13-Bromo-2,5,8,11-tetraoxatridecane

Base Information

• Chemical Name: 13-Bromo-2,5,8,11-tetraoxatridecane
• CAS No.: 110429-45-3
• Molecular Formula: C9H19BrO4
• Molecular Weight: 271.151
• European Community (EC) Number: 895-292-7
• DSSTox Substance ID: DTXSID10598605
• Wikidata: Q82494379
• Mol file: 110429-45-3.mol

Synonyms:110429-45-3;13-bromo-2,5,8,11-tetraoxatridecane;m-PEG4-bromide;Triethylene Glycol 2-Bromoethyl Methyl Ether;mPEG4-Br;m-PEG4-Br;2,5,8,11-Tetraoxatridecane, 13-bromo-;Bromo-PEG4-methoxy;Methyl-PEG4-bromide;1-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]-2-methoxyethane;MFCD12545963;2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethyl Bromide;ACMC-20mddm;1-Bromo-3,6,9,12-tetraoxatridecane;SCHEMBL2714525;DTXSID10598605;AKOS028109933;AS-66178;BP-21072;SY054556;DB-234106;HY-130161;CS-0105298;T2634;C70091;EN300-7412494

Chemical Property of 13-Bromo-2,5,8,11-tetraoxatridecane

Chemical Property:

• Vapor Pressure: 0.00256mmHg at 25°C
• Refractive Index: 1.4620 to 1.4660
• Boiling Point: 296.3oC at 760 mmHg
• Flash Point: 118.8oC
• PSA: 36.92000
• Density: 1.256g/cm3
• LogP: 1.07750
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 270.04667
• Heavy Atom Count: 14
• Complexity: 103

Purity/Quality:

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

Triethylene Glycol 2-Bromoethyl Methyl Ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCOCCOCCOCCBr
• Description: m-PEG4-bromide is a PEG linker containing a bromide group. The bromide (Br) is a very good leaving group for nucleophilic substitution reactions. The hydrophilic PEG spacer increases solubility in aqueous media.

Technology Process of 13-Bromo-2,5,8,11-tetraoxatridecane

There total 4 articles about 13-Bromo-2,5,8,11-tetraoxatridecane 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: 90.0%

tetraethylene glycol monomethyl ether (23783-42-8,95507-80-5) → 1-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-2-methoxy-ethane (110429-45-3,92450-98-1)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1039/c1ob05244f

Reference yield: 79.0%

2-(2-(2-(2-hydroxyethoxy)ethoxy)ethyl) methanesulfonate (130955-37-2) → 1-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-2-methoxy-ethane (110429-45-3,92450-98-1)

Guidance literature:

With tetrabutylammomium bromide; In acetonitrile; at 55 ℃; for 15h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield:

2-methoxy-ethanol (109-86-4,95507-80-5) + 1,2-bis-(2-bromo-ethoxy)-ethane (31255-10-4) → pentaglyme (1191-87-3) + 1-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-2-methoxy-ethane (110429-45-3,92450-98-1)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Title compound not separated from byproducts; 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 12 h;

DOI:10.1021/ja00071a021

upstream raw materials:

2-methoxy-ethanol

1,2-bis-(2-bromo-ethoxy)-ethane

tetraethylene glycol monomethyl ether

Tetraethylene glycol

Downstream raw materials:

benzyl 17-methyl-2,5,8,11-tetraoxa-14-thiaoctadecan-17-ylcarbamate

2-(4-(2,5,8,11-tetraoxatridecan-13-yloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-phenyl]-methanol

13,13'-(3,6-diiodo-1,2-phenylene)bis(oxy)bis(2,5,8,11-tetraoxatridecane)