QUINUCLIDINE Chemical Properties

Melting point:

157-160 °C (lit.)

Boiling point:

198.35°C (rough estimate)

Density 

0.8928 (rough estimate)

vapor pressure 

1.5 mm Hg ( 20 °C)

refractive index 

1.4500 (estimate)

storage temp. 

2-8°C, stored under nitrogen

solubility 

H2O: very slightly soluble

pka

10.87±0.33(Predicted)

form 

powder to crystal

color 

White to Light yellow

Water Solubility 

Soluble in alcohol, diethyl ether, water and organic solvents.

Sensitive 

Air Sensitive

Merck 

14,8081

BRN 

103111

InChIKey

SBYHFKPVCBCYGV-UHFFFAOYSA-N

CAS DataBase Reference

100-76-5(CAS DataBase Reference)

EPA Substance Registry System

1-Azabicyclo[2.2.2]octane (100-76-5)

Safety Information

Hazard Codes 

T

Risk Statements 

24/25-38-41

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

CL5594625

F 

2-10

TSCA 

Yes

HS Code 

2933.39.9200

HazardClass 

8

PackingGroup 

III

MSDS

• Language:English Provider:SigmaAldrich

QUINUCLIDINE Usage And Synthesis

Chemical Properties

Quinuclidine is white to light yellow crystalline powder at room temperature and pressure, soluble in most organic solvents, relatively poor solubility in water. The quinuclidine ring molecule contains a lone pair of electrons that can form hydrogen bonds. This gives the quinuclidine ring molecule some hydrogen bond acceptor and donor properties, allowing it to form hydrogen bonding interactions with other molecules. In addition, the compound molecule contains a lone pair of electrons that can accept protons to produce the corresponding ionic form. Under weakly acidic conditions, the quinuclidine ring can be protonated to form positively charged ions.

Uses

Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. It finds application as a ligand, which is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.

Definition

ChEBI: Quinuclidine is a saturated organic heterobicyclic parent and a member of quinuclidines.

Hazard

A poison by ingestion and skin contact. Low toxicity by inhalation. A moderate skin and severe eye irritant.

Purification Methods

Crystallise it from diethyl ether. The hydrochloride has m 364-365o(dec) (from EtOH or n-BuOH), and the picrate has m 225o (from aqueous EtOH). [Beilstein 20 H 144, 20 II 71, 20 III/IV 1966, 20/4 V 335.]

QUINUCLIDINE(100-76-5)Related Product Information

• 3-Aminoquinuclidine dihydrochloride
• A-(6-METHOXY-4-QUINOLYL)-5-VINYL-2-QUINUCLIDINE-METHANOL
• 3-Aminoquinuclidine
• Quinuclidine-4-carboxylic acid ethyl ester
• QUINUCLIDINE
• Cinchonidine
• QUININE FORMATE
• 3-Quinuclidinol hydrochloride
• CINCHONINE SULFATE
• QUINUCLIDINE HYDROCHLORIDE
• A-(6-METHOXY-4-QUINOLYL)-5-VINYL-2-QUINUCLIDINE-METHANOL VALERATE
• 3-Quinuclidinone hydrochloride
• 3-Quinuclidinol
• A-(6-METHOXY-4-QUINOLYL)-5-VINYL-2-QUINUCLIDINE-METHANOL SULFATE
• (S)-3-Aminoquinuclidine dihydrochloride
• 4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE
• (R)-3-Quinuclidinol hydrochloride
• (R)-3-Aminoquinuclidine dihydrochloride