6165-75-9

Usage

Uses

Propargyl benzenesulfonate is used as a general chemical reagent for organic syntheses due to its ability to participate in a wide range of chemical reactions, including cross-coupling, cyclization, and substitution reactions. Its unique reactivity allows it to be employed in the synthesis of various complex organic molecules.
Used in Pharmaceutical Industry:
Propargyl benzenesulfonate is used as a key intermediate in the manufacture of Omarigliptin, a DPP-4 (dipeptidyl peptidase-4) inhibitor. Omarigliptin is an oral antihyperglycemic agent used in the treatment of type-2 diabetes. It works by inhibiting the DPP-4 enzyme, which in turn increases the levels of insulin and decreases the levels of glucagon, helping to regulate blood sugar levels in patients with type-2 diabetes.

InChI:InChI=1/C9H8O3S/c1-2-8-12-13(10,11)9-6-4-3-5-7-9/h1,3-7H,8H2

Upstream product

• 107-19-7 propargyl alcohol 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 17061-85-7 1-nitro-4-(prop-2-ynyloxy)benzene 
• 26557-77-7 N-(4-(prop-2-yn-1-yloxy)phenyl)acetamide 
• 18158-68-4 N,N-di(prop-2-yn-1-yl)aniline 
• 20009-28-3 naphth-2-yloxymethylacetylene 
• 13350-09-9 1-nitro-2-(prop-2-yn-1-yloxy)benzene 
• 13610-02-1 1-phenoxy-2-propyne 
• 24309-48-6 propargyl thiocyanate 
• 92428-77-8 Dithiophosphorsaeure-O,O--S- 
• 90537-10-3 Benzolsulfonsaeure-<2.2.3.3-tetrabrom-propylester> 
• 14445-61-5 trans-Benzolsulfonsaeure-<2.3-dibrom-propen-(2)-ylester> 
• 14445-62-6 cis-Benzolsulfonsaeure-<2.3-dibrom-propen-(2)-ylester> 
• 22774-64-7 N-propargyl-4-methylaniline 
• 22774-67-0 4-chloro-N-prop-2-ynylaniline 
• 22774-35-2 4-chloro-N,N-di(prop-2-ynyl)benzenamine 

Relevant academic research and scientific papers

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.

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 synthesis method of prop-2-yn-1-yl benzenesulfonate

The invention discloses a green synthesis method of prop-2-yn-1-yl benzenesulfonate. The method is characterized in that benzene sulfonyl chloride and propargyl alcohol are taken as raw materials, a reaction is promoted by taking inorganic base as an acid capture agent in an aqueous phase, so as to obtain a high-purity target product; the method has the advantages that the related reaction conditions are mild, the yield is high, operation is simple and convenient, the green and environmental protection effects are realized, and large-scale production is promoted.

Synthetic method of benzenesulfonate derivative

The invention relates to a synthetic method of a benzenesulfonate derivative and belongs to the technical field of synthesis of compounds. A compound (described in the specification) is taken as raw materials, and reaction is carried out with ethylene glycol or R2-OH to generate a compound (described in the specification), wherein R1 is selected from alkyl, H or F, and R2 is selected from allyl, propargyl or benzene. The synthetic method provided by the invention comprises the following concrete operations: adding ethylene glycol or R2-OH and dichloromethane into a reactor, adding organic alkali while stirring, then cooling to the temperature below 15 DEG C, starting to dropwise add a substance (described in the specification), after the substance is dropwise added, returning to room temperature and further stirring for 0.5-1 hour, then heating and carrying out reflux reaction for 1-2 hours, after the reflux reaction is complete, carrying out ice thawing treatment, layering, drying, and concentrating, so that the benzenesulfonate derivative product is obtained. The synthetic method provided by the invention is simple, reaction process is mild and stable, yield is high, and the obtained product is high in purity.

PROCESS FOR THE PREPARATION OF ENATIOMERICALLY PURE 1-AMINOINDAN

The present invention relates to a process for the preparation of optically pure ( R) -1-aminoindan by a diastereomeric resolution of 1-aminoindan using N-acetyl-L-glutamic acid as a resolving agent. In another aspect, the invention relates to diastereomeric salts of (R) -1-aminoindan with N-acetyl-L-glutamic acid, and their use in the process for the preparation of rasagiline.

Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds

This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.

KINETICS AND MECHANISM OF AMINOLYSIS OF PROPARGYL AND 1-METHYL-PROPARGYL ARENESULPHONATES

Kinetic studies were carried out on the aminolysis of propargyl and 1-methylpropargyl arenesulphonates in acetonitrile at 45.0 deg C.The cross-interaction constants, ρxz and βxz, are similar to, but smaller than, those for the SN2 processes at other primary and secondary carbon centers.Compared with the allyl series, the smaller magnitude of ρxz and βxz reflects a looser transition state, which in turn leads to a lower rate despite the greater Taft's ?* value and the lower intrinsic (ΔE0) and thermodynamic barriers (ΔE0).