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197602

Sigma-Aldrich

Quinuclidine

97%

Sinónimos:

1-Azabicyclo[2.2.2]octane, ABCO

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1 G
$173.000
10 G
$883.000

$173.000

Fecha estimada de envío05 de mayo de 2025

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1 G
$173.000
10 G
$883.000

About This Item

Fórmula empírica (notación de Hill):
C7H13N
Número de CAS:
100-76-5
Peso molecular:
111.18
Beilstein:
103111
Número CE:
202-887-1
Número MDL:
MFCD00006690
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24851837
NACRES:
NA.22

$173.000

Fecha estimada de envío05 de mayo de 2025

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presión de vapor

1.5 mmHg ( 20 °C)

Nivel de calidad

100

Ensayo

97%

Formulario

solid

mp

157-160 °C (lit.)

solubilidad

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

cadena SMILES

C1CN2CCC1CC2

InChI

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

Clave InChI

SBYHFKPVCBCYGV-UHFFFAOYSA-N

Información sobre el gen

rat ... Chrm1(25229)

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Descripción general

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]

Aplicación

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].

Pictogramas

Skull and crossbonesCorrosion
GHS06,GHS05

Palabra de señalización

Danger

Frases de peligro

H301,H310,H315,H318

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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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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
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
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
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
Journal of the American Chemical Society, 115, 7047-7047 (1993)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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