3-Quinuclidinol, 98+%, Thermo Scientific Chemicals

Name: 3-Quinuclidinol, 98+%, Thermo Scientific Chemicals
SKU: B21503.22

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Catalog number B21503.22

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100 g

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Chemical Identifiers

CAS1619-34-7

IUPAC Name1-azabicyclo[2.2.2]octan-3-ol

Molecular FormulaC7H13NO

InChI KeyIVLICPVPXWEGCA-UHFFFAOYNA-N

SMILESOC1CN2CCC1CC2

Specifications

Specification Sheet

FormCrystals or powder or crystalline powder or fused/lumpy solid

Assay (Silylated GC)≥98.0%

Identification (FTIR)Conforms

Melting Point (clear melt)219.0-229.0?C

Appearance (Color)White to pale cream

3-Quinuclidinol acts as a chiral building block for various antimuscarinic agents and other active pharmaceutical ingredients. It serves as a catalyst for condensation of methyl vinyl ketone with aldehydes. It is also used as a reagent for cleavage of beta-keto and vinylogous beta-keto esters. Further, it plays an important role as a synthon in the preparation of cholinergic receptor ligands and anesthetics. In addition to this, it is used in chemoselective alfa-iodination of acrylic esters through Morita-Baylis-Hillman reaction.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
3-Quinuclidinol acts as a chiral building block for various antimuscarinic agents and other active pharmaceutical ingredients. It serves as a catalyst for condensation of methyl vinyl ketone with aldehydes. It is also used as a reagent for cleavage of beta-keto and vinylogous beta-keto esters. Further, it plays an important role as a synthon in the preparation of cholinergic receptor ligands and anesthetics. In addition to this, it is used in chemoselective alfa-iodination of acrylic esters through Morita-Baylis-Hillman reaction.

Solubility
Soluble in water.

Notes
Incompatible with oxidizing agents.

RUO – Research Use Only

General References:

Reagent for selective cleavage of ß-keto esters to ketones in high yield: Synth. Commun., 5, 341 (1975). Geminal diesters are converted to monoesters in high yield under similar conditions: J. Org. Chem., 41, 208 (1976).
Superior catalyst for the Baylis-Hillman reaction: the addition of acrylic esters to aldehydes, often very slow (4-7 days) with the usual catalyst 1,4-Diazabicyclo[2.2.2]octane, A14003, is much faster (<1 day) in the presence of quinuclidinol: Synth. Commun., 18, 495 (1988); Tetrahedron Lett., 32, 5611 (1991). For more recent discussion and methodology, see: J. Org. Chem., 67, 510 (2002); 68, 692 (2003). For reviews of the Baylis-Hillman reaction, see: Tetrahedron, 44, 4653 (1988); 52, 8001 (1996). The rate of addition of enones to aldehydes is similarly enhanced: Synth. Commun., 18, 495 (1988); 19, 959 (1989).
Tanokura, M.; Miyakawa, T.; Guan, L.; Hou, F. Structural analysis of enzymes used for bioindustry and bioremediation. Biosci. Biotechnol., Biochem. 2015, 79 (9), 1391-1401.
Kim, H. Y.; Shieh, W. C.; Prashad, M. 3-Quinuclidinol as a nucleophilic catalyst for the cyanation of 2-chloropyrimidines. Tetrahedron Lett. 2014, 55 (36), 5055-5057.