274984
18-Crown-6
≥99.0%
Sinónimos:
1,4,7,10,13,16-Hexaoxacyclooctadecane
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Acerca de este artículo
Fórmula empírica (notación de Hill):
C12H24O6
Número CAS:
Peso molecular:
264.32
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
241-473-5
Beilstein/REAXYS Number:
1619616
MDL number:
Assay:
≥99.0%
Form:
solid
Servicio técnico
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Permítanos ayudarleQuality Segment
assay
≥99.0%
form
solid
reaction suitability
core: crown ether
greener alternative product characteristics
Catalysis
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Greener Alternative Product
mp
42-45 °C (lit.)
functional group
ether
greener alternative category
SMILES string
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
InChI key
XEZNGIUYQVAUSS-UHFFFAOYSA-N
General description
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.
18-Crown-6 is a macrocyclic polyether used to synthesize ionic liquid based crown-ether coordination compounds.
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.
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.
Application
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.
- Allylation of aldehydes to corresponding homoallylic alcohols using potassium allyltrifluoroborate.
- Preparation of N-propargylpyrrole by the reaction of pyrrole with potassium hydroxide.
- Polymerization of methacrylic esters and hindered alkyl acrylates.
- Chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide.
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.
Other Notes
Poliéteres macrocíclicos con repetición de unidades (-CH2CH2O). Los compuestos son ionofóricos (forman compuestos estables con cationes).
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Contenido relacionado
Gokel, G.W.
Crown Ethers and Cryptands (1991)
18-Crown-6
Liotta, Charles, L and Berkner, Joachim
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Improved synthesis and efficient chemoselective reduction of fused tetrazoles under phase-transfer conditions
Desai ND and Shah RD
Synthesis, 2006(19), 3275-3279 (2006)