Propargyl-PEG4-bromide

Base Information

• Chemical Name: Propargyl-PEG4-bromide
• CAS No.: 1308299-09-3
• Molecular Formula: C₁₁H₁₉BrO₄
• Molecular Weight: 295.173
• Mol file: 1308299-09-3.mol

Synonyms:triethylene glycol 2-bromoethyl propargyl ether

Chemical Property of Propargyl-PEG4-bromide

Chemical Property:

• Boiling Point: 334.3±32.0 °C(Predicted)
• Density: 1.269±0.06 g/cm3(Predicted)

Purity/Quality:

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

Propargyl-PEG4-bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Propargyl-PEG4-bromide is a crosslinker that can be used in copper catalyzed azide-alkyne Click Chemistry to form a stable triazole linkage with azides. The bromide (Br) acts as a good leaving group for nucleophilic substitution reactions.

Technology Process of Propargyl-PEG4-bromide

There total 3 articles about Propargyl-PEG4-bromide 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: 95.0%

3,6,9,12-tetraoxapentadec-14-yn-1-ol (87450-10-0) → triethylene glycol 2-bromoethyl propargyl ether (1308299-09-3,2055105-25-2)

Guidance literature:

3,6,9,12-tetraoxapentadec-14-yn-1-ol; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

With carbon tetrabromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201603673

Reference yield:

Tetraethylene glycol (112-60-7) → triethylene glycol 2-bromoethyl propargyl ether (1308299-09-3,2055105-25-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / 1,4-dioxane; toluene; mineral oil / 20 °C

2: pyridine / dichloromethane / 0 - 20 °C

3: potassium bromide / N,N-dimethyl-formamide / 100 °C

With pyridine; sodium hydride; potassium bromide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.2174/157340611794072670

Reference yield:

toluene-4-sulfonic acid 2-{2-[2-(2-ethynyloxyethoxy)-ethoxy]-ethoxy}-ethyl ester (875770-32-4) → triethylene glycol 2-bromoethyl propargyl ether (1308299-09-3,2055105-25-2)

Guidance literature:

With potassium bromide; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.2174/157340611794072670

upstream raw materials:

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

Tetraethylene glycol

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

Downstream raw materials:

(R)-5-((4-(13-(4-amino-2-oxopyrimidin-1(2H)-yl)-2,5,8,11-tetraoxatridecyl)-1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

(R)-tert-butyl 4-(4-(5-((4-(13-(4-amino-2-oxopyrimidin-1(2H)-yl)-2,5,8,11-tetraoxatridecyl)-1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)-2-fluoro phenyl)piperazine-1-carboxylate

(R)-1-(1-(1-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)-1H-1,2,3-triazol-4-yl)-2,5,8,11-tetraoxatridecan-13-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

(R)-tert-butyl 4-(2-fluoro-4-(5-((4-(13-(5-methyl-2,4-dioxo-3,4-dihydro pyrimidin-1(2H)-yl)-2,5,8,11-tetraoxatridecyl)-1H-1,2,3-triazol-1-yl)methyl)-2-oxazolidin-3-yl)phenyl)piperazine-1-carboxylate