274984
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:
Molecular Weight:
264.32
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
241-473-5
Beilstein/REAXYS Number:
1619616
MDL number:
Assay:
≥99.0%
Form:
solid
Quality Level
assay
≥99.0%
form
solid
reaction suitability
core: crown ether
greener alternative product characteristics
Catalysis
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sustainability
Greener Alternative Product
mp
42-45 °C (lit.)
functional group
ether
greener alternative category
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
General description
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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.
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
Can be useful as phase-transfer catalysts.
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.
Other Notes
Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations).
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signalword
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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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)
18?Crown?6.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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)