15-Crown-5

• Catalog No.: A12265
• CAS Number: 33100-27-5
• M. F.: C10H20O5
• M. W.: 220.2628
• Purity: 98%

SYNONYMS

• Title: 15-冠-5醚
• IUPAC name: 1,4,7,10,13-pentaoxacyclopentadecane
• IUPAC Traditional name: 15-crown-5 ether
• Synonyms: 1,4,7,10,13-Pentaoxacyclopentadecane

DATABASE IDS

• EC Number: 251-379-6
• CAS Number: 33100-27-5
• Beilstein Number: 1618144
• MDL Number: MFCD00005110

PROPERTIES

• Purity: 98%
• Boiling Point: 150-155°C/0.5mm
• Density: 1.110
• Flash Point: >110°C(230°F)
• Refractive Index: 1.4650
• GHS Hazard statements: H301-H315-H319-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Risk Statements: 22-36/37/38
• RTECS: SB0200000
• Safety Statements: 23-26-36/37
• Storage Warning: Hygroscopic
• TSCA Listed: 是

REFERENCES

• Crown ether (see Appendix 2) especially suited to complexing sodium ions. Thus, catalyzes the O-alkylation of the Na salts of carboxylic acids in the penicillin and cephalosporin series, providing a method for esterification without exposure to acid: Synthesis, 52, (1986).
• Greatly facilitates the Williamson synthesis of ethers with hindered alcohols and NaH: Tetrahedron Lett., 38, 4679 (1997). Promotes the cleavage of unsymmetrical ethers by Sodium iodide, A15480, in the opposite sense to BBr₃, i.e. by nucleophilic displacement from the less substituted carbon atom: Tetrahedron Lett., 22, 4239 (1981).
• Greatly increases the reactivity of phosphonate anions generated by reaction with NaH in the Horner-Wadsworth-Emmons reaction. Thus, has been used in a high-yield synthesis of stilbenes from aldehydes and Diethyl benzylphosphonate, A10645: Synthesis, 117 (1981).
• Use in combination with Lithium aluminum hydride, A18116, enables reductions to be carried out in hydrocarbon solvents: J. Chem. Soc., Chem. Commun., 1234 (1985).