Skip to Content
Merck
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:
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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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’.

Already Own This Product?

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

Visit the Document Library

Selective Cleavage of ?-Keto and Vinylogous ?-Keto Esters by 3-Quinuclidinol.
Parish EJ, et al.
Synthetic Communications, 5(5), 341-345 (1975)
Synthesis and local anaesthetic activities of 3-(2-alkoxyphenylcarbamoyloxy)chinuclidinium chlorides.
F Gregán et al.
Die Pharmazie, 48(6), 465-466 (1993-06-01)
Khim.-Farm. Zh., 26, 12-12 (1992)
Tetrahedron Letters, 31, 4509-4509 (1990)
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
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