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Acetylthiomethyl-diphenylphosphine borane complex

Catalog Number
ACM446822715
Product Name
Acetylthiomethyl-diphenylphosphine borane complex
CAS
446822-71-5
  • Product Overview
  • Usage
Synonyms
AGN-PC-005LSK, boron;S-(diphenylphosphanylmethyl) ethanethioate, Acetylthiomethyl-diphenylphosphine borane complex, 446822-71-5
IUPAC Name
boron;S-(diphenylphosphanylmethyl) ethanethioate
Molecular Weight
288.15
Molecular Formula
C₁₅H₁₈BOPS
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
Purity
96%
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
Application
The Acetylthiomethyl-diphenylphosphine borane complex serves as a traceless Staudinger ligation reagent that includes a borane protecting group to enhance the stability of phosphine by preventing its oxidation. This protective borane group can be easily detached under mild basic or acidic conditions to release the active form of phosphine. Once the complex reacts with an azide, the phosphine component is removed in the presence of water, leading to the formation of a natural amide bond. This property makes it particularly useful for the synthesis of cyclic peptides, where maintaining the integrity of the amide bond is crucial.
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