Skip to Content
MilliporeSigma
All Photos(2)

Documents

253340

Sigma-Aldrich

3-Quinuclidinol

99%

Synonym(s):

1-Azabicyclo[2.2.2]octan-3-ol, 3-Hydroxyquinuclidine

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C7H13NO
CAS Number:
1619-34-7
Molecular Weight:
127.18
Beilstein/REAXYS Number:
80122
EC Number:
216-578-4
MDL number:
MFCD00151326
UNSPSC Code:
12352100
PubChem Substance ID:
24855306
NACRES:
NA.22

assay

99%

mp

220-223 °C (lit.)

SMILES string

OC1CN2CC[C@H]1CC2

InChI

1S/C7H13NO/c9-7-5-8-3-1-6(7)2-4-8/h6-7,9H,1-5H2

InChI key

IVLICPVPXWEGCA-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

(R)-3-Quinuclidinol is a valuable compound for the production of various pharmaceuticals.

Application

3-Quinuclidinol has been used:
  • as chiral building block for many antimuscarinic agents
  • in chemoselective α−iodination of various simple and multi-functionalised acrylic esters via Morita-Baylis-Hillman protocol
  • as reagent for cleavage of β-keto and vinylogous β-keto esters
  • as synthon for the preparation of cholinergic receptor ligands and anesthetics
  • as catalyst for condensation of methyl vinyl ketone with aldehydes

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis and local anaesthetic activities of 3-(2-alkoxyphenylcarbamoyloxy)chinuclidinium chlorides.
F Gregán et al.
Die Pharmazie, 48(6), 465-466 (1993-06-01)
V I Cohen et al.
Journal of medicinal chemistry, 34(10), 2989-2993 (1991-10-01)
Seven analogues of 3-quinuclidinyl benzilate (QNB) in which one phenyl ring was replaced by an alkoxyalkyl moiety were synthesized and their affinities for the muscarinic cholinergic receptor determined. An oxygen in the beta-position of the moiety was not well-tolerated. By
Khim.-Farm. Zh., 26, 12-12 (1992)
Tetrahedron Letters, 31, 4509-4509 (1990)
Wen-Xia Zhang et al.
Organic letters, 15(19), 4917-4919 (2013-09-21)
A new keto reductase (ArQR), identified from Agrobacterium radiobacter ECU2556, can efficiently reduce 3-quinuclidinone in excellent enantioselectivity and high space-time yield for the synthesis of (R)-3-quinuclidinol, a chiral building block of many antimuscarinic agents. This is the first time that
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service