33100-27-5 Usage
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 Properties
colourless liquid
Uses
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.
Definition
ChEBI: 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organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether.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 Description
15-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 Profile
Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye . When heated to decomposition it emits acrid smoke and irritating fumes
Purification Methods
Dry it over 3A molecular sieves and distil it in a high vacuum. [Beilstein 19/12 V 252.]
Check Digit Verification of cas no
The CAS Registry Mumber 33100-27-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,1,0 and 0 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 33100-27:
(7*3)+(6*3)+(5*1)+(4*0)+(3*0)+(2*2)+(1*7)=55
55 % 10 = 5
So 33100-27-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
33100-27-5Relevant articles and documents
LARIAT ETHERS. VI. EVIDENCE FOR INTRAMOLECULAR CHELATION IN SODIUM AND POTASSIUM CATION BINDING BY 15-CROWN-5, CARBON-PIVOT LARIAT ETHERS
Goli, Deepa, M.,Dishong, Dennis, M.,Diamond, Craig, J.,Gokel, George, W.
, p. 5243 - 5246 (1982)
The first compelling evidence for intramolecular sidearm involvement in sodium and potassium cation complexation by carbon-pivot lariat ethers is presented.
15-crown ether -5 method for the preparation of
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Paragraph 0023-0034, (2017/03/21)
The invention relates to a preparation method of 15-crown 5-ether, which comprises the following steps: uniformly stirring triglycol and dioxane in a reaction vessel; adding sodium hydroxide and stirring, heating to 40-60 DEG C; adding a mixed liquor of dichloroethyl ether and dioxane at the temperature lower than 60 DEG C, reacting for 20-24 hours at the temperature of 60-90 DEG C; cooling to room temperature, centrifuging to obtain a filtrate; pumping the filtrate into the reaction vessel and distilling to obtain a distillation substrate; moving the distillation substrate to a stainless steel still, performing vacuum rectification, removing primary fraction to obtain the product. The preparation method has the beneficial effect that comparing with the prior art, the preparation method has the advantages of safe operation, low cost, little three wastes and high yield, and the primary fraction in the reaction can be reutilized.
Thermolysis of the benzene anion radical 18-crown-6 complex
Stevenson, Cheryl D.,Morgan, Grant
, p. 7694 - 7697 (2007/10/03)
The C-O and G-H bonds of 18-crown-6 are activated when 18-crown-6 is complexed with the potassium salt of the benzene anion radical. Evacuated glass bulbs containing the solid anion radical salt of potassium 18-crown-6 benzene anion radical were plunged into a bath at 320 C, resulting in mini-explosions and generating a series of compounds including dioxane, 2-methyl1,3-dioxolane, divinyl ether, hydrogen, methane, and 15-crown-5. Deuterium labeling studies proved that all of these compounds originated from the 18-crown-6. Further, these labeling studies were an aid in discerning the mechanism of the decomposition. Benzene, 1,4-cyclohexadiene, and cyclohexene were also generated. The last two originated from the reaction of the anion radical of benzene with hydrogen.
