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  • 742678 - (1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethanol

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742678 Sigma-Aldrich

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethanol

for Copper-free Click Chemistry

Synonym: (1α,8α,9β)-Bicyclo[6.1.0]non-4-yne-9-methanol, endo-9-Hydroxymethylbicyclo[6.1.0]non-4-yne, BCN-OH

  • CAS Number 1263166-90-0

  • Empirical Formula (Hill Notation) C10H14O

  • Molecular Weight 150.22

  •  Beilstein/REAXYS Number 21037713

  •  MDL number MFCD26142970

  •  PubChem Substance ID 329765586

  •  NACRES NA.22

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper-Free Click Chemistry, Cyclooctynes for Cu(I)-free Cycloadditions More...
Quality Level   100
composition   carbon content, 79.96%
  hydrogen content, 9.39%
reaction suitability   reaction type: click chemistry
storage temp.   −20°C
SMILES string   [H][C@@]12[C@@]([C@H]2CO)([H])CCC#CCC1
InChI   1S/C10H14O/c11-7-10-8-5-3-1-2-4-6-9(8)10/h8-11H,3-7H2/t8-,9+,10-
InChI key   NSVXZMGWYBICRW-ILWJIGKKSA-N

Description

Application

Alcohol 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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

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.1 The absence of exogenous me...
Keywords: 1,3-Dipolar cycloaddition, Catalysis, Click chemistry, Cycloadditions, Pharmaceutical, Positron Emission Tomography

Peer-Reviewed Papers
15

References

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