16836-95-6

Usage

Uses

Used in Organic Synthesis:
Silver p-toluenesulfonate is used as a reagent for the conversion of alkyl halides to alkyl tosylates. This application is particularly useful in organic synthesis, as it allows for the formation of new chemical bonds and the creation of a variety of complex molecules.
Used in Promotion of Leaving Ability of Halogens:
Silver p-toluenesulfonate is also used to enhance the leaving ability of halogens in chemical reactions. This property makes it a valuable tool in the synthesis of various organic compounds, as it can facilitate the formation of new bonds and improve the overall efficiency of the reaction.
Used in the Conversion of Benzyl Selenyl Chlorides:
In addition to its use with alkyl halides, silver p-toluenesulfonate is also used in the conversion of benzyl selenyl chlorides into their corresponding selenyl tosylates. This application further demonstrates the versatility of this reagent in organic synthesis, as it can be applied to a range of different chemical reactions and transformations.

Purification Methods

The anhydrous salt is obtained by recrystallisation from H2O. Store it in the dark. [Claesson & Wallin Chem Ber 12 1851 1879, Beilstein 11 H 97, 99.]

InChI:InChI=1/C7H8O3S.Ag/c1-6-2-4-7(5-3-6)11(8,9)10;/h2-5H,1H3,(H,8,9,10);/q;+1/p-1

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 20667-12-3 silver(l) oxide 
• 16106-44-8 potassium tosylate 

Downstream Products

• 24124-59-2 methylene ditosylate 
• 433-10-3 4-fluorobutyl tosylate 
• 122596-11-6 1,1,4,4-tetramethyl-piperazinediium; bis-(toluene-4-sulfonate) 
• 1024-41-5 benzyl tosylate 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 6315-52-2 1,2-bis-tosyloxyethane 
• 70008-07-0 1-O-tosyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose 
• 80-48-8 methyl p-toluene sulfonate 
• 51761-40-1 C₁₁H₁₇O₅PS 
• 2342-67-8 3,3,3-trifluoropropyl-4-methylbenzene sulphonate 
• 51761-41-2 C₁₃H₂₁O₅PS 
• 13294-36-5 C₁₁H₁₆O₅S₂ 
• 51761-42-3 O,O'-dibutyl-phosphorous toluene-4-sulfonic anhydride 
• 54619-27-1 2-hydroxy-1-methylethyl 4-toluenesulfonate 

Relevant academic research and scientific papers

Nonaqueous preparation of stable silver nanoparticles dispersions from organic sulfonic acids

The conditions for stable silver nanoparticles dispersions synthesis from organic sulfonic acids in an anhydrous medium of ethylene glycol and its methyl ester were studied. Ascorbic acid and potassium citrate were used as reducing agents.

Impact of counterions on micelle formation and polymerization of 11-acryloyloxyundecyltrimethylammonium surfactants

New surfactants based on the cationic monomer 11-acryloyloxyundecyltrimethylammonium with counterions bromide, nitrate, acetate, camphorsulfonate, 4-toluenesulfonate, trifluoroacetate were obtained in this work. In most cases counterions change the critical micelle concentration by 2–3 times (being compared with bromide) except sample with acetate counterions (in this case critical micelle concentration increases by an order of magnitude). Substitution of bromide for hydrophobic counterions (toluenesulfonate, trifluoroacetate, camphorsulfonate) does not lead to expected transformation of spherical micelles to long wormlike micelles. The polymerization of such monomers occurs according to the microemulsion mechanism involving micelles of monomers.

An unusual diverse coordination of silver(I) with N-allylthiohydantoin ligand in the presence of benzene- and p-toluenesulfonate anions

Crystalline silver(I) coordination compounds [Ag2(HL)4(C6H5SO3)2]·0.5C3H7OH (1) and [Ag2(HL)(L)(CH3C6H4SO3)] (2) (HL = 3-(prop-2-en-1-yl)-2-thioxoimidazolidin-4-one) have been obtained using silver(I) salts and the organic ligand HL. Three independent Ag(I) atoms in crystal 1 adopt exclusively different coordination environment: tetragonal pyramidal, seesaw and distorted tetrahedral. In crystal 2 metal ions coordination polyhedra are characterized by seesaw and distorted tetrahedral arrangements. Thiohydantoin molecules in both structures are attached to Ag(I) only through thiohydantoin S-atom, while its anionic form in 2 plays a role of N,S-linker. C6H5SO3? anions in 1 are bound to the Ag(I) ions in a bridging mode, connecting silver ions into serpentine-like {Ag4(C6H5SO3)4}n chains, within which silver ions are additionally bind with μ2-S atoms of HL. Simultaneous coordination of HL and L? moieties in polymeric chains of 2 allow the formation of Ag….Ag metallophilic interactions with the distance range of 2.99–3.13 ?.

A new two-dimensional AgI coordination polymer with Ag?C interactions: Thermal, fluorescence, structural and solution studies

A 2D polymer with Ag?C interactions, [Ag(μ5-TS)]n (1) [TS- = toluene-4-sulfonate], has been synthesized and characterized and its structure was determined by X-ray crystallography. In addition to coordination of the O atoms of TS-, the Ag atoms also form weak η1 Ag?C interactions. The thermal stability of 1 was studied by thermal gravimetric (TG) and differential thermal analyses (DTA). The ligand and compound 1 are luminescent in DMF, with emission maxima at 358 and 335, respectively. Solution studies of complex 1 were done in DMF and in CH3CN.

18F-Labeled Derivatives of Irbesartan for Angiotensin II Receptor PET Imaging

The renin angiotensin aldosterone system (RAAS) is a hormonal cascade involved in the regulation of blood pressure and electrolyte balance, and represents a common target for the treatment of various diseases including hypertension, heart failure, and diabetes. Herein we present a novel 18F-labeled derivative of the drug irbesartan, one of the most prescribed angiotensin II type 1 receptor (AT1R) antagonists, for in vivo positron emission tomography (PET). This allows the in vivo measurement of AT1R expression, and thus the evaluation of functional changes in its expression under pathophysiological conditions. We followed various synthetic approaches optimized for the introduction of fluorine into different positions of the aliphatic side chain of irbesartan. Radioligand binding studies revealed that fluorine atoms at specified positions (α-position (IC50=6.6 nm) and δ-position (IC50=8.5 nm) of the aliphatic side chain) do not alter the binding properties of irbesartan (IC50=1.6 nm). After successful radiolabeling with fluorine-18 in a radiochemical yield of 11 %, we observed high renal uptake in healthy rats and pigs, which could be decreased by pretreatment with the parent compound irbesartan.

MANUFACTURING METHOD OF FLUORINATED HYDROCARBON

PROBLEM TO BE SOLVED: To provide a method for industrially advantageously manufacturing fluorinated hydrocarbon (3). SOLUTION: There is provided a method for manufacturing fluorinated hydrocarbon represented by the formula (3), including contacting a secondary or tertiary ether compound represented by the formula (1) and acid fluoride represented by the formula (2) in the presence of a silver salt in a hydrocarbon solvent. R1 and R2 are each independently a C1 to 3 alkyl group, R1 and R2 may bind to form a ring structure, R3 is H, a methyl group or an ethyl group, R4 and R5 are each independently a methyl group or an ethyl group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Fluorine-containing 6,7-dialkoxybiaryl-based inhibitors for phosphodiesterase 10 A: Synthesis and in vitro evaluation of inhibitory potency, selectivity, and metabolism

Based on the potent phosphodiesterase 10 A (PDE10A) inhibitor PQ-10, we synthesized 32 derivatives to determine relationships between their molecular structure and binding properties. Their roles as potential positron emission tomography (PET) ligands were evaluated, as well as their inhibitory potency toward PDE10A and other PDEs, and their metabolic stability was determined in vitro. According to our findings, halo-alkyl substituents at position 2 of the quinazoline moiety and/or halo-alkyloxy substituents at positions 6 or 7 affect not only the compounds′ affinity, but also their selectivity toward PDE10A. As a result of substituting the methoxy group for a monofluoroethoxy or difluoroethoxy group at position 6 of the quinazoline ring, the selectivity for PDE10A over PDE3A increased. The same result was obtained by 6,7-difluoride substitution on the quinoxaline moiety. Finally, fluorinated compounds (R)-7-(fluoromethoxy)-6-methoxy-4-(3-(quinoxaline-2-yloxy)pyrrolidine-1-yl) quinazoline (16 a), 19 a-d, (R)-tert-butyl-3-(6-fluoroquinoxalin-2-yloxy) pyrrolidine-1-carboxylate (29), and 35 (IC50 PDE10A 11-65 nM) showed the highest inhibitory potential. Further, fluoroethoxy substitution at position 7 of the quinazoline ring improved metabolic stability over that of the lead structure PQ-10. Fluor your health: Phosphodiesterase 10 A (PDE10A) has emerged as an attractive target for the development of 18F-labelled brain imaging agents for positron emission tomography. A series of fluorinated dialkoxybiaryl compounds were synthesized and evaluated as PDE10A inhibitors, assisted by QSAR docking studies. The 7-fluoromethoxy derivative appears to be a promising candidate for further development.

Gold(I) complexes of conformationally constricted chiral ferrocenyl phosphines

The preparation of two new chiral, enantiopure, and conformationally constrained phosphocin and 1,5-diphosphocin, incorporating two ferrocenyl units, is described. The gold(I) chloride complexes of these ligands and (S)-(R)-PPF-OMe were prepared, and their structures, in solution and solid states, are compared. Abstraction of the chloride anion by the addition of silver salt of either toluenesulfonate or chiral BINOL-phosphates generates active catalysts for the intramolecular cyclization of 6-methyl-1,1- diphenylhepta-4,5-dien-1-ol, where up to 47% ee can be obtained. Match and mismatch effects between chiral ligands and counteranions are highlighted.

Facile synthesis of effcient and selective ruthenium olefin metathesis catalysts with sulfonate and phosphate ligands

A series of novel, air-stable ruthenium NHC catalysts with sulfonate and phosphate anions have been prepared easily in one pot at high yields using commercially available precursors. The catalysts were found to be effective for ring-opening metathesis polymerization, ring-closing metathesis, and cross-metathesis. The catalysts showed higher cis-selectivity in olefin cross-metathesis reactions as compared to earlier known ruthenium-based olefin metathesis catalysts, with allylbenzene and cis-1,4-diacetoxybutene as substrates.

Quaternary xanthinylalkyl nortropine

There are prepared quaternary xanthinylalkylnortropine derivatives of the general formula I STR1 where T represents a theophyllinyl-7 radical or a theobrominyl-(1)-radical, Alk is a straight or branched chain alkylene group having 2 to 10 carbon atoms or such a group substituted by a hydroxyl group, R is an alkyl group of 1 to 4 carbon atoms and A(-) is an equivalent to an anion of a physiologically compatible mono- or polyvalent acid. The compounds are useful as medicines having a spasmolytic activity.