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382981

Sigma-Aldrich

(R)-3-Pyrrolidinol

98%

Synonym(s):

(R)-3-Hydroxypyrrolidine

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About This Item

Empirical Formula (Hill Notation):
C4H9NO
CAS Number:
2799-21-5
Molecular Weight:
87.12
Beilstein/REAXYS Number:
4652606
MDL number:
MFCD00145220
UNSPSC Code:
12352005
PubChem Substance ID:
24863928
NACRES:
NA.22

assay

98%

optical activity

[α]20/D +6.5°, c = 3.5 in methanol

impurities

<2% tetraethylene glycol dimethyl ether

refractive index

n20/D 1.488 (lit.)

bp

215-216 °C (lit.)

density

1.078 g/mL at 20 °C (lit.)

functional group

hydroxyl

SMILES string

O[C@@H]1CCNC1

InChI

1S/C4H9NO/c6-4-1-2-5-3-4/h4-6H,1-3H2/t4-/m1/s1

InChI key

JHHZLHWJQPUNKB-SCSAIBSYSA-N

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Application

Used as a ligand in the enantioselective addition of diethylzinc to aromatic aldehydes leading to optically active secondary alcohols.[1] Also used to prepare-κ-opioid receptor agonists.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCBL8833V
09530AJ
1385017V
1385017
15213BE

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Mehler, T. et al.
Synthetic Communications, 23, 2691-2691 (1993)
A Naylor et al.
Journal of medicinal chemistry, 37(14), 2138-2144 (1994-07-08)
The synthesis of 5-(arylacetyl)-4-[(alkylamino)methyl]furo[3,2-c] pyridines (16-23, 26, 27) and their activities as kappa-opioid receptor agonists are described. kappa-Agonist potency was particularly sensitive to the nature of the basic moiety. In particular, in the rabbit vas deferens (kappa-specific tissue), the 3-pyrrolidinol

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