CAS 33100-27-5 15-Crown 5-Ether - Materials / Alfa Chemistry

NAVIGATION

15-Crown 5-Ether

PRICE INQUIRY

Catalog Number

ACM33100275-1

CAS Number

33100-27-5

Product Name

15-Crown 5-Ether

Category

Macrocycles; Supramolecular Host Materials

IUPAC Name

1,4,7,10,13-pentaoxacyclopentadecane

Molecular Weight

220.26g/mol

Molecular Formula

C10H20O5

Canonical SMILES

C1COCCOCCOCCOCCO1

InChI

InChI=1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2

InChI Key

VFTFKUDGYRBSAL-UHFFFAOYSA-N

Application

15-Crown-5-Ether is a versatile compound used primarily as an efficient phase transfer catalyst and complexing agent. This colorless liquid plays a crucial role in isolating oxonium ion (H7O3)+ salts, particularly from solutions of tetrachloroauric acid. It facilitates the esterification reaction by catalyzing the O-alkylation of sodium carboxylate salts in the penicillin and cephalosporin families, all without requiring the use of acid. Additionally, 15-Crown-5-Ether aids in the Williamson synthesis of ethers, especially with hindered alcohols and sodium hydride, and enhances reduction reactions with lithium aluminum hydride in hydrocarbon solvents. It is also instrumental in the Horner-Wadsworth-Emmons reaction, allowing for the synthesis of stilbenes from aldehydes. The compound is a saturated organic heteromonocycle, based on cyclopentadecane, where specific carbon atoms are replaced by oxygen atoms to create its crown ether structure.

Complexity

86.2

Covalently-Bonded Unit Count

EC Number

251-379-6

Exact Mass

220.131074g/mol

Formal Charge

Heavy Atom Count

Log P

-0.48 (LogP)

MeSH Entry Terms