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Merck
CN

09658

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

≥98.0% (T)

Synonym(s):

TCFH

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About This Item

Empirical Formula (Hill Notation):
C5H12ClF6N2P
CAS Number:
Molecular Weight:
280.58
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
7896715
Assay:
≥98.0% (T)
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Quality Level

assay

≥98.0% (T)

reaction suitability

reaction type: Coupling Reactions

mp

99-112 °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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
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)
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)
J. Phillip Kennedy and Craig W. Lindsley
Tetrahedron Letters, 51, 2493-2496 (2010)
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)

Global Trade Item Number

SKUGTIN
235857-100G04061838785268
235857-25G04061838785275
818097005004022536427515
09658-5G04061833354896

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