Bicyclononyne

BCN, also known as bicyclo[6.1.0]non-4-yne, is a copper-free click chemistry probe that enables highly efficient and completely orthogonal bioconjugation to complex macromolecules including peptides, nucleic acids and proteins, including monoclonal antibodies.^[1] The most recent and powerful application of this technology has been in the field of antibody-drug conjugates which results in targeted cancer therapeutics that have an improved therapeutic index, meaning they are more effective and better tolerated.^[2] BCN is well-suited for aqueous bioconjugations due to its high reactivity with its azide counterpart and its high hydrophilicity, relative to other metal-free click chemistry probes.^[3]

Bicyclononyne

Names
IUPAC name bicyclo[6.1.0]non-4-yne
Identifiers
CAS Number	1415580-17-4 Y
3D model (JSmol)	Interactive image
ChemSpider	67177330
PubChem CID	14201804
InChI Key: QDNSAFCVPAMWCJ-UHFFFAOYSA-N InChI=1S/C9H12/c1-2-4-6-9-7-8(9)5-3-1/h8-9H,3-7H2
SMILES C1CC2CC2CCC#C1
Properties
Chemical formula	C9H12
Molar mass	120.195 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

BCN, with free hydroxymethyl group