Bromo-PEG5-Azide

Base Information

• Chemical Name: Bromo-PEG5-Azide
• CAS No.: 1402411-90-8
• Molecular Formula: C₁₂H₂₄BrN₃O₅
• Molecular Weight: 370.244
• Mol file: 1402411-90-8.mol

Synonyms:

Chemical Property of Bromo-PEG5-Azide

Chemical Property:

Purity/Quality:

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

Bromo-PEG5-azide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Bromo-PEG5-azide contain a bromide group and a terminal azide. The bromide (Br) is a very good leaving group for nucleophilic reactions. The azide group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. PEG5 spacer increases solubility in aqueous media.

Technology Process of Bromo-PEG5-Azide

There total 4 articles about Bromo-PEG5-Azide 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: 92.0%

17-azido-3,6,9,12,15-pentaoxaheptadecan-1-ol (86770-69-6) → 17-azido-1-bromo-3,6,9,12,15-pentaoxaheptadecane (1402411-90-8)

Guidance literature:

17-azido-3,6,9,12,15-pentaoxaheptadecan-1-ol; With triethylamine; Methanesulfonic anhydride; In tetrahydrofuran; at 0 ℃; for 2h;

With lithium bromide; In tetrahydrofuran; for 5h; Reflux;

Reference yield: 79.0%

2[-2-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl p-tosylate (906007-10-1) → 17-azido-1-bromo-3,6,9,12,15-pentaoxaheptadecane (1402411-90-8)

Guidance literature:

With lithium bromide; In acetone; at 50 ℃; for 20h;

DOI:10.1002/anie.201202118

Reference yield:

pentaethylene glycol (2615-15-8) → 17-azido-1-bromo-3,6,9,12,15-pentaoxaheptadecane (1402411-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / tetrahydrofuran; water / 3.3 h / 0 °C

1.2: 14 h / 60 °C

2.1: sodium hydroxide / tetrahydrofuran; water / 4.5 h / 0 °C

3.1: lithium bromide / acetone / 20 h / 50 °C

With lithium bromide; sodium hydroxide; In tetrahydrofuran; water; acetone;

DOI:10.1002/anie.201202118

upstream raw materials:

2[-2-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl p-tosylate

pentaethylene glycol

17-azido-3,6,9,12,15-pentaoxaheptadecan-1-ol

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

Refernces

• 1、 -. "CONJUGATES COMPRISING SELF-IMMOLATIVE GROUPS AND METHODS RELATED THERETO". . . Retrieved 2017/06/27.
• 2、 -. "BCR-ABL TYROSINE-KINASE LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME". . . Retrieved 2015/07/23.