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A12265 15-Crown-5, 98%

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

Stock No. Size Price ($) Quantity Availability
A12265-03 1g 15.90
A12265-06 5g 46.80
A12265-14 25g 150.00
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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
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
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 (H7O3)+ 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. J. Phys. Chem. A 2015, 119 (29), 8097-8105.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H319-H332

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled.

Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1618144
Harmonized Tariff Code
2932.99
TSCA
Yes
RTECS
SB0200000

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