ChemicalBook > CAS DataBase List > 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester

1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester

Product Name
1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester
CAS No.
22766-68-3
Chemical Name
1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester
Synonyms
UMECLIDINIUM INT;Quinuclidine-4-carboxylic acid ethyl ester;ethyl-1-azabicyclo[2.2.2]octane-4-carboxylate;azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester;1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester;Diphenyl(quinuclidin-4-yl)methanolEthyl quinuclidine-4-carboxylate
CBNumber
CB62240411
Molecular Formula
C10H17NO2
Formula Weight
183.25
MOL File
22766-68-3.mol
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1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester Property

Boiling point:
233.4±40.0 °C(Predicted)
Density 
1.09±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
pka
9.44±0.12(Predicted)
Appearance
Colorless to light yellow Liquid
InChI
InChI=1S/C10H17NO2/c1-2-13-9(12)10-3-6-11(7-4-10)8-5-10/h2-8H2,1H3
InChIKey
MMXIVBVOFFBDEB-UHFFFAOYSA-N
SMILES
N12CCC(C(OCC)=O)(CC1)CC2
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Safety

HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

TRC
Product number
E925945
Product name
Ethyl4-Quinuclidinecarboxylate
Packaging
1g
Price
$95
Updated
2021/12/16
AK Scientific
Product number
3657AH
Product name
Ethylquinuclidine-4-carboxylate
Packaging
1g
Price
$140
Updated
2021/12/16
ChemScene
Product number
CS-M1578
Product name
Ethylquinuclidine-4-carboxylate
Purity
99.25%
Packaging
5g
Price
$205
Updated
2021/12/16
ChemScene
Product number
CS-M1578
Product name
Ethylquinuclidine-4-carboxylate
Purity
99.25%
Packaging
1g
Price
$70
Updated
2021/12/16
ChemScene
Product number
CS-M1578
Product name
Ethylquinuclidine-4-carboxylate
Purity
99.25%
Packaging
10g
Price
$357
Updated
2021/12/16
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1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester Chemical Properties,Usage,Production

Uses

Ethyl 4-Quinuclidinecarboxylate is a reactant used in the synthesis of azoniabicyclooctanes as muscarinic acetylcholine receptor antagonists.

Synthesis

869112-14-1

22766-68-3

General procedure: ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (II) (5.0 g, 22.76 mmol) was dissolved in tetrahydrofuran (THF, 147.0 mL) under nitrogen protection and the solution was cooled to -50 °C. At -50 °C, LDA (2.0 M in heptane/THF/ethylbenzene, 17.0 mL, 34.0 mmol) was added slowly over 25 min. The reaction mixture was gradually warmed to room temperature over 16 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous K2CO3 solution (122.0 mL) and extracted with ether (3 x 120.0 mL). The organic layers were combined, dried with MgSO4, filtered and concentrated under reduced pressure. The resulting orange liquid was co-evaporated three times with dichloromethane to remove excess ethylbenzene, resulting in an orange oily product (4.15 g, 99.4% yield). The product was ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (III) with the following 1H-NMR (300 MHz, CDCl3) data: δ4.10 (t, J=5.23 Hz, 2H), 2.90-2.85 (m, 6H), 1.71-1.66 (m, 6H), 1.22 (t, J=4.0 Hz, 3H).

References

[1] Patent: WO2018/87561, 2018, A1. Location in patent: Page/Page column 13
[2] Patent: US2007/185155, 2007, A1. Location in patent: Page/Page column 9
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2493 - 2505
[4] Patent: WO2005/112644, 2005, A2. Location in patent: Page/Page column 13
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 4, p. 1152 - 1157

1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Product
Ethyl quinuclidine-4-carboxylate 22766-68-3
Price
US $2.00-6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2025-08-05
Career Henan Chemical Co
Product
1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester 22766-68-3
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2020-02-13

22766-68-3, 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl esterRelated Search:

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  • 1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester
  • Quinuclidine-4-carboxylic acid ethyl ester
  • ethyl-1-azabicyclo[2.2.2]octane-4-carboxylate
  • Diphenyl(quinuclidin-4-yl)methanolEthyl quinuclidine-4-carboxylate
  • azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester
  • UMECLIDINIUM INT
  • 22766-68-3