274984

18-Krone-6

≥99.0%

• Synonym(e): 1,4,7,10,13,16-Hexaoxacyclooctadecan
• Empirische Formel (Hill-System): C₁₂H₂₄O₆
• CAS-Nummer: 17455-13-9
• Molekulargewicht: 264.32
• Beilstein: 1619616
• EG-Nummer: 241-473-5
• MDL-Nummer: MFCD00005113
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24856618
• NACRES: NA.22

Eigenschaften

• Assay: ≥99.0%
• Form: solid
• mp (Schmelzpunkt): 42-45 °C (lit.)
• 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
• InChIKey: XEZNGIUYQVAUSS-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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.

Kann als Phasentransferkatalysator eingesetzt werden.

Sonstige Hinweise

Makrozyklische Polyether mit sich wiederholenden (-CH₂CH₂O) Einheiten. Die Verbindungen sind ionophor (bilden stabile Komplexe mit Kationen).

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H302
• P-Sätze: P264 - P270 - P301 + P312 - P501
• Gefahreneinstufungen: Acute Tox. 4 Oral
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves