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(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate

for Copper-free Click Chemistry

N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-succinimidyl ester, BCN-NHS
Empirical Formula (Hill Notation):
CAS Number:
Molecular Weight:
PubChem Substance ID:

Quality Level




carbon content, 61.85%
hydrogen content, 5.88%
nitrogen content, 4.81%

reaction suitability

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

storage temp.


SMILES string




InChI key



(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate may be used to functionalize the primary amines of the lysine residue of recombinant elastin-like proteins (ELPs). These functionalized ELPs quickly undergo cross-linking via bio-orthogonal strain-promoted azide-alkyne cycloaddition reactions to form hydrogels with high gelation kinetics and tunable mechanics, making them useful biomaterials for cell encapsulation.{67
It may also be used to synthesize bicyclononyne functionalized poly(ethylene glycol) polymer coatings with anti-fouling properties towards protein adhesion and cell adhesion for supramolecular ureidopyrimidinone (UPy) based materials.
Succinimidyl ester/NHS functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. 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.


Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non Combustible Solids



Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

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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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