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197602

Sigma-Aldrich

Quinuclidine

97%

Sinónimos:

1-Azabicyclo[2.2.2]octane, ABCO

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About This Item

Fórmula empírica (notación de Hill):
C7H13N
Número de CAS:
100-76-5
Peso molecular:
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)

Quality Level

100

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

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Certificados de análisis (COA)

Lot/Batch Number
SHBQ8325
SHBP7746
SHBN0349
SHBJ9432
SHBH6046

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Sigma-Aldrich

CDS019247

2-Azabicyclo[2.2.1]heptane

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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
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)
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Nature, 578(7795), 403-408 (2020-01-16)
Glycans have diverse physiological functions, ranging from energy storage and structural integrity to cell signalling and the regulation of intracellular processes1. Although biomass-derived carbohydrates (such as D-glucose, D-xylose and D-galactose) are extracted on commercial scales, and serve as renewable chemical
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Die Pharmazie, 46(11), 772-774 (1991-11-01)
A series of 13 PAF-analogues with heterocyclane head groups and variation of the P-N-distance on the C-3-position of the backbone were synthesized. The proaggregatory and inhibitory potencies on rabbit and human blood platelets in vitro was evaluated. Investigations of structure-activity
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