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936375

Sigma-Aldrich

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:
1353016-70-2
Molecular Weight:
305.33
MDL number:
MFCD28064336
UNSPSC Code:
12352106
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder or crystals

color

white to off-white

mp

163-164 °C

storage temp.

−20°C

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)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000302507
0000302506
0000284561

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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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