274984

18-Crown-6

≥99.0%

• Synonym(s): 1,4,7,10,13,16-Hexaoxacyclooctadecane
• Empirical Formula (Hill Notation): C₁₂H₂₄O₆
• CAS Number: 17455-13-9
• Molecular Weight: 264.32
• Beilstein/REAXYS Number: 1619616
• EC Number: 241-473-5
• MDL number: MFCD00005113
• UNSPSC Code: 12352005
• PubChem Substance ID: 24856618
• NACRES: NA.22

Properties

• assay: ≥99.0%
• form: solid
• mp: 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
• InChI key: XEZNGIUYQVAUSS-UHFFFAOYSA-N

Description

General description

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.

Application

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.

Can be useful as phase-transfer catalysts.

Other Notes

Macrocyclic polyethers with repeating (-CH₂CH₂O) units. The compounds are ionophoric (form stable complexes with cations).

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves