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670359

Sigma-Aldrich

Acetylthiomethyl-diphenylphosphine borane complex

≥98.0%

Synonym(s):

(T-4)-[S-[(Diphenylphosphino-κP)methyl] ethanethioate]trihydroboron

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About This Item

Empirical Formula (Hill Notation):
C15H18BOPS
CAS Number:
446822-71-5
Molecular Weight:
288.15
UNSPSC Code:
12352200
PubChem Substance ID:
329760266
NACRES:
NA.22

assay

≥98.0%

form

solid

reaction suitability

reaction type: click chemistry
reagent type: ligand
reaction type: Staudinger Reaction

mp

52-55 °C

functional group

phosphine

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

InChI key

MXPNVFCCEGQGEN-UHFFFAOYSA-N

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.[1]
  • After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.[2]
  • Used in the synthesis of cyclic peptides.[2]
Acetylthiomethyl-diphenylphosphine borane complex Ligation with DABCO

Packaging

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

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pictograms

Exclamation mark
GHS07

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Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5652V
0000100645
0000092856
0000078637
0000064082

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Matthew B Soellner et al.
The Journal of organic chemistry, 67(14), 4993-4996 (2002-07-06)
The Staudinger ligation of peptides with a C-terminal phosphinothioester and N-terminal azide is an emerging method in protein chemistry. Here, the first Staudinger ligations of nonglycyl azides are reported and shown to proceed both in nearly quantitative yield and with
Michaela Mühlberg et al.
Bioorganic & medicinal chemistry, 18(11), 3679-3686 (2010-05-15)
The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the

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