936375
DBCO Acid
≥95%
Synonym(s):
11,12-Didehydro-γ-oxodibenz[b,f]azocine-5(6H)-butanoic acid (ACI), Dibenz[b,f]azocine-5(6H)-butanoic acid, 11,12-didehydro-γ-oxo- (ACI)
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About This Item
Empirical Formula (Hill Notation):
C19H15NO3
CAS Number:
Molecular Weight:
305.33
NACRES:
NA.22
UNSPSC Code:
12352106
MDL number:
Product Name
DBCO Acid, ≥95%
SMILES string
OC(CCC(N1CC2=CC=CC=C2C#CC3=CC=CC=C13)=O)=O
InChI
InChI=1S/C19H15NO3/c21-18(11-12-19(22)23)20-13-16-7-2-1-5-14(16)9-10-15-6-3-4-8-17(15)20/h1-8H,11-13H2,(H,22,23)
assay
≥95%
form
powder or crystals
color
white to off-white
mp
163-164 °C
storage temp.
−20°C
Quality Level
Application
DBCO Acid is a bifunctional building block comprising of an acid terminus useful for reaction with amine containing linkers in presence of activators such as EDC or HATU and a dibenzocyclooctyne (DBCO) terminus useful for copper-free click chemistry.
Features and Benefits
DBCO compounds react with azides without need of Cu(I) catalyst due to the strained nature of alkyne resulting in formation of fast and stable triazole linkage.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Copper-free click chemistry in living animals
Chang P V, et al.
Proceedings of the National Academy of Sciences of the USA, 107, 1821-1826 (2010)
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
Rostovtsev V V, et al.
Angewandte Chemie (International ed. in English), 41, 2596-2599 (2002)
Pamela V Chang et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(5), 1821-1826 (2010-01-19)
Chemical reactions that enable selective biomolecule labeling in living organisms offer a means to probe biological processes in vivo. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
Vsevolod V Rostovtsev et al.
Angewandte Chemie (International ed. in English), 41(14), 2596-2599 (2002-08-31)
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