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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
NACRES:
NA.22
PubChem Substance ID:
329765726
UNSPSC Code:
12352003
MDL number:
MFCD19705418
Form:
liquid
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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

Application

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.
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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

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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Articles

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Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

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Global Trade Item Number

SKUGTIN
745073-100MG04061832889436
745073-25MG04061833441039