6165-76-0

Basic information

• Product Name: Propargyl p-toluenesulfonate
• Synonyms: prop-2-ynyl 4-methylbenzenesulfonate;Propargyl p-toluenesulfonate >=97.0% (GC);PROPARGYL P-TOLUENESULFONATE;PROPARGYL TOSYLATE;PROPARGYL P-TOLUENESULPHONATE;P-TOLUENESULFONIC ACID PROPARGYL ESTER;2-propyn-1-ol,4-methylbenzenesulfonate;p-toluenesulfonicacid,2-propynylester
• CAS NO: 6165-76-0
• Molecular Formula: C₁₀H₁₀O₃S
• Molecular Weight: 210.25
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives;Organic Building Blocks;Sulfur Compounds;Tosylates
• Mol File: 6165-76-0.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 117-121°C 0,3mm
• Flash Point: 117-121°C/0.3mm
• Appearance: Clear colorless to brown/Liquid
• Density: 1.215 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000135mmHg at 25°C
• Refractive Index: n20/D 1.530
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in Chloroform, Dichloromethane, DMSO, Ethyl Acetate. Not miscible in water.
• BRN: 1212957
• CAS DataBase Reference: Propargyl p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Propargyl p-toluenesulfonate(6165-76-0)
• EPA Substance Registry System: Propargyl p-toluenesulfonate(6165-76-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: XT7300000
• F: 4.10-10-21
• Hazardous Substances Data: 6165-76-0(Hazardous Substances Data)

Usage

Description

Propargyl p-toluenesulfonate, also known as 4-(prop-2-ynyl)benzenesulfonic acid p-toluenesulfonate, is an organic compound that serves as a versatile intermediate in various chemical reactions. It is characterized by its clear colorless to brown liquid appearance and is known for its reactivity in organic synthesis.

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

• 56620-43-0 3-isocyanatoprop-1-yne 
• 106-96-7 propargyl bromide 
• 2450-71-7 Propargylamine 
• 5651-91-2 1,2-bis(prop-2-ynyloxy)benzene 
• 13105-77-6 2-(N-prop-2-ynyl-anilino)-ethanol 
• 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 
• 6323-87-1 N,N-diisopropylprop-2-yn-1-amine 
• 14465-74-8 N-phenyl-N-prop-2-ynylamine 
• 24442-69-1 malononitrile 
• 75169-12-9 2,6-Di-tert-butyl-4-prop-2-ynyloxy-phenol 

Relevant articles and documents

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

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.

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.