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745073

Sigma-Aldrich

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

Key Documents

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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

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This Item
900610QBD1056745548
N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane for Copper-free Click Chemistry

Sigma-Aldrich

745073

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

Hydroxyl di-benzophenone (PEG)3 alkyne

Sigma-Aldrich

900610

Hydroxyl di-benzophenone (PEG)3 alkyne

Azido-dPEG ®4-TFP ester

Sigma-Aldrich

QBD10567

Azido-dPEG ®4-TFP ester

Lindane PESTANAL®, analytical standard

Supelco

45548

Lindane

reaction suitability

reaction type: click chemistry, reagent type: linker

reaction suitability

reaction type: click chemistry

reaction suitability

reaction type: click chemistry, reagent type: cross-linking reagent
reaction type: click chemistry

reaction suitability

-

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

solubility

water: 1.5 g/L

solubility

-

solubility

-

solubility

H2O: 8.35 g/L at 25 °C

form

liquid

form

powder or crystals

form

solid or viscous liquid

form

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

density

1.14  g/cm3 at 20  °C

density

-

density

-

density

-

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.[1]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

10 - Combustible liquids

wgk_germany

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)
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
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
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