186651

18-Crown-6

99%

• Synonym(s): 1,4,7,10,13,16-Hexaoxacyclooctadecane
• 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: 24851233
• NACRES: NA.22

Properties

• 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
• 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

Description

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.

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

Phase-transfer catalyst used in a chemoselective reduction of fused tetrazoles with NaBH₄ and potassium hydroxide.

Can be useful as phase-transfer catalysts.

Other Notes

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• 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