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Merck
CN

274984

18-Crown-6

greener alternative

≥99.0%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H24O6
CAS Number:
Molecular Weight:
264.32
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
241-473-5
Beilstein/REAXYS Number:
1619616
MDL number:
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Product Name

18-Crown-6, ≥99.0%

InChI key

XEZNGIUYQVAUSS-UHFFFAOYSA-N

InChI

1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2

SMILES string

O1CCOCCOCCOCCOCCOCC1

assay

≥99.0%

form

solid

Quality Level

greener alternative product characteristics

Catalysis
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sustainability

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mp

42-45 °C (lit.)

functional group

ether

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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.

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.
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Other Notes

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

pictograms

Exclamation mark

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Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
Completing the series of +2 ions for the lanthanide elements: synthesis of molecular complexes of Pr2+, Gd2+, Tb2+, and Lu2+.
MacDonald M R, et al.
Journal of the American Chemical Society, 135(26), 9857-9868 (2013)
18?Crown?6.
Organic Syntheses (2003)
18?Crown?6.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Magnetic blocking at 10 K and a dipolar-mediated avalanche in salts of the bis (?8-cyclooctatetraenide) complex [Er (COT) 2]?.
Meihaus K R, et al.
Journal of the American Chemical Society, 135(47), 17952-17957 (2013)

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