Bis-Propargyl-PEG9

Base Information

• Chemical Name: Bis-Propargyl-PEG9
• CAS No.: 1092554-87-4
• Molecular Formula: C₂₂H₃₈O₉
• Molecular Weight: 446.538
• Mol file: 1092554-87-4.mol

Synonyms:4,7,10,13,16,19,22,25,28-nonaoxahentriaconta-1,30-diyne

Chemical Property of Bis-Propargyl-PEG9

Chemical Property:

• Boiling Point: 495.5±40.0 °C(Predicted)
• Density: 1.072±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Bis-propargyl-peg9 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Bis-propargyl-PEG9 is crosslinking reagent containing two propargyl groups. These functional groups enable the formation of triazole linkages with azide-bearing compounds with the presence of copper catalyst. The hydrophilicity of the molecule is improved because of the PEG chain.
• Uses: Bis-propargyl-peg9 is used as a bivalent estrogen receptor ligand.

Technology Process of Bis-Propargyl-PEG9

There total 3 articles about Bis-Propargyl-PEG9 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: 85.0%

octaethylene glycol (5117-19-1) + propargyl bromide (106-96-7) → 4,7,10,13,16,19,22,25,28-nonaoxahentriaconta-1,30-diyne (1092554-87-4)

Guidance literature:

octaethylene glycol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; Inert atmosphere;

propargyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.carres.2012.02.034

Reference yield: 52.0%

toluene-4-sulfonic acid 2-{2-[2-(2-ethynyloxyethoxy)-ethoxy]-ethoxy}-ethyl ester (875770-32-4) + 3,6,9,12-tetraoxapentadec-14-yn-1-ol (87450-10-0) → 4,7,10,13,16,19,22,25,28-nonaoxahentriaconta-1,30-diyne (1092554-87-4)

Guidance literature:

3,6,9,12-tetraoxapentadec-14-yn-1-ol; With sodium hydride; In tetrahydrofuran; mineral oil; for 1h;

toluene-4-sulfonic acid 2-{2-[2-(2-ethynyloxyethoxy)-ethoxy]-ethoxy}-ethyl ester; In tetrahydrofuran; mineral oil; at 20 ℃; for 24h;

DOI:10.5012/bkcs.2011.32.11.3933

Reference yield:

Tetraethylene glycol (112-60-7) → 4,7,10,13,16,19,22,25,28-nonaoxahentriaconta-1,30-diyne (1092554-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h

1.2: 20 h / 20 °C / Cooling with ice

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h

2.2: 24 h / 20 °C

With sodium hydride; In tetrahydrofuran; mineral oil;

DOI:10.5012/bkcs.2011.32.11.3933

upstream raw materials:

toluene-4-sulfonic acid 2-{2-[2-(2-ethynyloxyethoxy)-ethoxy]-ethoxy}-ethyl ester

3,6,9,12-tetraoxapentadec-14-yn-1-ol

Tetraethylene glycol

octaethylene glycol

Downstream raw materials:

C₇₂H₉₂N₆O₂₁

C₄₀H₆₀N₆O₁₃

Refernces

• 1、 Jervis, Peter J.,Moulis, Marie,Jukes, John-Paul,Ghadbane, Hemza,Cox, Liam R.,Cerundolo, Vincenzo,Besra, Gurdyal S.. "Towards multivalent CD1d ligands: Synthesis and biological activity of homodimeric α-galactosyl ceramide analogues". . p. 152 - 162. Retrieved 2012.