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Key Documents

197602

Sigma-Aldrich

Quinuclidine

97%

Synonym(s):

1-Azabicyclo[2.2.2]octane, ABCO

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About This Item

Empirical Formula (Hill Notation):
C7H13N
CAS Number:
Molecular Weight:
111.18
Beilstein:
103111
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

1.5 mmHg ( 20 °C)

Assay

97%

form

solid

mp

157-160 °C (lit.)

solubility

H2O: very slightly soluble
H2O: very soluble
alcohol: miscible
diethyl ether: miscible
organic solvents: very soluble

SMILES string

C1CN2CCC1CC2

InChI

1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2

InChI key

SBYHFKPVCBCYGV-UHFFFAOYSA-N

Gene Information

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Application

Quinuclidine can be used as a catalyst:
  • In the Baylis-Hillman reaction of aldehydes with methyl acrylate.
  • For the epimerization of α-methylglucose to α-methylallose.
It can also be used as a reactant to synthesize 5-[4-[2-(acetyloxy)ethyl]-1-piperidinyl]-2-pyridinecarbonitrile by reacting with 5-bromo-2-pyridinecarbonitrile in the presence of potassium acetate.

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The organocatalyzed addition of several malonates to 1,4-benzoquinones affords benzofuranones bearing a quaternary stereocenter with good enantioselectivity. This reaction is an intramolecular desymmetrization since it proceeds through the formation of an arylated achiral malonate that cyclizes to give the reaction
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The Journal of organic chemistry, 70(6), 2338-2341 (2005-03-12)
[reaction: see text] The ionic liquid-bound quinuclidine catalyzed Baylis-Hillman reactions were investigated. The IL-supported catalyst showed equally good catalytic activity as compared with its nonimmobilized counterpart. The corresponding Baylis-Hillman adducts were obtained in moderate to high yields in all the
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Varinder K Aggarwal et al.
The Journal of organic chemistry, 68(3), 692-700 (2003-02-01)
The reactivity of a variety of quinuclidine-based catalysts in the Baylis-Hillman reaction has been examined, and a straightforward correlation between the basicity of the base and reactivity has been established, without exception. The following order of reactivity was established with

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