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Sigma-Aldrich

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

97%

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Empirical Formula (Hill Notation):
C4H8FN · HCl
CAS Number:
Molecular Weight:
125.57
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
339822637505694509
form

solid

form

powder

form

solid

form

solid

mp

183-187 °C (lit.)

mp

248-250 °C (lit.)

mp

179-186 °C

mp

133-136 °C

optical activity

[α]20/D +8°, c = 1% in methanol

optical activity

[α]25/D −6.5°, c = 1 in 0.05 M NaOH

optical activity

[α]20/D -8.0°, c = 4 in methanol

optical activity

-

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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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)
Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors
Caldwell CG, et al.
Bioorganic & Medicinal Chemistry Letters, 14(5), 1265-1268 (2004)
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)
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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