Skip to Content
Merck
All Photos(1)

Documents

761516

Sigma-Aldrich

Dibenzocyclooctyne-acid

95%, storage temp.:-20°C

Synonym(s):

DBCO-Acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ratiometric Fluorescence Azide?Alkyne Cycloaddition for Live Mammalian Cell Imaging.
Fu H, et al.
Analytical Chemistry, 87(22), 11332-11336 (2015)
Chen Guo et al.
Acta biomaterialia, 56, 80-90 (2017-04-10)
Hydrogels are facile architectures for the controlled presentation of proteins with far-reaching applications, from fundamental biological studies in three-dimensional culture to new regenerative medicine and therapeutic delivery strategies. Here, we demonstrate a versatile approach for spatially-defined presentation of engineered proteins
Flexible synthesis of cationic peptide?porphyrin derivatives for light-triggered drug delivery and photodynamic therapy.
Dondi R, et al.
Organic & Biomolecular Chemistry, 14(48), 11488-11501 (2016)
Seyed Mohammad Mahdi Dadfar et al.
Small (Weinheim an der Bergstrasse, Germany), 14(21), e1800131-e1800131 (2018-04-24)
Different types of click chemistry reactions are proposed and used for the functionalization of surfaces and materials, and covalent attachment of organic molecules. In the present work, two different catalyst-free click approaches, namely azide-alkyne and thiol-alkyne click chemistry are studied
Jianwen Xu et al.
Chemistry, an Asian journal, 6(10), 2730-2737 (2011-09-29)
Strategies to encapsulate cells in cytocompatible three-dimensional hydrogels with tunable mechanical properties and degradability without harmful gelling conditions are highly desired for regenerative medicine applications. Here we reported a method for preparing poly(ethylene glycol)-co-polycarbonate hydrogels through copper-free, strain-promoted azide-alkyne cycloaddition
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service