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For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf
274984
18-Crown-6
≥99.0%
Synonym(s):
1,4,7,10,13,16-Hexaoxacyclooctadecane
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About This Item
Recommended Products
Quality Level
Assay
≥99.0%
form
solid
mp
42-45 °C (lit.)
functional group
ether
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 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.[3][4]
Application
- N-alkylation of heterocyclic compounds in the presence of tert-butoxide base.[5]
- Allylation of aldehydes to corresponding homoallylic alcohols using potassium allyltrifluoroborate.[6]
- Preparation of N-propargylpyrrole by the reaction of pyrrole with potassium hydroxide.[4]
- Polymerization of methacrylic esters and hindered alkyl acrylates.[4]
- Chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide.[7]
Other Notes
related product
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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