765953

Sigma-Aldrich

1,11-Diazido-3,6,9-trioxaundecane

Synonym(s):
Azido-PEG3-azido, Bis-PEG3-Azide
Empirical Formula (Hill Notation):
C8H16N6O3
CAS Number:
Molecular Weight:
244.25
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

reaction suitability

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

refractive index

n20/D 1.470

bp

163-196 °C/760 mmHg

density

1.170 g/mL at 25 °C

storage temp.

−20°C

SMILES string

[N-]=[N+]=NCCOCCOCCOCCN=[N+]=[N-]

InChI

1S/C8H16N6O3/c9-13-11-1-3-15-5-7-17-8-6-16-4-2-12-14-10/h1-8H2

InChI key

SFMMXKLNFMIUCH-UHFFFAOYSA-N

Application

Homobifunctional PEG azide click chemistry linker. Azide functional groups will react via a copper catalyzed or strain promoted 1,3-dipolar cycloaddition click reaction with terminal alkynes and cyclooctyne derivatives to yield a stable triazole linkage.
1,11-Diazido-3,6,9-trioxaundecane may be used to synthesize:
  • 1,11-bis[4-(pyren-1-ylmethoxymethyl)-1H-1,2,3-triazole-1-yl]-3,6,9-trioxaundecane, a fluorogenic chemosensor that can selective detect Hg2+ and Ag+ ions in aqueous methanol solution
  • 1-amino-11-azido-3,6,9-trioxaundecane, an intermediate to synthesize tetraethylene glycol based bidentate ligand functionalized with dihydrolipoic acid and biotin (DHLA-TEG-biotin)

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Highly Selective Fluorescent Sensors for Hg2+ and Ag+ Based on Bis?triazole?Coupled Polyoxyethylenes in MeOH Solution.
Hung HC, et al.
European Journal of Organic Chemistry, 2009(36), 6360-6366 (2009)
Design of biotin-functionalized luminescent quantum dots.
Susumu K, et al.
BioMed Research International (2007)
Tilman Läppchen et al.
European journal of medicinal chemistry, 89, 279-295 (2014-12-03)
Calixarene 0118 is a potent anti-angiogenic agent that effectively inhibited tumor growth in preclinical studies, and is currently being evaluated in a phase I clinical trial. We have designed two close mimetics of calixarene 0118 containing a terminal alkynyl-functional group...

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