761540

Sigma-Aldrich

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

Synonym(s):
DBCO-NH2, DBCO-amine
Empirical Formula (Hill Notation):
C18H16N2O
CAS Number:
Molecular Weight:
276.33
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

reaction suitability

reaction type: click chemistry

mp

86-96 °C

storage temp.

−20°C

SMILES string

NCCC(N1CC2=C(C=CC=C2)C#CC3=C1C=CC=C3)=O

InChI

1S/C18H16N2O/c19-12-11-18(21)20-13-16-7-2-1-5-14(16)9-10-15-6-3-4-8-17(15)20/h1-8H,11-13,19H2

InChI key

OCCYFTDHSHTFER-UHFFFAOYSA-N

Related Categories

Application

Amine functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.

Packaging

10, 100 mg in amber glass bottle

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Steering the azido?tetrazole equilibrium of 4-azidopyrimidines via substituent variation?implications for drug design and azide?alkyne cycloadditions.
Thomann A, et al.
Organic & Biomolecular Chemistry, 13(43), 10620-10630 (2015)
An azide functionalized oligothiophene ligand?A versatile tool for multimodal detection of disease associated protein aggregates.
Johansson LB, et al.
Biosensors And Bioelectronics, 63, 204-211 (2015)
Strained cyclooctyne as a molecular platform for construction of multimodal imaging probes
Sun Y, et al.
Angewandte Chemie (International Edition in English), 54(20), 5981-5984 (2015)
Catalyst-free site-specific surface modifications of nanocrystalline diamond films via microchannel cantilever spotting
Davydova M, et al.
Royal Society of Chemistry Advances, 6(63), 57820-57827 (2016)
Prolonging the circulatory retention of SPIONs using dextran sulfate: in vivo tracking achieved by functionalisation with near-infrared dyes.
Abdollah MR, et al.
Faraday Discussions, 175, 41-58 (2015)
Related Content
Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.
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