6315-52-2

Basic information

• Product Name: 1,2-BIS(TOSYLOXY)ETHANE
• Synonyms: AIDS124301;1,2-ETHANEDIOLBIS(4-METHYLBENZENESULFONATE);1,2-Bis(4-methylbenzenesulfonyloxy)ethane;1,2-Bis(p-tolylsulfonyloxy)ethane;1,2-Di(tosyloxy)ethane;1,2-Ethanediol 1,2-bis(4-methylbenzenesulfonate):1,2-Ethanediol:1,2-bis(4-methylbenzenesulfonate);1,2-Ethanediol ditosylate;1,2-Ethylene ditosylate
• CAS NO: 6315-52-2
• Molecular Formula: C₁₆H₁₈O₆S₂
• Molecular Weight: 370.44
• Mol File: 6315-52-2.mol
• Article Data: 61

Chemical Properties

• Melting Point: 124-127 °C(lit.)
• Boiling Point: 544.3 °C at 760 mmHg
• Flash Point: 283 °C
• Appearance: /
• Density: 1.326
• Vapor Pressure: 2.35E-11mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• Water Solubility: Slightly soluble in water.
• BRN: 2399520
• CAS DataBase Reference: 1,2-BIS(TOSYLOXY)ETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BIS(TOSYLOXY)ETHANE(6315-52-2)
• EPA Substance Registry System: 1,2-BIS(TOSYLOXY)ETHANE(6315-52-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 6315-52-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless solid

Uses

Ethylene di(p-toluenesulfonate) [Ethylene glycol ditosylate] has been used in the synthesis of, cyclohexyl-fused 1,4,7-triazacyclononane, 1,2-ethylenecalix[6]arene, 1,3- and 1,4-calix[6]crown-3, 1,3- and 1,4-calix[6]crown-4, 1,4-calix[6]benzocrown-4, 1,2- and 1,3-calix[6]crown-5.

InChI:InChI=1/C16H18O6S2/c1-13-3-7-15(8-4-13)23(17,18)21-11-12-22-24(19,20)16-9-5-14(2)6-10-16/h3-10H,11-12H2,1-2H3

Upstream product

• 107-21-1 ethylene glycol 
• 98-59-9 p-toluenesulfonyl chloride 
• 74-85-1 ethene 
• 108164-35-8 C₁₀H₈F₇IO₄S 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 4124-41-8 p-toluenesulfonylanhydride 
• 75-21-8 oxirane 
• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 106-93-4 ethylene dibromide 

Downstream Products

• 64873-75-2 2,2'-dimethyl-3,3'-ethane-1,2-diyl-bis-benzothiazolium; bis-(toluene-4-sulfonate) 
• 607-26-1 N,N'-ethylenediphthalimide 
• 5460-83-3 2-(1,3-dioxoisoindolin-2-yl)ethyl 4-methylbenzenesulfonate 
• 2615-15-8 pentaethylene glycol 
• 85356-12-3 2,5-Dimorpholino-2,5-diphenyladiponitrile 
• 113487-25-5 ethylene glycol di-tertbutylphenoxide 
• 259541-67-8 2,6-dimethoxyphenylphosphirane 
• 268746-64-1 25,27-bis(2-p-toluenesulfonyloxyethyloxy)-26,28-bis(1-propyloxy)calix[4]arene, 1,3-alternate 
• 14174-08-4 benzo-12-crown-4 
• 850834-26-3 2-(2,5-difluorophenoxy)ethyl toluene-4-sulphonate 
• 95388-12-8 1,3-bis[N,N'-bis(p-toluenesulfonyl)-1,4,7-triaza-1-cyclononyl]ethane 
• 1096545-35-5 2,6-diethyl-1,4,7-tris(p-toluenesulfonyl)triazacyclononane 
• 1016167-67-1 2-[4-(4-(2-tosylethoxy)phenyl)piperazin-1-ylmethyl]pyrazolo[1,5-a]pyridine 
• 1016167-50-2 4-[4-(2-tosylethoxy)phenyl]piperazine-1-carboxylic acid t-butyl ester 

Relevant articles and documents

Hydrophilic Quaternary Ammonium Ionenes—Is There an Influence of Backbone Flexibility and Topology on Antibacterial Properties?

The antimicrobial properties of polycations are strongly affected by the structural features such as the backbone flexibility and topology (isomerism) through the polymer ability to attain proper conformation in interaction with the cell membrane. In this paper, a synthesis and biocidal properties evaluation of ionenes characterized by different backbone topology (isomerism) and flexibility are presented. The findings reveal influence of variation in topology on activity against different microorganisms, and general positive effect of improved flexibility. Furthermore, one of the obtained ionenes displays degradable properties in near physiological environment (phosphate-buffered saline pH 7.4, 37 °C). The degradation proceeds via Hofmann elimination reaction and the products are not of acidic character. For the first time a new class of degradable ionenes with a high antimicrobial potential is presented.

Synthesis and characterization of novel triarylmethane-based dyes for thermally stable blue color filters

Two new triarylmethane-based dye molecules with a dimeric structure, TAM-1 and TAM-2, were designed and synthesized as potential blue color filter materials for liquid-crystal displays. The dimeric structure of TAM-1 was designed to improve the thermal stability of a well-known blue dye, Victoria Blue BO. TAM-2 was designed to further improve the solubility of TAM-1 by introducing long alkyl ester groups. The synthesized dyes TAM-1 and TAM-2 were transmissive in the wavelength range of 410-460 nm and showed good thermal stability with 5% weight degradation temperatures (T5d) of 259 °C and 289 °C, respectively, and less than 1% of weight loss at 230 °C. Moreover, TAM-2 showed excellent solubility (20.1 wt%) as opposed to Victoria Blue BO (0.03 wt%) and TAM-1 (3.5 wt%) in PGMEA.

Revisiting complexation between DNA and polyethylenimine: Does the disulfide linkage play a critical role in promoting gene delivery?

Despite its cytotoxicity, polyethylenimine (PEI) is still used as a golden reference in gene transfection. Long PEI chains are more effective but also more cytotoxic. To solve this problem, an alternative strategy is to link short PEI chains into a longer PEI with disulfide bonds because they are degradable in the cell. However, how PEI promotes gene transfection is still unclear. Also, the chain length of PEI is also increased as disulfide bonds are formed. Therefore, it is important to investigate whether the increase in transfection efficiency is attributable to the disulfide linkage, chain size, or both. To distinguish between such factors, a novel method is developed here tomake longer linear PEI with disulfide bonds (lPEIs-s) by linking the mercapto groups of short linear PEI (lPEIi). By comparing the physiochemical properties and the transfection efficiencies of short lPEIi, long lPEIs-s, and un-degradable long PEI, it is found that introducing disulfide bonds instead of directly using longer PEI chains has less effect on gene transfection, and it is the chain length that plays a key role in promoting gene transfection.

Synthesis and biological evaluation of PET tracers designed for imaging of calcium activated potassium channel 3.1 (KCa3.1) channels: In vivo

Expression of the Ca2+ activated potassium channel 3.1 (KCa3.1) channel (also known as the Gàrdos channel) is dysregulated in many tumor entities and has predictive power with respect to patient survival. Therefore, a positron emission tomography (PET) tracer targeting this ion channel could serve as a potential diagnostic tool by imaging the KCa3.1 channel in vivo. It was envisaged to synthesize [18F]senicapoc ([18F]1) since senicapoc (1) shows high affinity and excellent selectivity towards the KCa3.1 channels. Because problems occurred during 18F-fluorination, the [18F]fluoroethoxy senicapoc derivative [18F]28 was synthesized to generate an alternative PET tracer targeting the KCa3.1 channel. Inhibition of the KCa3.1 channel by 28 was confirmed by patch clamp experiments. In vitro stability in mouse and human serum was shown for 28. Furthermore, biodistribution experiments in wild type mice were performed. Since [18F]fluoride was detected in vivo after application of [18F]28, an in vitro metabolism study was conducted. A potential degradation route of fluoroethoxy derivatives in vivo was found which in general should be taken into account when designing new PET tracers for different targets with a [18F]fluoroethoxy moiety as well as when using the popular prosthetic group [18F]fluoroethyl tosylate for the alkylation of phenols.

Second-Sphere Interaction Promoted Turn-On Fluorescence for Selective Sensing of Organic Amines in a TbIII-based Macrocyclic Framework

Guided by a second-sphere interaction strategy, we fabricated a Tb(III)-based metal—organic framework (MMCF-4) for turn-on sensing of methyl amine with ultra-low detection limit and high turn-on efficiency. MMCF-4 features lanthanide nodes shielded in a nonacoordinate geometry along with secondary coordination spheres that are densely populated with H-bond interacting sites. Nonradiative routes were inhibited by binding-induced rigidification of the ligand on the second coordination sphere, resulting in luminescence amplification. Such remote interacting mechanism involved in the turn-on sensing event was confirmed by single-crystal X-ray diffraction and molecular dynamic simulation studies. The design of both primary and secondary coordination spheres of Tb(III) enabled the first turn-on sensing of organic amines in aqueous conditions. Our work suggests a promising strategy for high-performance turn-on sensing for Ln-MOFs and luminous materials driven by other metal chromophores.