Acetylthiomethyl-diphenylphosphine borane complex

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Acetylthiomethyl-diphenylphosphine borane complex Basic information
Product Name:Acetylthiomethyl-diphenylphosphine borane complex
Synonyms:Acetylthiomethyl-diphenylphosphine borane complex;Acetylthiomethyl-diphenylphosphine borane complex >=98.0%
CAS:446822-71-5
MF:C15H18BOPS
MW:288.157
EINECS:
Product Categories:Catalysis and Inorganic Chemistry;Chemical Synthesis;Chemical Ligation;Other LigandsSpecialty Synthesis;Staudinger Ligation
Mol File:446822-71-5.mol
Acetylthiomethyl-diphenylphosphine  borane  complex Structure
Acetylthiomethyl-diphenylphosphine borane complex Chemical Properties
Melting point 52-55 °C
storage temp. 2-8°C
form solid
InChI1S/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
InChIKeyMXPNVFCCEGQGEN-UHFFFAOYSA-N
SMILESB.CC(=O)SCP(c1ccccc1)c2ccccc2
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26
WGK Germany 3
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
Acetylthiomethyl-diphenylphosphine borane complex Usage And Synthesis
UsesTraceless 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.
Uses
  • 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.
reaction suitabilityreaction type: click chemistry
reagent type: ligand
reaction type: Staudinger Reaction
Acetylthiomethyl-diphenylphosphine borane complex Preparation Products And Raw materials
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