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Sigma-Aldrich

(S)-(+)-3-Fluoropyrrolidine hydrochloride

97%

Synonym(s):

(3S)-(+)-3-Fluoropyrrolidine hydrochloride, (3S)-3-Fluoropyrrolidine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C4H8FN · HCl
CAS Number:
136725-53-6
Molecular Weight:
125.57
MDL number:
MFCD04038718
UNSPSC Code:
12352005
PubChem Substance ID:
24882861
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]20/D +8°, c = 1% in methanol

mp

183-187 °C (lit.)

SMILES string

Cl.F[C@H]1CCNC1

InChI

1S/C4H8FN.ClH/c5-4-1-2-6-3-4;/h4,6H,1-3H2;1H/t4-;/m0./s1

InChI key

LENYOXXELREKGZ-WCCKRBBISA-N

Application

(S)-(+)-3-Fluoropyrrolidine hydrochloride can be employed as a building block for the preparation of:
  • Fluorinated pyrrolidine derivatives of cyclohexylglycine amides as potential inhibitors for dipeptidyl peptidase IV.
  • Fluoropyrrolidine contaning N--ethylurea pyrazole derivatives as potential and selective inhibitors for Trypanosoma brucei and Trypanosoma cruzi parasitic causative agents.
  • Urea derivatives of (S)-2-(3,4-difluorophenyl)-5-(3-fluoro-N-pyrrolidylamido)benzothiazole as potent antitrypanosomal agents.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - 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)

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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Urea derivatives of 2-aryl-benzothiazol-5-amines: a new class of potential drugs for human African trypanosomiasis
Patrick DA, et al.
Journal of Medicinal Chemistry, 60(3), 957-971 (2017)
Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors
Caldwell CG, et al.
Bioorganic & Medicinal Chemistry Letters, 14(5), 1265-1268 (2004)
Discovery of Potent N-Ethylurea Pyrazole Derivatives as Dual Inhibitors of Trypanosoma brucei and Trypanosoma cruzi
Varghese S, et al.
ACS Medicinal Chemistry Letters (2019)
Charles G Caldwell et al.
Bioorganic & medicinal chemistry letters, 14(5), 1265-1268 (2004-02-26)
Amides derived from fluorinated pyrrolidines and 4-substituted cyclohexylglycine analogues have been prepared and evaluated as inhibitors of dipeptidyl dipeptidase IV (DP-IV). Analogues which incorporated (S)-3-fluoropyrrolidine showed good selectivity for DP-IV over quiescent cell proline dipeptidase (QPP). Compound 48 had good

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