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09658

Sigma-Aldrich

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:
94790-35-9
Molecular Weight:
280.58
Beilstein:
7896715
MDL number:
MFCD01862891
UNSPSC Code:
12352101
PubChem Substance ID:
329748788
NACRES:
NA.22

Quality Level

100

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

Related Categories

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 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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL5040
BCCH2097
BCCJ6065
BCCD5111
BCCD1065

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Progress towards the synthesis of piperazimycin A: synthesis of the non-proteogenic amino acids and elaboration into dipeptides
Kennedy JP and Lindsley CW
Tetrahedron Letters, 51(18), 2493-2496 (2010)
Judit Tulla-Puche et al.
Bioconjugate chemistry, 19(10), 1968-1971 (2008-09-23)
Prodrugs are increasingly used as delivery vehicles for pharmaceutical agents that present solubility and/or pharmacokinetic/metabolic issues. In the course of the development of prodrugs for the antitumoral agent thiocoraline, standard coupling reagents and procedures failed to provide the desired target
Ayman El-Faham, et al
European Journal of Organic Chemistry, 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)
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