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1-Azabicyclo[2.2.2]octane-3-carboxylicacid, ethyl ester

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Name

1-Azabicyclo[2.2.2]octane-3-carboxylicacid, ethyl ester

EINECS 604-604-1
CAS No. 6238-33-1 Density 1.09 g/cm3
PSA 29.54000 LogP 0.82920
Solubility N/A Melting Point N/A
Formula C10H17NO2 Boiling Point 240.8 °C at 760 mmHg
Molecular Weight 183.25 Flash Point 89.6 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 6238-33-1 (ETHYL 3-QUINUCLIDINECARBOXYLATE) Hazard Symbols N/A
Synonyms

3-Quinuclidinecarboxylicacid, ethyl ester (7CI,8CI);3-Carbethoxyquinuclidine;Ethyl 3-quinuclidinecarboxylate;

 

1-Azabicyclo[2.2.2]octane-3-carboxylicacid, ethyl ester Synthetic route

6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

75208-40-1

quinuclidine-3-carboxylic acid

Conditions
ConditionsYield
With water for 3h; Heating;100%
With hydrogenchloride for 5h; Heating;
With hydrogenchloride Heating;
6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

5176-22-7

3-hydroxymethyl-1-azabicyclo[2.2.2]octane

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;91%
6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

6238-34-2

1-azabicyclo<2.2.2>octane-3-carboxylic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;80%
188290-36-0

thiophene

108-86-1

bromobenzene

6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

591-51-5

phenyllithium

57734-76-6

di(2-thienyl)(3-quinuclidyl)carbinol hydrochloride

Conditions
ConditionsYield
Stage #1: bromobenzene With lithium In diethyl ether for 1h; Metallation; Heating;
Stage #2: thiophene; phenyllithium at 25℃; for 0.75h; Addition;
Stage #3: 3-quinuclidinecarboxylic acid ethyl ester In diethyl ether at -10 - -5℃; for 0.5h; Condensation;
67.4%
188290-36-0

thiophene

108-86-1

bromobenzene

6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

57734-76-6

di(2-thienyl)(3-quinuclidyl)carbinol hydrochloride

Conditions
ConditionsYield
Stage #1: bromobenzene With lithium In diethyl ether for 1h; Metallation; Heating;
Stage #2: thiophene In diethyl ether at 20℃; for 1.5h; Metallation;
Stage #3: 3-quinuclidinecarboxylic acid ethyl ester With hydrogenchloride In diethyl ether; water at -10 - 20℃; for 1.5h; Addition;
67%
126145-44-6

N-Hydroxy-2-(2-oxo-pyrrolidin-1-yl)-acetamidine

6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

1-((5-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,4-oxadiazol-3-yl)methyl)pyrrolidin-2-one

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Schlenk technique; Molecular sieve; Reflux;47%
1003-09-4

2-bromothiophene

6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

60697-86-1

(3-quinuclidyl)(2-thienyl)ketone

Conditions
ConditionsYield
(i) Mg, Et2O, (ii) /BRN= 473684/; Multistep reaction;
1003-09-4

2-bromothiophene

6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

57734-75-5

(3-Quinuclidyl) di(2-thienyl) carbinol

Conditions
ConditionsYield
(i) Mg, Et2O, (ii) /BRN= 473684/; Multistep reaction;
6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

5713-61-1

thiophen-2-yl magnesium bromide

60697-86-1

(3-quinuclidyl)(2-thienyl)ketone

Conditions
ConditionsYield
In diethyl ether
6238-33-1

3-quinuclidinecarboxylic acid ethyl ester

5713-61-1

thiophen-2-yl magnesium bromide

57734-75-5

(3-Quinuclidyl) di(2-thienyl) carbinol

Conditions
ConditionsYield
In diethyl ether

1-Azabicyclo[2.2.2]octane-3-carboxylicacid, ethyl ester Specification

The 1-Azabicyclo[2. 2. 2]octane-3-carboxylicacid, ethyl ester, with the CAS registry number of 6238-33-1, is also known as 3-Carbethoxyquinuclidine. It belongs to the product category of Quinuclidine Derivatives. This chemical's molecular formula is C10H17NO2 and molecular weight is 183.25. What's more, its systematic name is called Ethyl 1-azabicyclo[2. 2. 2]octane-3-carboxylate.

Physical properties about 1-Azabicyclo[2. 2. 2]octane-3-carboxylicacid, ethyl ester are: (1)ACD/LogP: 1.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.65; (4)ACD/LogD (pH 7.4): -0.57; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1.49; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.54 Å2; (13)Index of Refraction: 1.507; (14)Molar Refractivity: 49.95 cm3; (15)Molar Volume: 167.6 cm3; (16)Polarizability: 19.8×10-24 cm3; (17)Surface Tension: 39 dyne/cm; (18)Density: 1.09 g/cm3; (19)Flash Point: 89.6 °C; (20)Enthalpy of Vaporization: 47.77 kJ/mol; (21)Boiling Point: 240.8 °C at 760 mmHg; (22)Vapour Pressure: 0.0373 mmHg at 25 °C.

Uses: it is used to produce other chemicals. For example, it is used to produce Quiniuclidin-3-yl-methanol. The reaction needs reagent LiAlH4 and solvent Diethyl ether. Other condition of this reaction is reaction time of 2 hours at heating. The yield is about 91 %.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OCC)C1CN2CCC1CC2
(2) InChI: InChI=1/C10H17NO2/c1-2-13-10(12)9-7-11-5-3-8(9)4-6-11/h8-9H,2-7H2,1H3
(3) InChIKey: ZNYZKXCVJJQSEU-UHFFFAOYAG

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