Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

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
Pricing and availability is not currently available.

Quality Level

100

Assay

99%

mp

220-223 °C (lit.)

functional group

hydroxyl

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

Related Categories

General description

(R)-3-Quinuclidinol is a valuable compound for the production of various pharmaceuticals[1].

Application

3-Quinuclidinol has been used:
  • as chiral building block for many antimuscarinic agents[2]
  • in chemoselective α−iodination of various simple and multi-functionalised acrylic esters via Morita-Baylis-Hillman protocol[3]
  • as reagent for cleavage of β-keto and vinylogous β-keto esters[4]
  • as synthon for the preparation of cholinergic receptor ligands[5][6] and anesthetics[7]
  • as catalyst for condensation of methyl vinyl ketone with aldehydes[8]

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCX3875
MKCW9340
MKCW3920
MKCV3532
MKCV3493

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

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)
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
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
Tetrahedron Letters, 31, 4509-4509 (1990)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

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