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197602

Sigma-Aldrich

Chinuclidin

97%

Synonym(e):

1-Azabicyclo[2.2.2]octan

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About This Item

Empirische Formel (Hill-System):
C7H13N
CAS-Nummer:
100-76-5
Molekulargewicht:
111.18
Beilstein:
103111
EG-Nummer:
202-887-1
MDL-Nummer:
MFCD00006690
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24851837
NACRES:
NA.22

Dampfdruck

1.5 mmHg ( 20 °C)

Qualitätsniveau

100

Assay

97%

Form

solid

mp (Schmelzpunkt)

157-160 °C (lit.)

Löslichkeit

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

InChIKey

SBYHFKPVCBCYGV-UHFFFAOYSA-N

Angaben zum Gen

rat ... Chrm1(25229)

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Anwendung

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.

Piktogramme

Skull and crossbonesCorrosion
GHS06,GHS05

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
SHBQ8325
SHBP7746
SHBN0349
SHBJ9432
SHBH6046

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2-Azabicyclo[2.2.1]heptane AldrichCPR

Sigma-Aldrich

CDS019247

2-Azabicyclo[2.2.1]heptane

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
Bryan M Wong et al.
The journal of physical chemistry. C, Nanomaterials and interfaces, 115(15), 7778-7786 (2011-04-21)
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.
Efficient microwave-assisted three-component one-pot preparation of 1-aryl-4-(2-acetoxyethyl) piperazines and 1-aryl-4-(2-acetoxyethyl) piperidines
Gladstone S, et al.
Tetrahedron Letters, 50, 3813-3816 (2009)
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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