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761540

Sigma-Aldrich

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

Sinônimo(s):

DBCO-NH2, DBCO-amine

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About This Item

Fórmula empírica (Notação de Hill):
C18H16N2O
Número CAS:
1255942-06-3
Peso molecular:
276.33
Número MDL:
MFCD22380759
Código UNSPSC:
12352116
ID de substância PubChem:
329766557
NACRES:
NA.22

Nível de qualidade

100

forma

solid

adequação da reação

reaction type: click chemistry
reagent type: linker

pf

86-96 °C

grupo funcional

amine

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

OCCYFTDHSHTFER-UHFFFAOYSA-N

Descrição geral

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.

Aplicação

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
MKCQ7517
MKCQ0030
MKCP5919
MKCN9220
MKCL6572

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Artigos

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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