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197602

Sigma-Aldrich

Quinuclidine

97%

Sinonimo/i:

1-Azabicyclo[2.2.2]octane, ABCO

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About This Item

Formula empirica (notazione di Hill):
C7H13N
Numero CAS:
100-76-5
Peso molecolare:
111.18
Beilstein:
103111
Numero CE:
202-887-1
Numero MDL:
MFCD00006690
Codice UNSPSC:
12352100
ID PubChem:
24851837
NACRES:
NA.22
Stato:
solid
Saggio:
97%
Prezzi e disponibilità al momento non sono disponibili

Tensione di vapore

1.5 mmHg ( 20 °C)

Livello qualitativo

100

Saggio

97%

Stato

solid

Punto di fusione

157-160 °C (lit.)

Solubilità

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

Stringa SMILE

C1CN2CCC1CC2

InChI

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

Informazioni sul gene

rat ... Chrm1(25229)

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Categorie correlate

Descrizione generale

Quinuclidine is a bicyclic tertiary amine with a bridgehead nitrogen atom structure, often used in the synthesis of iodonium complexes and as a hydrogen-atom-transfer (HAT) catalyst in photo induced reactions. [1]

Applicazioni

Quinuclidine can be used as a catalyst:
  • In the Baylis-Hillman reaction of aldehydes with methyl acrylate[2].
  • For the epimerization of α-methylglucose to α-methylallose[3].
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[4].

Pittogrammi

Skull and crossbonesCorrosion
GHS06,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H301,H310,H315,H318

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
SHBQ8325
SHBP7746
SHBN0349
SHBJ9432
SHBH6046

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Sigma-Aldrich

CDS019247

2-Azabicyclo[2.2.1]heptane

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
Yong Wang et al.
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
H P Kertscher et al.
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
Journal of the American Chemical Society, 115, 7047-7047 (1993)
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
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