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761540

Sigma-Aldrich

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

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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

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

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This Item
760668764019762040
vibrant-m

761540

Dibenzocyclooctyne-amine

vibrant-m

760668

Dibenzocyclooctyne-maleimide

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

form

solid

form

solid

form

paste

form

solid

mp

86-96 °C

mp

-

mp

-

mp

240-260 °C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

functional group

amine

functional group

maleimide

functional group

NHS ester

functional group

-

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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