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670359 Aldrich

Acetylthiomethyl-diphenylphosphine borane complex

≥98.0%

  • CAS Number 446822-71-5

  • Empirical Formula (Hill Notation) C15H18BOPS

  • Molecular Weight 288.15

  •  PubChem Substance ID 329760266

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper-Free Click Chemistry,
InChI Key   MXPNVFCCEGQGEN-UHFFFAOYSA-N
assay   ≥98.0%
mp   52-55 °C
storage temp.   2-8°C

Description

Packaging

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

Application

• 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

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis


Screeing simplified
Protocols & Articles

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, 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
15

References

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