Diethylene Glycol Bis(p-toluenesulfonate)

Base Information

• Chemical Name: Diethylene Glycol Bis(p-toluenesulfonate)
• CAS No.: 7460-82-4
• Molecular Formula: C18H22O7S2
• Molecular Weight: 414.5
• Hs Code.: 2904100000
• European Community (EC) Number: 628-596-3
• NSC Number: 404215
• UNII: H92EG77LWH
• DSSTox Substance ID: DTXSID80996114
• Nikkaji Number: J211.393G
• Wikidata: Q72461890
• Mol file: 7460-82-4.mol

Synonyms:7460-82-4;Diethylene Glycol Bis(p-toluenesulfonate);Diethylene glycol ditosylate;Oxybis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate);Diethylene glycol di(p-toluenesulfonate);Tos-PEG3-Tos;2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethyl 4-methylbenzenesulfonate;di(2-tosyloxyethyl)ether;Bis(2-tosyloxyethyl)ether;H92EG77LWH;Ethanol, 2,2'-oxybis-, bis(4-methylbenzenesulfonate);MFCD00026001;NSC-404215;2-{2-[(4-methylbenzenesulfonyl)oxy]ethoxy}ethyl 4-methylbenzene-1-sulfonate;2,2'-Oxydiethyl ditosylate;Bis-Tos-PEG2;2-(2-(4-METHYLPHENYL)SULFONYLOXYETHOXY)ETHYL 4-METHYLBENZENESULFONATE;C18H22O7S2;NSC404215;diethyleneglycol ditosylate;CBMicro_047760;UNII-H92EG77LWH;Bis(2-tosyloxyethyl) Ether;diethyleneglycol-di-p-tosylate;oxydiethane-2,1-diyl bis(4-methylbenzenesulfonate);SCHEMBL922407;Oxybis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate);AMY4495;DTXSID80996114;Tos-PEG-Tos, MW 1,000;Tos-PEG-Tos, MW 2,000;Tos-PEG-Tos, MW 3,000;Tos-PEG-Tos, MW 5,000;Tos-PEG-Tos, MW 8,000;DI(2-TOSYLOXYETHYL) ETHER;Tos-PEG-Tos, MW 10,000;STK387255;2,2'-OXYBIS(ETHYL TOSYLATE);AKOS003617847;CS-W011664;DIETHYLENE GLYCOL DI-P-TOSYLATE;DS-2748;HY-W010948;NSC 404215;DIETHYLENE GLYCOL BIS(P-TOSYLATE);3-OXAPENTANE-1,5-DIOL DITOSYLATE;Bis[2-(p-toluenesulfonyloxy)ethyl] Ether;BP-20713;BP-26100;BP-26101;BP-26102;BP-26103;BP-26104;BP-26105;SY052010;BIM-0047971.P001;D2457;FT-0624888;DIETHYLENE GLYCOL DI-P-TOLUENESULFONATE;2,2-Oxybisethane bis(4-methylbenzenesulfonate);3-oxapentane-1,5-diyl bis(p-toluenesulfonate);Diethylene glycol di(p-toluenesulfonate), 98%;E10130;DIETHYLENE GLYCOL BIS(4-TOLUENESULFONATE);1,5-BIS(P-TOLYLSULFONYLOXY)-3-OXAPENTANE;A838176;SR-01000199114;J-520315;SR-01000199114-1;3-OXA-1,5-PENTANEDIYL BIS(P-TOLUENESULFONATE);BIS(.BETA.-(4-TOLUENESULFONYLOXY)ETHYL) ETHER;Oxydi(ethane-2,1-diyl) bis(4-methylbenzene-1-sulfonate);2,2'-oxybis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate);ETHANOL, 2,2'-OXYBIS-, 1,1'-BIS(4-METHYLBENZENESULFONATE);2-(2-(4-METHYLPHENYL)SULFONYLOXYETHOXY)ETHYL 4-METHYLPHENYLSULFONATE;methyl?4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;4-methylbenzenesulfonic acid 2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethyl ester

Chemical Property of Diethylene Glycol Bis(p-toluenesulfonate)

Chemical Property:

• Appearance/Colour: colorless to white powder or crystals
• Vapor Pressure: 6.78E-13mmHg at 25°C
• Melting Point: 87-89 °C(lit.)
• Refractive Index: 1.554
• Boiling Point: 581.2 °C at 760 mmHg
• Flash Point: 305.3 °C
• PSA: 112.73000
• Density: 1.301 g/cm³
• LogP: 4.59240
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 414.08069538
• Heavy Atom Count: 27
• Complexity: 562

Purity/Quality:

98% ^*data from raw suppliers

Diethylene glycol di(p-toluenesulfonate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOS(=O)(=O)C2=CC=C(C=C2)C
• Description: Tos-PEG3-Tos is a PEG linker containing two tosyl groups. The hydrophilic PEG spacer increases solubility in aqueous media. The tosyl group is a very good leaving group for nucleophilic substitution reactions.
• Uses: Diethylene glycol di(p-toluenesulfonate) was used in the synthesis of bis(dibenzosulfoxo)-27,30,35,38-tetramethyl-24-crown-6, bis(dibenzosulfoxo)-21,24,29,32-tetramethyl-18-crown-4, dibenzosulfoxo-15,18-dimethyl-12-crown-3 and dibenzosulfoxo-12,15-dimethyl-9-crown-2 macrocycles.

Technology Process of Diethylene Glycol Bis(p-toluenesulfonate)

There total 4 articles about Diethylene Glycol Bis(p-toluenesulfonate) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

p-toluenesulfonyl chloride (98-59-9) + diethylene glycol (111-46-6) → diethylene glycol ditosylate (7460-82-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 24h;

DOI:10.1039/b600848h

Reference yield: 92.0%

p-toluenesulfonyl chloride (98-59-9) + diethylene glycol (111-46-6) → 5-tosyloxy-3-oxapentanol (118591-58-5) + diethylene glycol ditosylate (7460-82-4)

Guidance literature:

With potassium iodide; silver(l) oxide; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1021/ol020071y

Reference yield: 8.0%

→ diethylene glycol ditosylate (7460-82-4)

Guidance literature:

upstream raw materials:

p-toluenesulfonyl chloride

diethylene glycol

hypochlorous acid 4-methylbenzene sulfonic anhydride

Downstream raw materials:

(Z)-7,8,9-triphenyl-2,3,6,7-tetrahydro-5H-[1,4,7]dioxazonine

(Z)-4,5,6,7-tetraphenyl-2,3,4,7,8,9-hexahydro-[1,4,7]oxadiazonine

8,16,22-tris-(toluene-4-sulfonyl)-7,8,9,10,17,18,21,22-octahydro-6H,16H,20H-5,11,19-trioxa-8,16,22-triaza-dibenzo[a,j]cyclooctadecene

4,10-bis(p-tolylsulphonyl)-1,7-dioxa-4,10-diazacyclododecane

Refernces

¹⁸F-Labelled vorozole analogues as PET tracer for aromatase

10.1002/jlcr.1502

The research aims to develop 18F-labeled vorozole analogues as PET tracers for detecting the enzyme aromatase, which converts androgens to estrogens and may influence mood and mental status. The study involves one- and two-step syntheses of two 18F-labeled vorozole analogues, [18F]FVOZ and [18F]FVOO, using key chemicals such as ethane-1,2-diyl bis(4-methylbenzenesulfonate), oxydiethane-2,1-diyl bis(4-methylbenzenesulfonate), and 1-bromo-2-fluoroethane. The one-step synthesis achieved higher radiochemical yields (36–99%) and specific radioactivities (100 GBq/mmol for [18F]FVOZ and 80 GBq/mmol for [18F]FVOO) compared to the two-step synthesis. In vitro autoradiography using frozen rat brains showed specific binding in regions corresponding to previous [11C]VOZ studies. Metabolite studies revealed that [18F]FVOZ was more stable in plasma than [18F]FVOO. The one-step synthesis method is highlighted as a more reproducible and potentially automatable approach for future tracer development.

New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-, Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands

10.1021/jo00046a020

The study focuses on the synthesis and characterization of eleven new chiral macrocycles (1-11) of the pyridino-18-crown-6 type. These compounds were prepared using various starting materials such as (S)-(+)-2-phenylglycine, formic acid, acetic anhydride, and diethylene glycol ditosylate, among others. The roles of these chemicals are crucial in the formation of the chiral diamines and glycols, which are then used to create the macrocyclic structures through cyclization reactions with compounds like dimethyl 2,6-pyridinedicarboxylate and O,O'-dimethyl 2,6-pyridinedicarbothioate. The study also investigates the enantiomeric recognition properties of these new chiral ligands with (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate using 'H NMR spectral techniques. The interactions and the degree of enantiomeric recognition are analyzed based on the differences in free energy of activation values (ΔG*) and log K values. Additionally, the X-ray analyses of the dithionoamido ligands (2, 6, and 8) reveal significant deviations of the S and N atoms from the plane of the pyridine ring, indicating structural distortions. The study provides insights into the factors influencing enantiomeric recognition and the potential applications of these chiral macrocycles in enantiomeric separations.