for influenza. We have previously discovered oleanolic acid (OA) to be a mild influenza hemagglutinin (HA) inhibitor. In this work, inspired by the 3D structure of HA as a homotrimeric receptor, we designed and synthesized 15 OA trimers with different linkers and central region via the copper-catalyzed azide-alkyne cycloaddition reaction. All of the OA trimers were evaluated for their antiviral activities in vitro, and 12c, 12e, 13c, and 13d were observed to exhibit robust potency (IC50 in the submicromolar range) against influenza A/WSN/33 (H1N1) virus that was stronger than that observed with oseltamivir. In addition, these compounds also displayed strong biological activity against A/Hong Kong/4801/2014 and B/Sichuan/531/2018 (BV). The results of hemagglutination inhibition assays and surface plasmon resonance binding assays suggest that these OA trimers may interrupt the interaction between the HA protein of influenza virus and the host cell sialic acid receptor, thus blocking viral entry. These findings highlight the utility of multivalent OA conjugates to enhance the ligand-target interactions in anti-influenza virus drug design and are also helpful for studying antiviral drugs derived from natural products.

Synthetic method of oxadiargyl (by machine translation)

The invention discloses a synthetic method, of oxadiargyl, in a non-protonic organic solvent, oxadone phenol is subjected to filtration, distillation to remove the solvent, and then the synthesis method disclosed by the invention is suitable for industrial application, without the addition of the catalyst. with a flammable, explosive chlorine propyne or bromopropyne raw material, in the presence of a catalyst . The synthetic method disclosed by the invention does not need, to be added with a flammable and explosive compound . The synthetic method is suitable for industrial. application. (by machine translation)

Silica-tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano-catalyst for highly efficient synthesis of new 1,2,3-triazolyl-based metronidazole hybrid analogues having potent antigiardial activity

The preparation, characterization and application of silica-tethered cuprous acetophenone thiosemicarbazone (STCATSC) as a novel hybrid nano catalyst for synthesis of new 1,2,3-triazolyl-based metronidazole hybrid analogues is described. STCATSC is fully

Luminescent iridium(iii) complexes of N-heterocyclic carbene ligands prepared using the 'click reaction'

A series of imidazolium salt, N-heterocyclic carbene (NHC) ligand precursors, combined with 1,2,3-triazoles were synthesized using the Cu(i) catalyzed azide-alkyne cycloaddition 'click reaction'. These pro-ligands were prepared from imidazolium molecules that were functionalized with either a terminal alkyne or azide group. Methylation of the triazole unit with methyl iodide produced a series of imidazolium/triazolium NHC pro-ligands. From these pro-ligands a family of luminescent Ir(iii) complexes of the general form [Ir(ppy)2(C^N)]+ or [Ir(ppy)2(C-C)]+ (where ppy is 2-phenylpyridine and C-N represents a bidentate imidazolylidene/triazole ligand and C-C represents a bidentate imidazolylidene/triazolylidene ligand) were prepared. The electrochemical, photophysical and electrochemiluminescence properties of the complexes have been evaluated and a preliminary study of two of these compounds as luminescent probes for cell imaging studies was conducted in A549 human lung adenocarcinoma basal epithelial cells. Co-localisation studies with the commercial dye MitoTracker CMXRos were consistent with mitochondrial uptake for these compounds.

Design, synthesis, and in silico studies of novel eugenyloxy propanol azole derivatives having potent antinociceptive activity and evaluation of their β-adrenoceptor blocking property

The design, synthesis, antinociceptive and β-adrenoceptor blocking activities of several eugenyloxy propanol azole derivatives have been described. In this synthesis, the reaction of eugenol with epichlorohydrin provided adducts 3 and 4 which were N-alkylated by diverse azoles to obtain the eugenyloxy propanol azole analogues in good yields. Adducts 3 and 4 were also reacted with azide ion to obtain the corresponding azide 6. The ‘Click’ Huisgen cycloaddition reaction of 6 with diverse alkynes afforded the title compounds in good yields. The synthesized eugenyloxy propanol azole derivatives were in vivo studied for the acute antinociception on male Spargue Dawley rats using tail-flick test. Compounds 5f, 5g, 7b and 11a exhibited potent analgesic properties in comparison with eugenol as a standard drug. In addition, all compounds were ex vivo tested for β-adrenoceptor blocking properties on isolated left atrium of male rats which exhibited partial antagonist or agonist behaviour compared to the standard drugs. The molecular docking study on the binding site of transient receptor potential vanilloid subtype 1 (TRPV1) has indicated that like capsaicin, eugenyloxy propanol azole analogues exhibited the strong affinity to bind at site of TPRV1 in a “tail-up, head-down” conformation and the presence of triazolyl moieties has played undeniable role in durable binding of these ligands to TRPV1. The in silico pharmacokinetic profile, drug likeness and toxicity predictions carried out for all compounds determined that 5g can be considered as potential antinociceptive drug candidate for future research.

Synthesis and Reactivity of N-Allenyl Cyanamides

N-Allenyl cyanamides have been accessed via a one-pot deoxycyanamidation-isomerization approach using propargyl alcohol and N-cyano-N-phenyl-p-methylbenzenesulfonamide. The utility of this novel class of allenamide was explored through derivatization, with hydroarylation, hydroamination, and cycloaddition protocols employed to access an array of cyanamide products that would be challenging to access using existing methods.