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Merck
CN

186651

18-Crown-6

greener alternative

99%

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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24851233
EC Number:
241-473-5
Beilstein/REAXYS Number:
1619616
MDL number:
MFCD00005113

Key Documents

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Product Name

18-Crown-6, 99%

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%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

42-45 °C (lit.)

functional group

ether

greener alternative category

, Aligned

Quality Level

200

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Application

18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes.
Additive for greener etherification using KF-alumina.
Additive for greener etherification using KF-alumina.

Synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6
Can be useful as phase-transfer catalysts.
Phase-transfer catalyst used in a chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide.

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalysis. Find details here.

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 base.

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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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Certificates of Analysis (COA)

Lot/Batch Number
0000507788
0000507789
0000507789
0000507788
0000453059

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Seul-A Park et al.
Nature communications, 10(1), 2601-2601 (2019-06-15)
Environmental and health concerns force the search for sustainable super engineering plastics (SEPs) that utilise bio-derived cyclic monomers, e.g. isosorbide instead of restricted petrochemicals. However, previously reported bio-derived thermosets or thermoplastics rarely offer thermal/mechanical properties, scalability, or recycling that match
Preparation and purification of 18-crown-6 [1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane].
Gokel GW, et al.
The Journal of Organic Chemistry, 39(16), 2445-2446 (1974)
Synthesis, 3275-3275 (2006)
Muyang Ban et al.
Nature communications, 9(1), 3892-3892 (2018-09-27)
Organometal halide perovskites (OHP) are promising materials for low-cost, high-efficiency light-emitting diodes. In films with a distribution of two-dimensional OHP nanosheets and small three-dimensional nanocrystals, an energy funnel can be realized that concentrates the excitations in highly efficient radiative recombination
Phase-transfer alkylation of heterocycles in the presence of 18-crown-6 and potassium tert-butoxide.
Guida WC and Mathre DJ
The Journal of Organic Chemistry, 45(16), 3172-3176 (1980)
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