TRI(ETHYLENE GLYCOL) DI-P-TOLUENESULFONATE

Base Information

• Chemical Name: TRI(ETHYLENE GLYCOL) DI-P-TOLUENESULFONATE
• CAS No.: 19249-03-7
• Molecular Formula: C20H26O8S2
• Molecular Weight: 458.554
• Hs Code.: 29093090
• European Community (EC) Number: 628-844-0
• NSC Number: 244980
• UNII: PHX64WPG5J
• DSSTox Substance ID: DTXSID40940911
• Nikkaji Number: J211.394E
• Wikidata: Q72510629
• ChEMBL ID: CHEMBL2179200
• Mol file: 19249-03-7.mol

Synonyms:Ethanol,2,2'-[1,2-ethanediylbis(oxy)]bis-, bis(4-methylbenzenesulfonate) (9CI);Triethylene glycol, di-p-toluenesulfonate (6CI,7CI,8CI);1,2-Ethanediylbis(oxy-2,1-ethanediyl) bis(4-methylbenzenesulfonate);1,8-Bis(p-tolylsulfonyloxy)-3,6-dioxaoctane;1,8-Bis(tosyloxy)-3,6-dioxaoctane;2-[2-[2-[[(4-Methylphenyl)sulfonyl]oxy]ethoxy]ethoxy]ethyl4-methylbenzenesulfonate;3,6-Dioxaoctane-1,8-diol ditosylate;NSC 244980;Triethylene glycol bis(4-toluenesulfonate);Triethylene glycolbis(p-toluenesulfonate);Triethylene glycol bis(p-tosylate);Triethylene glycoldi-4-toluenesulfonate;Triethylene glycol di-p-tosylate;Triethylene glycolditoluenesulfonate;Triethylene glycol ditosylate;Triethyleneglycolbis(toluenesulfonate);

Chemical Property of TRI(ETHYLENE GLYCOL) DI-P-TOLUENESULFONATE

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 4.27E-14mmHg at 25°C
• Melting Point: 78-82 °C(lit.)
• Refractive Index: 1.544
• Boiling Point: 608.4 °C at 760 mmHg
• Flash Point: 321.7 °C
• PSA: 121.96000
• Density: 1.281 g/cm³
• LogP: 4.60900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in ethanol.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 458.10691013
• Heavy Atom Count: 30
• Complexity: 605

Purity/Quality:

98% ^*data from raw suppliers

(Ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl)bis(4-Methylbenzenesulfonate) ^*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:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOS(=O)(=O)C2=CC=C(C=C2)C
• Description: Tos-PEG4-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: Tri(ethylene glycol) di-p-toluenesulfonate is used in the synthesis of 1-[4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-phenyl] ethanone.

Technology Process of TRI(ETHYLENE GLYCOL) DI-P-TOLUENESULFONATE

There total 5 articles about TRI(ETHYLENE GLYCOL) DI-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) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethylene glycol di-(p-toluenesulfonate) (19249-03-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 24h;

DOI:10.1039/b600848h

Reference yield: 92.0%

p-toluenesulfonyl chloride (98-59-9) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 8-tosyloxy-3,6-dioxaoctanol (77544-68-4) + triethylene glycol di-(p-toluenesulfonate) (19249-03-7)

Guidance literature:

With potassium iodide; silver(l) oxide; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1021/ol020071y

Reference yield: 91.0%

toluene-4-sulfonic acid (104-15-4) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethylene glycol di-(p-toluenesulfonate) (19249-03-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 20h;

DOI:10.1002/anie.201406764

upstream raw materials:

p-toluenesulfonyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

toluene-4-sulfonic acid

Downstream raw materials:

6,7,9,10,12,13,22,23,24,25-decahydro-5,8,11,14,19,28-hexaoxa-22,25-diaza-dibenzo[a,m]cyclotetracosene-21,26-dione

7,8,9,10-tetraphenyl-1,4-dioxa-7,10-diaza-cyclododec-8-ene

7,16-bis(ethoxycarbonyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane

N,N'-ditosyl-1,4-dioxa-7,10-diazacyclododecane

Refernces

Highly fluorinated cyclodextrins and their host-guest interactions

10.1039/c0cc00616e

The research focuses on the synthesis and characterization of highly fluorinated, water-soluble cyclodextrins and their interactions with both fluorinated and non-fluorinated guest molecules. The cyclodextrins were synthesized through a three-step process: perchlorination at C6 using methylsulfonylchloride, functionalization with trifluoroethylthiol in the presence of NaH, and finally, reaction with triethyleneglycol p-toluenesulfonate ester in the presence of NaH. The synthesized cyclodextrins were analyzed using isothermal titration calorimetry (ITC) and NMR spectroscopy to determine their binding constants, thermodynamic parameters, and stoichiometry with various guest molecules. The results indicated that the fluorinated cyclodextrins preferentially interacted with fluorinated guests, demonstrating the significant role of the fluorophobic effect in stabilizing host-guest complexes in water.