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670359 Sigma-Aldrich

Acetylthiomethyl-diphenylphosphine borane complex


  • CAS Number 446822-71-5

  • Empirical Formula (Hill Notation) C15H18BOPS

  • Molecular Weight 288.15

  •  PubChem Substance ID 329760266

  •  NACRES NA.22



Related Categories Catalysis and Inorganic Chemistry, Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper-Free Click Chemistry,
assay   ≥98.0%
reaction suitability   reaction type: click chemistry
  reagent type: ligand
reaction type: Staudinger Reaction
mp   52-55 °C
storage temp.   2-8°C
SMILES string   B.CC(=O)SCP(c1ccccc1)c2ccccc2
InChI   1S/C15H15OPS.BH3/c1-13(16)18-12-17(14-8-4-2-5-9-14)15-10-6-3-7-11-15;/h2-11H,12H2,1H3;1H3



• Traceless Staudinger ligation reagent with borane protecting group.
• The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine.
• After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.
• Used in the synthesis of cyclic peptides.
Acetylthiomethyl-diphenylphosphine borane complex Ligation with DABCO


1 g in glass bottle

250 mg in glass bottle

Bottomless glass bottle. Contents are inside inserted fused cone.

Legal Information

Sold under license for research and development purposes only. US Patent 6,974,884 and related patents apply

Safety & Documentation

Safety Information

GHS07  GHS07
Signal word 
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Protocols & Articles


Azide Building Blocks for Chemical Ligation

Chemoselective ligation strategies are a key success factor for chemical biology research. Ligation techniques open pathways to fully synthetic large peptides and even proteins. They have proven to b...
Chemfiles Volume 10 Article 2
Keywords: 1,3-Dipolar cycloaddition, Acetylations, Building blocks, Catalysis, Chemical biology, Cyclizations, Cycloadditions, Eliminations, Immobilization, Metal organic frameworks, Molecular probes, Nanotubes, Oxidations, Peptide synthesis, Pharmaceutical, Purification, Reductions, Staudinger Reaction

Raines Group – Products available at Aldrich from the Raines Laboratory

From our library of Articles, Sigma-Aldrich presents Raines Group – Products available at Aldrich from the Raines Laboratory
Keywords: Cancer, Chemical biology, Clinical, Enzymology, Peptide synthesis

Staudinger Ligation - Aldrich ChemFiles 2008, 8.1, 7.

The reaction between an azide and a phosphine forming an aza-ylide was discovered almost a century ago by Nobel Prize laureate Herrmann Staudinger. It has found widespread application in chemical syn...
Matthias Junkers
Aldrich ChemFiles 2008, 8.1, 7.
Keywords: Amidations, Catalysis, Chemfiles, Cyclizations, Eliminations, Esterifications, Glycosylations, Iodinations, Methods, Molecular probes, Peptide synthesis, Reductions, Solid phase peptide synthesis, Staudinger Reaction, Staudinger Reduction, Type, Wittig Reaction

Traceless Staudinger Ligation

Although the previously described methods for Staudinger ligations work well even in biological environments, a modification forming a native amide bond without leaving the unnatural phosphine oxide ...
Matthias Junkers
Aldrich ChemFiles 2008, 8.1, 9.
Keywords: Catalysis, Chemfiles, Methods, Peptide synthesis, Solid phase peptide synthesis

Peer-Reviewed Papers


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