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23955

Sigma-Aldrich

Chlorodipyrrolidinocarbenium hexafluorophosphate

≥97.5% (CHN)

Synonym(s):

N,N,N′,N′-Bis(tetramethylene)chloroformamidinium hexafluorophosphate, Chloro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate, PyClU

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About This Item

Linear Formula:
C9H16N2Cl · PF6
CAS Number:
Molecular Weight:
332.65
Beilstein/REAXYS Number:
7898575
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97.5% (CHN)

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

153-156 °C

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

F[P-](F)(F)(F)(F)F.Cl\C(N1CCCC1)=[N+]2/CCCC2

InChI

1S/C9H16ClN2.F6P/c10-9(11-5-1-2-6-11)12-7-3-4-8-12;1-7(2,3,4,5)6/h1-8H2;/q+1;-1

InChI key

NHEGCUSBUWGOQM-UHFFFAOYSA-N

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Application

Reactant for:
Enantioselective desymmetrization of meso-asiridines
Peptide coupling
Reagent for:
Heterocyclization of chloroformamidinium salts
Oxidative insertion for palladium and nickel catalyst synthesis

Other Notes

Crystalline and non-hygroscopic peptide coupling reagent, especially for N-methyl amino acids

pictograms

Exclamation mark

signalword

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


Certificates of Analysis (COA)

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J. Coste et al.
Tetrahedron Letters, 32, 1967-1967 (1991)

Articles

The generation of an acid chloride is an obvious way to activate the carboxy group for amide bond formation. However, practical application of acid chlorides in peptide synthesis is restricted, because they are prone to side reactions and racemization.

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