18-Crown-6
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17455-13-9C1COCCOCCOCCOCCOCCO1XEZNGIUYQVAUSS-UHFFFAOYSA-N18-crown-6 is a crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms. It has a role as a phase-transfer catalyst. It is a saturated organic heteromonocyclic parent and a crown ether.
17455-13-9DTXSID7058626CHEMBL155204CHEBI:32397Other Classes -> Other Organic Compounds
Industrial compound
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Warning
H302 (98.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 314 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Chemical: 1,4,7,10,13,16-Hexaoxacyclooctadecane
Crown ether 18-crown-6: Does not have an individual approval but may be used under an appropriate group standard
If absorbed, can cause electrolyte imbalance affecting the CNS; Signs of intoxication include hyperventilation, tremor, incoordination, and CNS depression; May damage the skin and eyes; LD50 (mouse) by ingestion is 0.7 g/kg; LD50 (rabbit) by skin absorption is 200 mg/kg; [Ullmann] Toxic by ingestion; A skin, eye, and respiratory tract irritant; Oral LD50 (rat) = 525 mg/kg; Dermal LDLo (rat) = 7000 mg/kg; High-dose feeding causes seizures, weight loss, and liver injury in experimental animals; [MSDSonline]
용도18-Crown-6 is used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cation. It is involved in the synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6. It facilitates the solubility of potassium permanganate in benzene, which is used for oxidizing the organic compounds. It is used to accelerate various substitution reactions as well as enhances the power of nucleophiles such as potassium acetate. It is utilized in the alkylation reactions in the presence of potassium carbonate, N-alkylation of glutarimide and succinimide with dimethylcarbonate. The complex formed by its reaction with potassium cyanide acts as a catalyst in the cyanosilylation of aldehydes, ketones and quinines with trimethylsilyl cyanide (TMSCN).
일반 설명18-Crown-6 is the simplest crown ether that can be prepared by reacting triethylene glycol with triethylene glycol dichloride in the presence of potassium hydroxide as a base. 18-Crown-6 can solubilize metal salts, particularly potassium salts, in nonpolar and dipolar aprotic solvents. Thus, it is widely used as a phase transfer catalyst. It can also be used as a metal complexing agent to prepare a variety of molecular complexes.
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18-Crown-6 is a slightly yellow solid, it has a high affinity for the hydronium ion H3O+, as it can fit inside the crown ether. Thus, reaction of 18-crown-6 with strong acids gives the cation [H3O·18-crown-6]+.