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Merck
CN

745073

N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane

for Copper-free Click Chemistry

Synonym(s):

(1α,8α,9β)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate, BCN-amine

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About This Item

Empirical Formula (Hill Notation):
C17H28N2O4
CAS Number:
1263166-93-3
Molecular Weight:
324.42
MDL number:
MFCD19705418
UNSPSC Code:
12352003
PubChem Substance ID:
329765726
NACRES:
NA.22

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Quality Level

100

form

liquid

composition

carbon content, 62.94%
hydrogen content, 8.70%
nitrogen content, 8.63%

reaction suitability

reaction type: click chemistry
reagent type: linker

solubility

water: 1.5 g/L

density

1.14  g/cm3 at 20  °C

functional group

amine

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@]12CCC#CCC[C@]1([H])[C@@H]2COC(NCCOCCOCCN)=O

InChI

1S/C17H28N2O4/c18-7-9-21-11-12-22-10-8-19-17(20)23-13-16-14-5-3-1-2-4-6-15(14)16/h14-16H,3-13,18H2,(H,19,20)/t14-,15+,16-

InChI key

YZGOWXGENSKDSE-MUJYYYPQSA-N

Related Categories

Application

Amine functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This strained cyclooctyne will react with azide functionalized compounds or biomolecules without the need for a copper catalyst to result in a stable triazole linkage.
N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane may be used to functionalize hyaluronic acid with bicyclo[6.1.0]nonyne (BCN) for the development of responsive HA-based physical hydrogels with tunable properties.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7535
BCCL6140
BCCK8171
BCCJ9740
BCCH9737

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Orientation of llama antibodies strongly increases sensitivity of biosensors
Trilling AK, et al.
Biosensors And Bioelectronics, 60, 130-136 (2014)
Comparison of strain-promoted alkyne-azide cycloaddition with established methods for conjugation of biomolecules to magnetic nanoparticles
Gruttner C, et al.
IEEE Transactions on Magnetics, 49(1), 172-176 (2013)
Jonathan Cortese et al.
Stroke, 52(2), 677-686 (2021-01-09)
Beyond aneurysmal occlusion, metallic flow diverters (FDs) can induce an adverse endovascular reaction due to the foreignness of metal devices, hampering FD endothelialization across the aneurysm neck, and arterial healing of intracranial aneurysms. Here, we evaluated the potential benefits of
Folding driven self-assembly of a stimuli-responsive peptide-hyaluronan hybrid hydrogel.
Seleg?rd R, et al.
Scientific Reports, 7 (2017)
Christopher Aronsson et al.
Biofabrication, 12(3), 035031-035031 (2020-05-20)
Hydrogels are used in a wide range of biomedical applications, including three-dimensional (3D) cell culture, cell therapy and bioprinting. To enable processing using advanced additive fabrication techniques and to mimic the dynamic nature of the extracellular matrix (ECM), the properties
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