1-mercapto-11-hydroxy-3,6,9-trioxaundecane

Base Information

• Chemical Name: 1-mercapto-11-hydroxy-3,6,9-trioxaundecane
• CAS No.: 90952-27-5
• Molecular Formula: C8H18O4S
• Molecular Weight: 210.295
• European Community (EC) Number: 804-584-5
• DSSTox Substance ID: DTXSID40440360
• Nikkaji Number: J1.118.279H
• Mol file: 90952-27-5.mol

Synonyms:11-mercapto-3,6,9-trioxyundecan-1-ol;tetraethylene glycol monothiol;12-mercapto-3,6,9,12-tetraoxadodecan-1-ol;11-mercapto-3,6,9-trioxaundecanol;Ethanol,2-[2-[2-(2-mercaptoethoxy)ethoxy]ethoxy];1-mercapto-11-hydroxy-3,6,9-trioxaundecane;mercaptotetraethylene glycol;

Chemical Property of 1-mercapto-11-hydroxy-3,6,9-trioxaundecane

Chemical Property:

• Refractive Index: n20/D1.481
• Flash Point: >110 °C
• PSA: 86.72000
• Density: 1.098 g/mL at 25 °C
• LogP: -0.04170
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 210.09258022
• Heavy Atom Count: 13
• Complexity: 92.2

Purity/Quality:

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

Thiol-PEG4-alcohol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,C
• Statements: 34-38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(COCCOCCOCCS)O
• Description: Thiol-PEG4-Alcohol is a crosslinker containing a hydroxyl group and a thiol group. The thiol group reacts with maleimide, OPSS, vinylsulfone and transition metal surfaces including gold, silver, etc. The hydrophilic PEG spacer increases solubility in aqueous media.
• Uses: Oligo-ehtylene glycol of peptides and small molecules (PEGylation)PEG-disulfide formationultra-thin protein-resistant monolayersDensely packed monolayer and a flexible-hydrophilic oligo ethylene glycol arm for avoiding non-specific adsorption

Technology Process of 1-mercapto-11-hydroxy-3,6,9-trioxaundecane

There total 7 articles about 1-mercapto-11-hydroxy-3,6,9-trioxaundecane 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: 99.0%

S-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)thioacetate (223611-42-5,165729-83-9) → 2-(2-(2-(2-mercaptoethoxy)ethoxy)ethoxy)ethan-1-ol (90952-27-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201601048

Reference yield: 83.3%

p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester (77544-60-6) → 2-(2-(2-(2-mercaptoethoxy)ethoxy)ethoxy)ethan-1-ol (90952-27-5)

Guidance literature:

p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester; With thiourea; In ethanol; for 24h; Reflux; Inert atmosphere;

With sodium hydroxide; In ethanol; water; for 3h; Reflux; Inert atmosphere;

DOI:10.1039/c1nj20206e

Reference yield: 52.0%

→ 2-(2-(2-(2-mercaptoethoxy)ethoxy)ethoxy)ethan-1-ol (90952-27-5)

Guidance literature:

With thiourea; In water; for 18h; Reflux;

With sodium hydroxide; In water; for 3h; Reflux;

upstream raw materials:

S-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)thioacetate

2-{2-[2-(2-bromoethoxy)ethoxy]ethoxy}ethan-1-ol

Tetraethylene glycol

p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester

Downstream raw materials:

2-(2-{2-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethylsulfanyl)-ethoxy]-ethoxy}-ethoxy)-ethanol

C₂₅H₃₆O₉S₂

C₆₈H₁₃₇N₁₅O₇S

C₆₈H₁₀₅N₁₅O₇S

Refernces

• 1、 -. "Smooth receptor ligand". Paragraph 0085; 0252; 0255; 0264. . Retrieved 2020/04/01.
• 2、 Tegeder, Patricia,Freitag, Matthias,Chepiga, Kathryn M.,Muratsugu, Satoshi,M?ller, Nadja,Lamping, Sebastian,Tada, Mizuki,Glorius, Frank,Ravoo, Bart Jan. "N-Heterocyclic Carbene-Modified Au–Pd Alloy Nanoparticles and Their Application as Biomimetic and Heterogeneous Catalysts". supporting information. p. 18682 - 18688. Retrieved 2018/11/23.