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B21503 3-Quinuclidinol, 98+%

CAS Number
1619-34-7
Synonyms
1-Azabicyclo[2.2.2]octan-3-ol
3-Hydroxyquinuclidine

Stock No. Size Price ($) Quantity Availability
B21503-06 5g 33.10
B21503-14 25g 99.30
B21503-22 100g 329.00
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3-Quinuclidinol, 98+%

MDL
MFCD00151326
EINECS
216-578-4

Chemical Properties

Formula
C7H13NO
Formula Weight
127.19
Melting point
217-224°
Storage & Sensitivity
Air Sensitive. Store under Argon. Ambient temperatures.
Solubility
Soluble in water.

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.

Notes

Incompatible with oxidizing agents.

Literature 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H500

Causes severe skin burns and eye damage. May form combustible dust concentrations in air

Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,8082
Beilstein
104327
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2933.39
TSCA
Yes
RTECS
VD6191700

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