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274984 Sigma-Aldrich

18-Crown-6

≥99.0%

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

  • CAS Number 17455-13-9

  • Empirical Formula (Hill Notation) C12H24O6

  • Molecular Weight 264.32

  •  Beilstein/REAXYS Number 1619616

  •  EC Number 241-473-5

  •  MDL number MFCD00005113

  •  PubChem Substance ID 24856618

  •  NACRES NA.22

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Properties

Related Categories Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers, Synthetic Reagents
Quality Level   200
assay   ≥99.0%
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 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.

Packaging

1 g in glass bottle

Other Notes

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

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
MP4500000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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901591 18-Crown-6 solution, 1.0 M in THF

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