| Identification | Back Directory | [Name]
Dibenzocyclooctyne-aMine | [CAS]
1255942-06-3 | [Synonyms]
DBCO-NH2
DBCO-amine
DBCO-(CH2)2-NH2
ADIBO-CH2CH2NH2·TFA
DBCO-(CH2)2-NH2.TFA
DBCO-(CH2)3-NH2.TFA
Dibenzocyclooctyne-amine
DBCO-Amine
(DBCO amine)
Azadibenzocylooctyne-amine
Azadibenzocyclooctyne-amine
Azadibenzocyclooctyne-(CH2)2-amine TFA
Dibenzocyclooctyne-aMine for Copper-free Click CheMistry
Dibenzocyclooctyne-amine (This product is unavailable in the U.S.)
1-Propanone, 3-amino-1-(11,12-didehydrodibenz[b,f]azocin-5(6H)-yl)-
3-amino-1-{2-azatricyclo[10.4.0.0?,?]hexadeca-1(16),4,6,8,12,14-hexaen-10-yn-2-yl}propan-1-one | [Molecular Formula]
C18H16N2O | [MDL Number]
MFCD22380759 | [MOL File]
1255942-06-3.mol | [Molecular Weight]
276.33 |
| Chemical Properties | Back Directory | [Melting point ]
86-96°C | [Boiling point ]
549.9±50.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: Sparingly soluble: 1-10 mg/ml
Ethanol: Sparingly soluble: 1-10 mg/ml | [form ]
Solid | [pka]
8.81±0.10(Predicted) | [color ]
Yellow to Orange | [Appearance]
White or light yellow solid | [InChI]
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 | [InChIKey]
PQFQVUMDOWUGMK-CHMOPDDRSA-N | [SMILES]
C(N1CC2=CC=CC=C2C#CC2=CC=CC=C12)(=O)CCN |
| Hazard Information | Back Directory | [Description]
DBCO-amine is a simple building block containing a DBCO moiety and will add minimal spacer to the modified molecules. In the presence of activators such as EDC or HATU, this reagent can be used to derivatize carboxyl groups or activated esters (e.g. The NHS ester) through a stable amide bond. DBCO is commonly used for copper-free Click Chemistry reactions. | [Uses]
Azadibenzocyclooctyne amine is a carbonyl reactive reagent used to incorporate ADIBO into organic compounds, surfaces or particlesAzadibenzocyclooctyne amine is widely useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. It reacts with azide functionalized compounds or bimolecules to give stable triazole linkage without a need for a Cu(I) catalyst. | [reaction suitability]
reaction type: click chemistry
reagent type: linker | [IC 50]
Cleavable Linker | [Properties and Applications]
DBCO-amine is an aza-dibenzocyclooctyne (DBCO) product used for strain-promoted azide-alkyne cycloaddition (SPAAC, also known as “copper-free click chemistry”). The DBCO moiety reacts selectively with azides via SPAAC to form stable triazole linkages. The amine terminus of the molecule reacts with carboxylic acids and their active esters to form stable amide bonds. Insoluble in water, DBCO-amine is slightly soluble to sparingly soluble in most organic solvents. It recommends dimethylsulfoxide (DMSO), N, N’-dimethylformamide (DMF), or N, N’-dimethylacetamide (DMAC) as solvents for this product. DBCO-amine is relatively insensitive to bases and can be used in the presence of aqueous bases. This product is acid-sensitive. It should not be subjected to pH <5 during reaction or workup. The product should always be stored at -20°C when not in use. | [References]
[1] YAMAGISHI K, SAWAKI K, MURATA A, et al. A Cu-free clickable fluorescent probe for intracellular targeting of small biomolecules†[J]. Chemical Communications, 2015, 37: 7879-7882. DOI: 10.1039/c4cc09947h |
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