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09658

Sigma-Aldrich

Chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate

≥98.0% (T)

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Synonym(s):
TCFH
Empirical Formula (Hill Notation):
C5H12ClF6N2P
CAS Number:
Molecular Weight:
280.58
Beilstein:
7896715
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0% (T)

reaction suitability

reaction type: Coupling Reactions

mp

99-118 °C

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

F[P-](F)(F)(F)(F)F.CN(C)\C(Cl)=[N+](\C)C

InChI

1S/C5H12ClN2.F6P/c1-7(2)5(6)8(3)4;1-7(2,3,4,5)6/h1-4H3;/q+1;-1

InChI key

CUKNPSDEURGZCO-UHFFFAOYSA-N

Application

Chloro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate can be used as a reactant for the synthesis of:
  • Onium salts for use in peptide coupling.
  • Benzotriazole based uranium reagent, a safer replacement for coupling reagents.

It can also be used as a reagent for the synthesis of:
  • Cancer cell cytotoxins.
  • Bioconjugation reagents.

Other Notes

Coupling reagent for peptide synthesis and starting material for preparing other coupling reagents

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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An Efficient Second-Generation Manufacturing Process for the pan-RAF Inhibitor Belvarafenib
Zell, D., et al.
Organic Process Research & Development, 25, 10, 2338-2350 (2021)
A novel family of onium salts based upon isonitroso meldrum's acid proves useful as peptide coupling reagents
El-Faham A, et al.
European Journal of Organic Chemistry, 2010(19), 3641-3649 (2010)
N, N, N′, N′-Tetramethylchloroformamidinium hexafluorophosphate (TCFH), a powerful coupling reagent for bioconjugation
Tulla-Puche J, et al.
Bioconjugate Chemistry, 19(10), 1968-1971 (2008)
TCFH?NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations
Beutner, Gregory et. al.
Organic Letters, 20(14), 4218?4222-4218?4222 (2018)
J. Phillip Kennedy and Craig W. Lindsley
Tetrahedron Letters, 51, 2493-2496 (2010)

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