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274984

Sigma-Aldrich

18-Crown-6

≥99.0%

Sinónimos:

1,4,7,10,13,16-Hexaoxacyclooctadecane

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About This Item

Fórmula empírica (notación de Hill):
C12H24O6
Número de CAS:
17455-13-9
Peso molecular:
264.32
Beilstein:
1619616
Número CE:
241-473-5
Número MDL:
MFCD00005113
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
24856618
NACRES:
NA.22

MXP 1,847.00

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Ensayo

≥99.0%

Formulario

solid

mp

42-45 °C (lit.)

grupo funcional

ether

cadena SMILES

O1CCOCCOCCOCCOCCOCC1

InChI

1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2

Clave InChI

XEZNGIUYQVAUSS-UHFFFAOYSA-N

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Descripción general

18-Crown-6 is a macrocyclic polyether used to synthesize ionic liquid based crown-ether coordination compounds.[1] [2]

18-Crown-6 is the simplest crown ether that can be prepared by reacting triethylene glycol with triethylene glycol dichloride in the presence of potassium hydroxide as a base. 18-Crown-6 can solubilize metal salts, particularly potassium salts, in nonpolar and dipolar aprotic solvents. Thus, it is widely used as a phase transfer catalyst. It can also be used as a metal complexing agent to prepare a variety of molecular complexes.[3][4]

Aplicación

Puede ser útil como catalizador de transferencia de fase.
18-Crown-6 can be used as a catalyst for:       
  • N-alkylation of heterocyclic compounds in the presence of tert-butoxide base.[5]      
  • Allylation of aldehydes to corresponding homoallylic alcohols using potassium allyltrifluoroborate.[6]     
  •   Preparation of N-propargylpyrrole by the reaction of pyrrole with potassium hydroxide.[4]     
  •   Polymerization of methacrylic esters and hindered alkyl acrylates.[4]       
  • Chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide.[7]

18-Crown-6 can solubilize metal salts, particularly potassium salts, in nonpolar and dipolar aprotic solvents. Thus, it is widely used as a phase transfer catalyst.[8][9] It can also be used as a metal complexing agent to prepare a variety of molecular complexes.[10][11]

Otras notas

Poliéteres macrocíclicos con repetición de unidades (-CH2CH2O). Los compuestos son ionofóricos (forman compuestos estables con cationes).

Producto relacionado

Referencia del producto
Descripción
Precios

901591

18-Crown-6 solution, 1.0 M in THF

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

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

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCJ0689
BCCC0558
BCBT9495
BCBT1050
BCBQ8870V

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Improved synthesis and efficient chemoselective reduction of fused tetrazoles under phase-transfer conditions
Desai ND and Shah RD
Synthesis, 2006(19), 3275-3279 (2006)
Principles and synthetic applications in crown ether chemistry
Gokel, George W and Durst, H Dupont
Synthesis, 1976(03), 168-184 (1976)
Magnetic blocking at 10 K and a dipolar-mediated avalanche in salts of the bis (?8-cyclooctatetraenide) complex [Er (COT) 2]?.
Meihaus K R, et al.
Journal of the American Chemical Society, 135(47), 17952-17957 (2013)
18?Crown?6.
Organic Syntheses (2003)
Completing the series of +2 ions for the lanthanide elements: synthesis of molecular complexes of Pr2+, Gd2+, Tb2+, and Lu2+.
MacDonald M R, et al.
Journal of the American Chemical Society, 135(26), 9857-9868 (2013)
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Questions

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  1. 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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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