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637505

Sigma-Aldrich

(R)-(−)-3-Fluoropyrrolidine hydrochloride

97%

Synonym(s):

(-)-3-Fluoropyrrolidine hydrochloride, (3R)-3-Fluoropyrrolidine hydrochloride, (R)-(-)-3-Fluoropyrrolidine hydrochloride, (R)-3-Fluoropyrrolidine hydrochloride, 3-(R)-Fluoropyrrolidine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C4H9ClFN
CAS Number:
136725-55-8
Molecular Weight:
125.57
MDL number:
MFCD04038717
UNSPSC Code:
12352005
PubChem Substance ID:
24882860
NACRES:
NA.22

Assay

97%

form

solid

optical activity

[α]20/D -8.0°, c = 4 in methanol

mp

179-186 °C

functional group

fluoro

SMILES string

Cl.F[C@@H]1CCNC1

InChI

1S/C4H8FN.ClH/c5-4-1-2-6-3-4;/h4,6H,1-3H2;1H/t4-;/m1./s1

InChI key

LENYOXXELREKGZ-PGMHMLKASA-N

Application

(R)-(−)-3-Fluoropyrrolidine hydrochloride may be used as a substrate in the preparation of:
  • Imidazo[1,2-a]pyrazine derivatives as possible aurora kinase inhibitors.
  • Pyrazolopyrimidine derivatives as possible PDE10A Inhibitors.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ2302
MKBD4021V
MKBD4021
MKBC7697
MKBC1376

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Aurora kinase inhibitors based on the imidazo[1, 2-a] pyrazine core: fluorine and deuterium incorporation improve oral absorption and exposure
Kerekes AD, et al.
Journal of Medicinal Chemistry, 54(1), 201-210 (2011)
Discovery of a pyrazolo [1, 5-a] pyrimidine derivative (MT-3014) as a highly selective PDE10A inhibitor via core structure transformation from the stilbene moiety
Koizumi Y, et al.
Bioorganic & Medicinal Chemistry, 27(15), 3440-3450 (2019)
Scalable Process Design for a PDE10A Inhibitor Consisting of Pyrazolopyrimidine and Quinoxaline as Key Units
Yamagami T, et al.
Organic Process Research & Development, 23(4), 578-587 (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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