274984

18-Crown-6

≥99.0%

• Synonyme(s) : 1,4,7,10,13,16-Hexaoxacyclooctadecane
• Formule empirique (notation de Hill) : C₁₂H₂₄O₆
• Numéro CAS: 17455-13-9
• Poids moléculaire : 264.32
• Beilstein: 1619616
• Numéro CE : 241-473-5
• Numéro MDL: MFCD00005113
• Code UNSPSC : 12352005
• ID de substance PubChem : 24856618
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 200
• Essai: ≥99.0%
• Forme: solid
• Pf: 42-45 °C (lit.)
• Groupe fonctionnel: ether
• Chaîne 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
• Clé InChI: XEZNGIUYQVAUSS-UHFFFAOYSA-N

Description

Description générale

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]

Application

Peut être utile en tant que catalyseur de transfert de phase

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]

Autres remarques

Polyéthers macrocyclique avec des unités répétitives (-CH₂CH₂O). Les composés sont des ionophores (forment des complexes stables avec des cations).

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H302
• Conseils de prudence: P264 - P270 - P301 + P312 - P501
• Classification des risques: Acute Tox. 4 Oral
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves