Merck
All Photos(3)

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

form

solid

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More documents

Quotes and Ordering

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)
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)
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)
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)

Articles

Copper-Free Click Chemistry

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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