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274984

Sigma-Aldrich

18-Crown-6

≥99.0%

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Synonym(s):
1,4,7,10,13,16-Hexaoxacyclooctadecane
Empirical Formula (Hill Notation):
C12H24O6
CAS Number:
Molecular Weight:
264.32
Beilstein:
1619616
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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1 of 4

This Item
186651188832158402
18-Crown-6 ≥99.0%

Sigma-Aldrich

274984

18-Crown-6

18-Crown-6 99%

Sigma-Aldrich

186651

18-Crown-6

15-Crown-5 98%

Sigma-Aldrich

188832

15-Crown-5

form

solid

form

solid

form

liquid

form

solid

mp

42-45 °C (lit.)

mp

42-45 °C (lit.)

mp

-

mp

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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).

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Pictograms

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Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

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Principles and synthetic applications in crown ether chemistry
Gokel, George W and Durst, H Dupont
Synthesis, 1976(03), 168-184 (1976)
Improved synthesis and efficient chemoselective reduction of fused tetrazoles under phase-transfer conditions
Desai ND and Shah RD
Synthesis, 2006(19), 3275-3279 (2006)
18?Crown?6.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
18?Crown?6.
Organic Syntheses (2003)
An ab initio investigation of the structure and alkali metal cation selectivity of 18-crown-6
Glendening, et al.
Journal of the American Chemical Society, 116, 10657-10669 (1994)

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