Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

1619-34-7 - 3-Quinuclidinol, 98+% - 1-Azabicyclo[2.2.2]octan-3-ol - 3-Hydroxyquinuclidine - B21503 - Alfa Aesar

B21503 3-Quinuclidinol, 98+%

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

Size Price ($) Quantity Availability
5g 32.60
25g 105.00
100g 322.00
Add to Cart Add to Quote Request View Item

3-Quinuclidinol, 98+%

MDL
MFCD00151326
EINECS
216-578-4

Chemical Properties

Formula
C7H13NO
Formula Weight
127.19
Melting point
217-224°
Sensitivity
Air Sensitive
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-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

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

Other References

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

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware