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:

1,5-bis(2-acetylphenoxy)-3-oxapentane

stilbeno-9-crown-3

2,3,11,12-Tetraphenyl-2,3,11,12-didehydro<18>krone-6

1,5-bis(benzaldehydeoxy)-3-oxopentane

Refernces

• 1、 Xu, Zhi,Zhao, Shi-Jia,Deng, Jia-Lun,Wang, Qin,Lv, Zao-Sheng. "Design, Synthesis, and Antimycobacterial Activities of Diethylene Glycol Tethered Moxifloxacin–Isatin Hybrids". . p. 325 - 330. Retrieved 2019.
• 2、 Xu, Zhi,Zhao, Shi-Jia,Deng, Jia-Lun,Wang, Qin,Lv, Zao-Sheng. "Ciprofloxacin–Isatin Hybrids and Their Antimycobacterial Activities". . p. 319 - 324. Retrieved 2019.
• 3、 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.
• 4、 Huang, Boxuan,Li, Weijia,Mu, Yu,Shao, Liang,Su, Yangqing,Sun, Mengsi,Xu, Huan,Yang, Fan,Yu, Fei,Zhang, Jihong,Zhang, Yuan. "Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry". . p. 1759 - 1765. Retrieved 2021/11/18.