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94624

Sigma-Aldrich

S-(1-Oxido-2-pyridyl)-N,N,N′,N′-tetramethylthiuronium hexafluorophosphate

≥95.0% (NMR)

Synonym(s):

N,N,N′,N′-Tetramethyl-S-(1-oxido-2-pyridyl)thiuronium hexafluorophosphate, S-(2-Pyridyl)-N,N,N′,N′-tetramethylthiuronium N-oxide hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C10H16F6N3OPS
CAS Number:
Molecular Weight:
371.28
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Assay

≥95.0% (NMR)

form

crystals

reaction suitability

reaction type: Coupling Reactions

mp

120-125 °C

application(s)

peptide synthesis

functional group

amine
thiourea

storage temp.

−20°C

SMILES string

F[P-](F)(F)(F)(F)F.CN(C)\C(=[S+]\c1cccc[n+]1[O-])N(C)C

InChI

1S/C10H16N3OS.F6P/c1-11(2)10(12(3)4)15-9-7-5-6-8-13(9)14;1-7(2,3,4,5)6/h5-8H,1-4H3;/q+1;-1

InChI key

UCOGEMMJHLHOAW-UHFFFAOYSA-N

Application

Reagent for:
Synthesis of inhibitors for PAD1, 3, and 4
Synthesis of enantiomerically pure vinylcyclopropylboronic esters
Synthesis of enantiomerically pure cyclopropane building blocks
Camphor-derived chiral auxiliary for hydroxyalkyl radicals
Solution and solid-phase coupling
Conversion of carboxylic acids to Weinreb amides and N-methoxy or N-benzoxy amides

Other Notes

Very reactive peptide coupling reagent

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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F. Albericio et al.
Tetrahedron, 57, 9607-9607 (2001)
2-Mercaptopyridone 1-Oxide-Based Uronium Salts: New Peptide Coupling Reagents(1)(,)(2).
Miguel A. Bailén et al.
The Journal of organic chemistry, 64(24), 8936-8939 (2001-10-25)

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