Skip to Content
Merck
All Photos(3)

Documents

761540

Sigma-Aldrich

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

Synonym(s):

DBCO-NH2, DBCO-amine

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C18H16N2O
CAS Number:
1255942-06-3
Molecular Weight:
276.33
MDL number:
MFCD22380759
UNSPSC Code:
12352116
PubChem Substance ID:
329766557
NACRES:
NA.22

Quality Level

100

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

86-96 °C

functional group

amine

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

General description

Dibenzocyclooctyne-amine (DBCO-NH2), is a heterobifunctional linker containing a DBCO moiety commonly used for the site-specific functionalization of nanobodies, enabling the addition of reactive DBCO groups for subsequent click chemistry reactions.

Application

Dibenzocyclooctyne-amine can be used as a :
  • Linker to link azide-containing functional groups. It facilitates the formation of linkages through Strain-promoted azide-alkyne cycloaddition reactions (SPAAC)
  • Reagent in the synthesis of N-heterocyclic carbene metal thiolates. It functionalizes the metal complexes and increases their reactivity in the strain-promoted alkyne–azide cycloaddition (SPAAC) reactions
  • 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)
Picomolar SARS-CoV-2 neutralization using multi-arm PEG nanobody constructs
A Moliner-Morro, et al.
Biomolecules, 10, 1661-1661 (2020)
View All Related Papers

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.

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.

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.

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.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service