761540

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

• Synonym(s): DBCO-NH₂, DBCO-amine
• 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

Properties

• Quality Level: 100
• assay: ≥94.5 %
• 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable