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33100-27-5 - 15-Crown-5, 98% - 1,4,7,10,13-Pentaoxacyclopentadecane - A12265 - Alfa Aesar

A12265 15-Crown-5, 98%

CAS Number
33100-27-5
Synonyms
1,4,7,10,13-Pentaoxacyclopentadecane

Size Price ($) Quantity Availability
1g 12.00
5g 41.94
25g 140.24
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15-Crown-5, 98%

MDL
MFCD00005110
EINECS
251-379-6

Chemical Properties

Formula
C10H20O5
Formula Weight
220.27
Boiling Point
150-155°/0.5mm
Flash Point
>110°(230°F)
Density
1.110
Refractive Index
1.4650
Sensitivity
Hygroscopic
Solubility
Miscible with organic solvents.

Applications

15-Crown-5 is used as an efficient phase transfer catalyst and as a complexing agent. It is used to isolate oxonium ion (H<sub>7</sub>O<sub>3</sub>)<sup>+</sup> salts especially from a solution of tetrchloroauric acid. It catalyzes the O-alkylation of the sodium salts of carboxylic acids in the penicillin and cephalosporin series, thereby facilitating esterification reaction without usage of acid. It is also used to facilitate the Williamson synthesis of ethers with hindered alcohols and sodium hydride. It is used with lithium aluminum hydride, for performing reduction reactions in hydrocarbon solvents. Further, it is involved in the Horner-Wadsworth-Emmons reaction to prepare stilbenes from aldehydes.

Notes

Hygroscopic. Moisture sensitive. Incompatible with strong oxidizing agents and strong acids.

Literature 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).

Kuo, T. Y.; Tseng, W. H.; Chen, C. H. Force Spectroscopy of Metal-Crown Ether Multivalency: Effect of Local Environments on Energy Landscape and Sensing Kinetics. 2015, 54 (32), 9213-9217.

Inokuchi, Y.; Ebata, T.; Rizzo, T. R. Solvent Effects on the Encapsulation of Divalent Ions by Benzo-18-Crown-6 and Benzo-15-Crown-5. 2015, 119 (29), 8097-8105.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H319-H335-H313

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May be harmful in contact with skin.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1618144
Harmonized Tariff Code
2932.99
TSCA
Yes
RTECS
SB0200000

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