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15-Crown-5

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  • 2026-02-05
  • CAS:33100-27-5
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15-Crown-5 Basic information
use Introduction
Product Name:15-Crown-5
Synonyms:1,4,10,13-Pentaoxacyclopentadecane;15-Crown-5,1,4,7,10,13-Pentaoxa-cyclo-pentadecane;Crownethers;Ethyleneoxidecyclicpentamer;15-Crown-5 Vetec(TM) reagent grade, 98%;1,4,7,1,13-Pentaoxacyclopentadecane;15-Crown-5 solution;LABOTEST-BB LT00440921
CAS:33100-27-5
MF:C10H20O5
MW:220.26
EINECS:251-379-6
Product Categories:Pyridines;catalyst;crown ether;Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry;bc0001;33100-27-5
Mol File:33100-27-5.mol
15-Crown-5 Structure
15-Crown-5 Chemical Properties
Melting point -20°C(lit.)
Boiling point 93-96 °C/0.05 mmHg (lit.)
density 1.113 g/mL at 20 °C (lit.)
vapor pressure 0.5-0.82Pa at 20-25℃
refractive index n20/D 1.465(lit.)
Fp >230 °F
storage temp. room temp
solubility Miscible with organic solvents.
form Liquid
color Clear colorless to light yellow
Specific Gravity1.109
Water Solubility MISCIBLE
Sensitive Hygroscopic
BRN 1618144
Stability:Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air.
InChI1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
InChIKeyVFTFKUDGYRBSAL-UHFFFAOYSA-N
SMILESO1CCOCCOCCOCCOCC1
LogP-0.9 at 20℃ and pH7.7
Surface tension68.5mN/m at 1g/L and 20℃
CAS DataBase Reference33100-27-5(CAS DataBase Reference)
NIST Chemistry Reference15-Crown-5(33100-27-5)
EPA Substance Registry System1,4,7,10,13-Pentaoxacyclopentadecane (33100-27-5)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/38-36-20/22-36/37/38-20/21/22
Safety Statements 26-39-36
RIDADR 2810
WGK Germany 3
RTECS SB0200000
10-21
Hazard Note Irritant
TSCA TSCA listed
HazardClass 6.1(b)
PackingGroup III
HS Code 29329995
Storage Class10 - Combustible liquids
Hazard ClassificationsAcute Tox. 4 Oral
ToxicityLD50 orl-rat: 1410 mg/kg DCTODJ 1,339,78
MSDS Information
ProviderLanguage
15-Crown-5 English
ACROS English
SigmaAldrich English
ALFA English
15-Crown-5 Usage And Synthesis
use

15-crown-5 has also been used to isolate salts of oxonium ions. For example, from a solution of tetrachloroauric acid, the oxonium ion [H7O3]+ has been isolated as the salt [(H7O3)(15-crown-5)2][AuCl4].

Introduction

The single nitrogen-containing derivative of 15-crown-5 is called aza-15-crown-5; the prefix “mono” is unnecessary. When two or more nitrogen atoms are present, the standard prefixes di-, tri-, etc. are applied. The term “monoazacrowns” is used here to designate the class of macrocycles containing a single nitrogen in combination with oxygen atoms as the macrocyclic donor array.

Chemical Propertiescolourless liquid
Uses15-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.
DefinitionChEBI: A saturated organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether.
General Description15-Crown-5 is a crown ether generally used as a ligand in coordination chemistry because of its strong chelating property with certain alkali cations to form complexes. Some derivatives of 15-crown-5 are used as sensors and probes in different physical-chemical processes, phase-transfer reactions, and selective capture of ions for separation and transport.
Safety ProfileModerately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye . When heated to decomposition it emits acrid smoke and irritating fumes
Purification MethodsDry it over 3A molecular sieves and distil it in a high vacuum. [Beilstein 19/12 V 252.]
Tag:15-Crown-5(33100-27-5) Related Product Information
12-Crown-4 CYCLOHEXANO-15-CROWN-5 4-T-BUTYLCYCLOHEXANO-15-CROWN-5,4-TERT-BUTYLCYCLOHEXANO-15-CROWN-5 Hydroxy-15-crown-5,2-(HYDROXYMETHYL)-15-CROWN 5-ETHER,2-HYDROXYMETHYL-15-CROWN-5 4'-FORMYLBENZO-15-CROWN-5,4'-FORMYLBENZO-15-CROWN 5-ETHER 4'-BROMOBENZO-15-CROWN-5,4'-BROMOBENZO-15-CROWN 5-ETHER,4-BROMOBENZO-15-CROWN-5 4'-NITROBENZO-15-CROWN-5,4-NITROBENZO-15-CROWN-5,4'-NITROBENZO-15-CROWN 5-ETHER DIBENZO-15-CROWN-5 4'-CARBOXYBENZO-15-CROWN-5,4-CARBOXYBENZO-15-CROWN-5,4'-CARBOXYBENZO-15-CROWN 5-ETHER 4-AMINOBENZO-15-CROWN-5 HYDROCHLORIDE,4'-AMINOBENZO-15-CROWN-5 HYDROCHLORIDE 4'-AMINOBENZO-15-CROWN 5-ETHER,4'-AMINOBENZO-15-CROWN-5 1-AZA-15-CROWN-5,1-AZA-15-CROWN 5-ETHER 4-TERT-BUTYLBENZO-15-CROWN-5,4-T-BUTYLBENZO-15-CROWN-5,tert-Butylbezno-15-crown-5 Benzo-15-crown-5 4,10-DIAZA-15-CROWN 5-ETHER,1,7-DIAZA-15-CROWN-5 4'-(2,4-DINITRO-6-TRIFLUOROMETHYLPHENYL)-AMINOBENZO-15-CROWN-5,4'-(2'',4''-DINITRO-6''-TRIFLUOROMETHYLPHENYL)-AMINOBENZO-15-CROWN-5 Dibenzodiaza-15-crown-4 2,3-NAPHTHO-15-CROWN-5

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