80-41-1

Usage

Uses

Used in Chemical Synthesis:
2-Chloroethyl p-Toluenesulfonate is used as a reactant for the synthesis of triphenylethanamine derivatives and fluorinated carbazole derivatives, which are important compounds in various chemical and pharmaceutical applications.
Used in Analytical Chemistry:
2-Chloroethyl p-Toluenesulfonate has been used to develop a method for the determination of a variety of hydrophobic aromatic sulfonates by micellar electrokinetic chromatography, a technique used for the separation and analysis of charged species in complex mixtures.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 5783, 1988 DOI: 10.1021/jo00259a035

InChI:InChI=1/C9H11ClO3S/c1-8-2-4-9(5-3-8)14(11,12)13-7-6-10/h2-5H,6-7H2,1H3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 107-07-3 2-chloro-ethanol 
• 13891-58-2 chloroethyl chlorosulfate 
• 108-88-3 toluene 
• 75-21-8 oxirane 
• 74-85-1 ethene 
• 7182-86-7 tetrabutylammonium p-toluenesulfonate 
• 107-04-0 1-Bromo-2-chloroethane 
• 80-48-8 methyl p-toluene sulfonate 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 35006-61-2 (4-chlorobut-1-yn-1-yl)benzene 
• 39199-37-6 2-(2-methylphenyl)-1-chloroethane 
• 20764-35-6 1-chloro-2-(p-methyl)phenoxyethan 
• 21786-08-3 10-(2-chloroethyl)-10H-phenothiazine 
• 622-24-2 2-phenylethyl chloride 
• 17210-75-2 2-chloro-10-(2'-chloroethyl)-10H-phenothiazine 
• 51251-55-9 2-(naphthalen-1-yloxy)ethyl chloride 
• 128988-95-4 (2-chloro-ethyl)-(2-methyl-5-nitro-phenyl)-ether 
• 36616-28-1 2-(4-acetamidophenoxy)ethyl chloride 
• 99860-18-1 2-(2-chloro-ethoxy)-4-nitro-benzoic acid ethyl ester 
• 100542-23-2 4-bromo-benzenesulfonic acid-[4-chloro-N-(2-chloro-ethyl)-anilide] 
• 857005-58-4 toluene-4-sulfonic acid-[N-(2-chloro-ethyl)-4-(4-nitro-phenylsulfanyl)-anilide] 
• 77200-24-9 1-(2-chloroethyl)-1H-pyrrole 
• 607-26-1 N,N'-ethylenediphthalimide 

Relevant academic research and scientific papers

Fluorescent molecule for recognizing copper ions, preparation method and application

The invention discloses a fluorescent molecule for recognizing copper ions, a preparation method and application. Polycyclic aromatic hydrocarbons such as naphthalene rings or anthracene rings are used as initial raw materials; through a series of optimized organic synthesis reaction (substitution and addition), after the connection with different recognition sites, molecular clamp body tweezer host compounds with different recognition performance can be obtained. The fluorescent molecule can be used for copper ion detection and solves the problems that the existing molecule device is difficult to effectively recognize object molecules.

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

An alternative method for forming sulfonates through hypervalent iodine(III) reagent-mediated oxidation of sodium sulfinates has been developed. This transformation involves trapping reactive sulfonium species using alcohols. With additional optimization of the reaction conditions, the method appears extendable to other nucleophiles such as electron-rich aromatic systems or cyclic ethers through a ring opening pathway.

BENZIMIDAZOLES AND RELATED ANALOGS AS SIRTUIN MODULATORS

Provided herein are sirtuin-modulating compounds of formula (II) The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

FUNCTIONALIZED POLYMERS USING PROTECTED THIOLS

A process for the preparation of functional molecules using the thiol-ene coupling reaction and a process for the preparation of protected functional thiols, specifically thioesters is provided. The methods may be used to make functional polymers and other molecules. The method of making a functionalized polymer using a thiol-ene reaction comprises: providing a functionalized thioester having the following formula: (I) wherein R is a functional group and COR' is a protecting group; cleaving the functionalized thioester, forming a functional thiol and an acyl group; providing a polymer having a pendant vinyl group; and reacting the polymer with the functional thiol whereby a functionalized polymer is formed, wherein the functional thiol is not isolated prior to reacting with the polymer.

[2]Catenane Assembly from Calix[4]arene Crown Ethers

A variety of novel calix[4]arene-incorporating crown ethers with or without intramolecular hydrogen bonding have been prepared by two efficient methods and utilized as donor rings to assemble calix[4]arene [2]catenanes based on π-stacking interaction between hydroquinone and bipyridinium units. Treatment of calix[4]arene crown ethers 4, 10a, or 10b, whose cone conformation was fixed by intramolecular hydrogen bonding within the calix[4]arene moiety, with dicationic salt 15·2PF6 and dibromide 16 afforded the corresponding [2]catenanes 17a·4PF6, 17b·4PF6, and 17b·4PF6in 20%, 53%, and 55% yields, respectively, whereas from the reactions of 15·2PF6and dibromide 16 in the presence of conformationally flexible 11 or 12 with a cone conformation kept by two propyl groups, [2]catenanes 18-4PF6 and 19-4PF6 were obtained in 12% and 6% yields. [2]Catenanes 21a· 4Cl, 21b·4Cl, and 21c·4Cl, incorporating calix[4]arene in both the donor and acceptor rings, were also successfully assembled from 10a or 10b, 16, and dicationic salts 20a·2PF6 or 20b·2PF6. The dynamic 1H NMR and absorption spectra of the [2]catenanes have been investigated, which revealed a strongest donor-acceptor interaction in 17a·4PF6 and that the cone [2]catenanes 17a-c·4PF6 can isomerize to the partial cone isomer at high temperature. The difference of the dynamic properties of these catenanes was discussed. The results demonstrate that catenation is one new general method to change the conformational distributions of calix[4]arenes.

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.

Preparation of diaza dioxa dithia crown p-tert-butylcalix[4]arene by S-alkylation reactions: Use of metallo-calix[4]arene complexes as reaction templates

New nickel-thiolato-calix[4]arene complexes were produced by mean of metal-template synthesis employing S-alkylation of a nickel thiolato complex with a dichloroethyl-or a dibromoethylcalix[4]arene derivative. Demetallation of a nickel-thiolato-calix[4]arene complex resulted in a p-tert-butylcalix[4]arene derivative containing two N-, two O-and two S-donors.

Use of organoboranes in the synthesis of pheromones: A convenient synthesis of (Z)-6-heneicosen-11-one and (Z)-5-undecen-2-one, pheromones from the Douglas Fir Tussock Moth and the Bontebok, respectively

Treatment of thexylborane with a halomagnesiumdialkylcuprate afforded the corresponding (R-alkyl)thexylborane in favourable yields. A second reaction with a halomagnesiumdialkenylcuprate produced the totally mixed (R-alkyl)(E-alkenyl)thexylborane. Subsequent treatment with sodium cyanide and benzoyl chloride followed by alkaline peroxide yielded an unsaturated ketone. In this way, (Z)-6-heneicosen-11-one, a sex pheromone of the Douglas Fir Tussock Moth, and (Z)-5-undecen-2-one, a pheromone from the pedal gland of the Bontebok, were prepared.

Basket-shaped hosts with semi-flexible handles

Basket-shaped hosts were synthesized starting from the concave building block 4: .To this end, oligo(oxyethylene)bridges, containing different aromatic rings, were attached to the 3,6- and 3',6'-positions of the xylylene rings of 4.These bridges include 5,6-benzo-1,4,7,10-tetraoxadec-5-ene, 5,6,7-benzo-1,4,8,11-tetraoxaundeca-5,6-diene, 5,6-(2,3-naphtho)-1,4,7,10-tetraoxa-dec-5-ene, 8,9-benzo-1,4,7,10,13,16-hexaoxahexadec-8-ene and 8,9-(2,3-naphtho)-1,4,7,10,13,16-hexaoxahexadec-8-ene chains.Alkali-metal ions and protonated aliphatic or aromatic diamines are bound in these baskets in a 1:1 host/guest ratio.For the metal ions, a clamshell-like or a sandwich-like complex is proposed.Aliphatic diammonium guests are bound in such a way that the methylene chains are wedged in between the o-xylylene units of the host, as concluded from the upfield shifts observed in the 1H NMR spectra of the guest CH2 protons.Free energies of binding of the new hosts with nineteen guests were measured using the picrate extraction technique.The highest -ΔG0 values were obtained for the complexes with the diammonium salts (-ΔG0 values up to 13.4 kcal/mol).