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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:
100-76-5
Molecular Weight:
111.18
Beilstein/REAXYS Number:
103111
EC Number:
202-887-1
MDL number:
MFCD00006690
UNSPSC Code:
12352100
PubChem Substance ID:
24851837
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

rat ... Chrm1(25229)

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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
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Sigma-Aldrich

CDS019247

2-Azabicyclo[2.2.1]heptane

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Knowledge of the relative stabilities of alane (AlH(3)) complexes with electron donors is essential for identifying hydrogen storage materials for vehicular applications that can be regenerated by off-board methods; however, almost no thermodynamic data are available to make this assessment.
Antonio Puglisi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(27), 6941-6945 (2018-03-25)
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
Xueling Mi et al.
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
H P Kertscher et al.
Die Pharmazie, 47(3), 172-174 (1992-03-01)
A series of 11 PAF-analogues, structurally modified in position 1 (alkylcarbamoyloxy), position 2 (n-propyl), and position 3 (polar head group) were synthesized, and the inhibitory potencies on human blood platelets in vitro was evaluated. Investigations of structure-activity relationships revealed, that
Journal of the American Chemical Society, 115, 7047-7047 (1993)
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