Acetylthiomethyl-diphenylphosphine borane complex

• CAS: 446822-71-5
• Catalog Number: ACM446822715-1
• Category: Other Products
• Molecular Weight: 288.15
• Molecular Formula: C₁₅H₁₈BOPS
• Synonyms: AGN-PC-005LSK, boron;S-(diphenylphosphanylmethyl) ethanethioate, Acetylthiomethyl-diphenylphosphine borane complex, 446822-71-5
• IUPAC Name: boron;S-(diphenylphosphanylmethyl) ethanethioate
• Canonical SMILES: [B].CC(=O)SCP(C1=CC=CC=C1)C2=CC=CC=C2
• InChI: InChI=1S/C15H15OPS.B/c1-13(16)18-12-17(14-8-4-2-5-9-14)15-10-6-3-7-11-15;/h2-11H,12H2,1H3
• InChI Key: WOWHSIZUGNRROK-UHFFFAOYSA-N
• Melting Point: 52-55° C
• 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.
• Storage: 2-8°C storage
• Complexity: 239
• Covalently-Bonded Unit Count: 2
• Exact Mass: 285.06700
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Heavy Atom Count: 19
• Monoisotopic Mass: 285.067g/mol
• Rotatable Bond Count: 5
• Topological Polar Surface Area: 42.4A^2