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186651 Sigma-Aldrich

18-Crown-6

Green Alternative

99%

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

  • CAS Number 17455-13-9

  • Empirical Formula (Hill Notation) C12H24O6

  • Molecular Weight 264.32

  •  Beilstein/REAXYS Number 1619616

  •  EC Number 241-473-5

  •  MDL number MFCD00005113

  •  PubChem Substance ID 24851233

  •  NACRES NA.22

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Properties

Related Categories 12 Principles Aligned Products, Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers, Greener Alternative Products,
Quality Level   200
assay   99%
greener alternative product characteristics   Catalysis
Learn more about the Principles of Green Chemistry.
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

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.

Packaging

5, 25, 100 g in glass bottle

Other Notes

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

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
MP4500000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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901591 18-Crown-6 solution, 1.0 M in THF

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