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274984

Sigma-Aldrich

18-Crown-6

≥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:
17455-13-9
Molecular Weight:
264.32
Beilstein:
1619616
EC Number:
241-473-5
MDL number:
MFCD00005113
UNSPSC Code:
12352005
PubChem Substance ID:
24856618
NACRES:
NA.22

Quality Level

200

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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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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Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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)
Gokel, G.W.
Crown Ethers and Cryptands (1991)
18-Crown-6
Liotta, Charles, L and Berkner, Joachim
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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