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761540

Sigma-Aldrich

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

Synonym(s):

DBCO-NH2, DBCO-amine

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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

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)

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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)
Picomolar SARS-CoV-2 neutralization using multi-arm PEG nanobody constructs
A Moliner-Morro, et al.
Biomolecules, 10, 1661-1661 (2020)
Covalently linking CuInS 2 quantum dots with a Re catalyst by click reaction for photocatalytic CO 2 reduction
J Huang, et al.
Dalton Transactions, 47, 10775-10783 (2018)
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