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18-Crown-6

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18-Crown-6 Basic information
Product Name:18-Crown-6
Synonyms:18-CROWN-6;CROWN-18-5-ETHER;CROWN ETHER/18-CROWN-6;AKOS BBS-00004361;CROWN ETHER/18-CROWN-6 FOR SYNTHESIS;18 and crown ether;18-Crown-6 >=99.0%;18-Crown-6 99%
CAS:17455-13-9
MF:C12H24O6
MW:264.32
EINECS:241-473-5
Product Categories:crown ether;Miscellaneous Reagents;Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry;API intermediates;catalyst;17455-13-9;bc0001
Mol File:17455-13-9.mol
18-Crown-6 Structure
18-Crown-6 Chemical Properties
Melting point 42-45 °C(lit.)
Boiling point 116°C 0,2mm
density 1,175 g/cm3
refractive index 1.4580 (estimate)
Fp >230 °F
storage temp. Store below +30°C.
solubility Chloroform (Slightly), Methanol (Very Slightly)
form Crystals or Crystalline Mass or Liquid
color White or clear colorless
Water Solubility SOLUBLE
Sensitive Hygroscopic
Merck 14,2602
BRN 1619616
Stability:Stable. Incompatible with strong acids, strong oxidizing agents.
InChIKeyXEZNGIUYQVAUSS-UHFFFAOYSA-N
CAS DataBase Reference17455-13-9(CAS DataBase Reference)
NIST Chemistry Reference1,4,7,10,13,16-Hexaoxacyclooctadecane(17455-13-9)
EPA Substance Registry System1,4,7,10,13,16-Hexaoxacyclooctadecane (17455-13-9)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-36-20/22-20/21/22
Safety Statements 26-36-39
RIDADR 2811
WGK Germany 3
RTECS MP4500000
10
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29329995
ToxicityLD50 orally in Rabbit: 525 mg/kg LD50 dermal Rabbit 3888 mg/kg
MSDS Information
ProviderLanguage
Hexaoxacyclo-octadecane English
SigmaAldrich English
ACROS English
ALFA English
18-Crown-6 Usage And Synthesis
Chemical Propertiesslightly yellow solid
Uses18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes.
UsesA useful phase transfer catalyst.
Uses18-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).
DefinitionChEBI: 18-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 crown ether and a saturated organic heteromonocyclic parent.
Synthesis Reference(s)The Journal of Organic Chemistry, 39, p. 2445, 1974 DOI: 10.1021/jo00930a037
General Description18-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.
Purification MethodsRecrystallise it from acetonitrile and dry it in a vacuum. Purify it also by precipitating the 18-crown-6/nitromethane 1:2 complex with Et2O/nitromethane (10:1 mixture). The complex is decomposed in vacuum whereby 18-crown-6 distils off under the reduced pressure. [Beilstein 19/12 V 601.]
Tag:18-Crown-6(17455-13-9) Related Product Information
Dimethyl ether 2-Butoxyethanol Ethylbenzene 12-Crown-4 Octadecane 4'' 4 (5 )-DI-TERT.BUTYLDICYCLOHEXANO-18-CROWN-6,MIXTUREOFISOMERS (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXYLIC ACID Diethyl ether Dicyclohexano-18-crown-6 1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE-2-METHANOL 4-ACRYLAMIDOBENZO-18-CROWN-6 98% Isobutyl iodide 4',4''(5'')-di-tert-butyldibenzo-18-crown-6, mixed isomers,4,4'-Di-tert-butyldibenzo-18-crown-6 4-AMINOBENZO-18-CROWN-6 PURUM,97% 4-Nitrobenzo-18-crown-6,99% 4-VINYLBENZO-18-CROWN-6 97% 4-(Chloromethyl)styrene homopolymer Dibenzo-18-crown-6,min.98%,1,4,7,14,17,20-HEXAOXA[7.7]ORTHOCYCLOPHANE
DIBENZO-18-CROWN-6,Dibenzo-18-crown-6, 98+%