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Sigma-Aldrich

O-(2-Aminoethyl)-O′-(2-azidoethyl)pentaethylene glycol

≥90% (oligomer purity)

Synonym(s):

Azido-PEG-amine (n=6)

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About This Item

Empirical Formula (Hill Notation):
C14H30N4O6
CAS Number:
957486-82-7
Molecular Weight:
350.41
MDL number:
MFCD03453240
UNSPSC Code:
12352200
PubChem Substance ID:
57652623
NACRES:
NA.22

Assay

≥90% (oligomer purity)

form

liquid

reaction suitability

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

functional group

amine
azide

storage temp.

2-8°C

SMILES string

NCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

InChI

1S/C14H30N4O6/c15-1-3-19-5-7-21-9-11-23-13-14-24-12-10-22-8-6-20-4-2-17-18-16/h1-15H2

InChI key

VCQSTKKJKNUQBI-UHFFFAOYSA-N

Application

O-(2-Aminoethyl)-O′-(2-azidoethyl)pentaethylene glycol can be used:
  • As a reactant for the synthesis of thin films of azide functionalized poly(L-glutamic acid) for drug delivery.
  • For the synthesis of curcumin monoazide derivatives for fabricating biologically active curcumin conjugates.
  • To modify the surface of TiO2 nanoparticles to attach DNA strands for photocatalytic reduction of CO2.
  • For the conjugation of poly(ethylene glycol) (PEG) with toll-like receptor 7 (TLR7) to improve its pharmaceutical properties.

O-(2-Aminoethyl)-O′-(2-azidoethyl)pentaethylene glycol has been used in the synthesis of Alexa568-azide, a fluorescent azide that can undergo click staining reaction with 5-ethynyluridine-labeled cellular RNA.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of monofunctional curcumin derivatives, clicked curcumin dimer, and a PAMAM dendrimer curcumin conjugate for therapeutic applications.
Shi W, et al.
Organic Letters, 9(26), 5461-5464 (2007)
Exploring RNA transcription and turnover in vivo by using click chemistry.
Jao CY & Salic A.
Proceedings of the National Academy of Sciences of the USA, 105(41), 15779-15784 (2008)
Low-fouling, biofunctionalized, and biodegradable click capsules.
Ochs CJ, et al.
Biomacromolecules, 9(12), 3389-3396 (2008)
DNA for Assembly and Charge Transport Photocatalytic Reduction of CO2.
Ma K, et al.
Advanced Sustainable Systems, 2(4), 1700156-1700156 (2018)
Metabolic labeling and direct imaging of choline phospholipids in vivo.
Jao CY, et al.
Proceedings of the National Academy of Sciences of the USA, 106(36), 15332-15337 (2009)
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