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Sigma-Aldrich

Dibenzocyclooctyne-acid

95%, storage temp.:-20°C

Synonym(s):

DBCO-Acid

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About This Item

Empirical Formula (Hill Notation):
C21H19NO3
Molecular Weight:
333.38
MDL number:
MFCD22380737
UNSPSC Code:
12352106
PubChem Substance ID:
329766553
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

118-125 °C

functional group

carboxylic acid

storage temp.

−20°C

SMILES string

O=C(CCCCC(O)=O)N1CC2=C(C=CC=C2)C#CC3=C1C=CC=C3

InChI

1S/C21H19NO3/c23-20(11-5-6-12-21(24)25)22-15-18-9-2-1-7-16(18)13-14-17-8-3-4-10-19(17)22/h1-4,7-10H,5-6,11-12,15H2,(H,24,25)

InChI key

NIRLBCOFKPVQLM-UHFFFAOYSA-N

General description

Acid functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne click chemistry reactions. This azadibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.

Application

Dibenzocyclooctyne-acid may be used for the surface modification of eight-arm poly(ethylene glycol), to make it susceptible to strain promoted alkyne-azide cycloaddition (SPAAC) with PEG-bis-azide leading to the formation of hydrogels. These hydrogels are useful for protein immobilization.

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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