PENTA(ETHYLENE GLYCOL) DI-P-TOLUENESULFONATE

Base Information

• Chemical Name: PENTA(ETHYLENE GLYCOL) DI-P-TOLUENESULFONATE
• CAS No.: 41024-91-3
• Molecular Formula: C24H34 O10 S2
• Molecular Weight: 546.66
• Hs Code.: 2909499000
• Mol file: 41024-91-3.mol

Synonyms:3,6,9,12-Tetraoxatetradecane-1,14-diol,bis(4-methylbenzenesulfonate) (9CI); 1,14-Bis(tosyloxy)-3,6,9,12-tetraoxatetradecane;Bis(p-toluenesulfonyl)pentaethylene glycol; NSC 625453; Pentaethylene glycolbis(4-toluenesulfonate); Pentaethylene glycol bis(p-toluenesulfonate);Pentaethylene glycol di-p-toluenesulfonate; Pentaethylene glycol di-p-tosylate;Pentaethylene glycol ditosylate

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

Chemical Property:

• Vapor Pressure: 1.26E-16mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Boiling Point: 661.4°Cat760mmHg
• Flash Point: 353.8°C
• PSA: 140.42000
• Density: 1.251g/cm³
• LogP: 4.64220
• Sensitive.: Hygroscopic
• Water Solubility.: Not miscible or difficult to mix in water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,6,9,12-Tetraoxatetradecane-1,14-diylbis(4-Methylbenzenesulfonate) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Tos-PEG6-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: PENTA(ETHYLENE GLYCOL) DI-P-TOLUENESULFONATE is used to prepare calix[4]arenes,1 calix[5]arenes,2 and crown ethers.3 Pentaethylene glycol di-p-toluenesulfonate is used in the preparation of calix[4]arenes, calix[5]arenes, and crown ethers. It is also used in the preparation of 3?-formylbenzo-18-crown-6 by undergoing coupling reaction with 2,3-dihydroxybenzaldehyde.

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

There total 4 articles about PENTA(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%

Pentaethylene glycol (4792-15-8) + p-toluenesulfonyl chloride (98-59-9) → penta(ethylene glycol) bis(p-toluenesulfonate) (41024-91-3)

Guidance literature:

With potassium hydroxide; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/j.bmc.2007.04.065

Reference yield: 78.0%

Pentaethylene glycol (4792-15-8) + p-toluenesulfonyl chloride (98-59-9) → penta(ethylene glycol) bis(p-toluenesulfonate) (41024-91-3) + 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate (155130-15-7)

Guidance literature:

With potassium iodide; silver(l) oxide; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/ol020071y

Reference yield:

1,2-bis(2-chloroethoxy)ethane (112-26-5,27252-69-3) → penta(ethylene glycol) bis(p-toluenesulfonate) (41024-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / 36 h / Inert atmosphere; Reflux

2: sodium hydroxide / water; tetrahydrofuran / 3 h / Inert atmosphere

With potassium hydroxide; sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2014.10.050

upstream raw materials:

ethylene glycol

1,2-bis(2-chloroethoxy)ethane

p-toluenesulfonyl chloride

Pentaethylene glycol

Downstream raw materials:

4'-acetylbenzo-18-crown-6

5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-dihydroxycalix[4]arene-crown-6

6,7,9,10,12,13,15,16,18,19-decahydro-2,4,21,23-tetramethyldibenzo<1,4,7,10,13,16>hexaoxacycloeicosin

19,21-bis(ethoxycarbonyl)-2,5,8,11,14,17-hexaoxa-20-thiabicyclo<16.3.0>heneicosa-1(21),18-diene

Refernces

• 1、 El Khoury, Anton,Seidler, Paul M.,Eisenberg, David S.,Harran, Patrick G.. "Catalytic Synthesis of PEGylated EGCG Conjugates that Disaggregate Alzheimer's Tau". . p. 4263 - 4271. Retrieved 2021/06/18.
• 2、 Kim, Nam-Kyun,Sogawa, Hiromitsu,Takata, Toshikazu. "Cu-tethered macrocycle catalysts: Synthesis and size-selective CO2-fixation to propargylamines under ambient conditions". supporting information. . Retrieved 2020/05/01.