(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.


NONH for all modes of transport

WGK Germany


Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

?Click? access to multilayer functionalized Au surface: A terpyridine patterning example.
Materials Science and Engineering, C, 75, 1343-1350 (2017)
Introduction of anti-fouling coatings at the surface of supramolecular elastomeric materials via post-modification of reactive supramolecular additives
Goor OJ, et al.
Polym. Chem., 8(34), 5228-5238 (2017)
Installing an additional emission quenching pathway in the design of iridium (III)-based phosphorogenic biomaterials for bioorthogonal labelling and imaging
Li SPY, et al.
Biomaterials, 103, 305-313 (2016)
Recombinant DNA technology and click chemistry: a powerful combination for generating a hybrid elastin-like-statherin hydrogel to control calcium phosphate mineralization.
Misbah MH, et al.
Beilstein Journal of Nanotechnology, 8, 772-772 (2017)
Bio?Orthogonally Crosslinked, Engineered Protein Hydrogels with Tunable Mechanics and Biochemistry for Cell Encapsulation
Madl CM, et al.
Advances in Functional Materials, 26(21), 3612-3620 (2016)
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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