Lot numbers can be found on the outside label of a product:
Ethyl quinuclidine-4-carboxylate
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CAS No. 22766-68-3
- Cat. No. CS-M1578
- Purity≥98%
- MDL No.MFCD19686937
*For research and further manufacturing use only, not for direct human use.
Structure of 22766-68-3
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General Information
- CAS No. 22766-68-3
- Cat. No. CS-M1578
- Purity ≥98%
- MDL No. MFCD19686937
- Storage RT, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₁₇NO₂
- Molecular Weight 183.25
- Synonym(s) None
- SMILES O=C(OCC)C12CCN(CC2)CC1
Description
Ethyl quinuclidine-4-carboxylate is a sterically hindered, bench-stable nitrogen heterocycle featuring a quinuclidine core with an ester-functionalized carboxylate group. This configuration enables efficient incorporation into asymmetric synthesis and catalytic systems, where the rigid framework enhances stereocontrol. The ethyl ester moiety supports downstream transformations such as hydrolysis or amidation without compromising stability.
Application
Ethyl quinuclidine-4-carboxylate serves as a versatile chiral building block in synthetic organic chemistry, leveraging the rigid bicyclic quinuclidine scaffold for stereocontrol. The ester group enables straightforward functionalization via hydrolysis or reduction, while the tertiary amine functions as a robust base and ligand in transition metal catalysis. Its bench stability, clean reactivity profile, and compatibility with diverse transformations make it a reliable component in medicinal chemistry and asymmetric synthesis workflows.
Synthesis
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Route1
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In-stock
869112-14-1 - ~94%
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In-stock
22766-68-3
References
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Laine, Dramane I.; McCleland, Brent; Thomas, Sonia; Neipp, Christopher; Underwood, Brian; Dufour, Jeremy; Widdowson, Katherine L.; Palovich, Michael R.; Blaney, Frank E.; Foley, James J.; Webb, Edward F.; Luttmann, Mark A.; Burman, Miriam; Belmonte, Kristen; Salmon, Michael Journal of Medicinal Chemistry, 2009 , vol. 52, # 8 p. 2493 - 2505
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Route2
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1276088-72-2 - ~%
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In-stock
22766-68-3
References
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GLAXO GROUP LIMITED; CARANGIO, Antonella; CHEUNG, Izabel; D'SOUZA, Erin Carmen Frances; LEAHY, John Henry; STRACHAN, John Bryce Patent: WO2011/29896 A1, 2011 ; Location in patent: Page/Page column 19 ;
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Route3
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In-stock
142851-03-4 - ~%
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In-stock
22766-68-3
References
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GLAXO GROUP LIMITED; CARANGIO, Antonella; CHEUNG, Izabel; D'SOUZA, Erin Carmen Frances; LEAHY, John Henry; STRACHAN, John Bryce Patent: WO2011/29896 A1, 2011 ;
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 29.54
- LogP 1.0354
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 2
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Key Words
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