15-Azido-4,7,10,13-tetraoxapentadecanoic acid Chemical Properties

storage temp. 

-20°C

solubility 

DMSO : 100 mg/mL (343.29 mM; Need ultrasonic)

form 

Liquid

color 

Colorless to Pale Yellow

Appearance

yellowy liquid

InChI

InChI=1S/C11H21N3O6/c12-14-13-2-4-18-6-8-20-10-9-19-7-5-17-3-1-11(15)16/h1-10H2,(H,15,16)

InChIKey

BODPHGOBXPGJKO-UHFFFAOYSA-N

SMILES

O(CCOCCC(=O)O)CCOCCOCCN=[N+]=[N-]

Safety Information

WGK Germany 

WGK 3

HS Code 

29270000

Storage Class

11 - Combustible Solids

15-Azido-4,7,10,13-tetraoxapentadecanoic acid Usage And Synthesis

Description

Azido-PEG4-acid is a very popular PEG reagent containing an azide group with a terminal carboxylic acid. The hydrophilic PEG spacer increases solubility in aqueous media. The azide group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Chemical Properties

Light yellow to colorless thick liquid

Uses

Azido-PEG4-Acid is amine- or phosphine-reactive building block used to derivative primary amines for ligation to alkyne-tagged molecules.

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent
reaction type: click chemistry

Synthesis

Tert-butyl 15-azido-4,7,10,13-tetraoxopentadecanoate (0.22 g; 0.63 mmol) was dissolved in pure DCM (5 mL) and TFA (5 mL) was added. The solution was stirred at room temperature for 1.5 hours. Next, the volatile compounds were removed in vacuo, the residue was dissolved in diethyl ether (10 mL) and the solvent was evaporated (repeated 2 times). The solution was concentrated to dryness. 15-Azido-4,7,10,13-tetraoxapentadecanoic acid in the form of a colorless oil was obtained (0.18 g; 0.62 mmol; 98%).

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