18-Crown-6

Base Information

• Chemical Name: 18-Crown-6
• CAS No.: 17455-13-9
• Deprecated CAS: 134316-24-8,168081-58-1,63172-42-9,65154-22-5,66037-87-4,71210-94-1,71211-03-5,71245-01-7,71251-38-2,71251-39-3,71251-42-8,168081-58-1,63172-42-9,65154-22-5,71210-94-1,71211-03-5,71245-01-7,71251-38-2,71251-39-3,71251-42-8
• Molecular Formula: C12H24O6
• Molecular Weight: 264.319
• Hs Code.: 29329995
• European Community (EC) Number: 241-473-5
• NSC Number: 159836
• UNII: 63J177NC5B
• DSSTox Substance ID: DTXSID7058626
• Nikkaji Number: J49.431C
• Wikipedia: 18-Crown-6
• Wikidata: Q3238432
• Metabolomics Workbench ID: 54554
• ChEMBL ID: CHEMBL155204
• Mol file: 17455-13-9.mol

Synonyms:18-Crownether-6;18-Crown-6 ether;Ethylene oxide cyclic hexamer;NSC159836;1,4,7,10,13,16-Hexaoxacyclooctadecane;

Chemical Property of 18-Crown-6

Chemical Property:

• Appearance/Colour: slightly yellow solid
• Vapor Pressure: 4.09E-06mmHg at 25°C
• Melting Point: 42-45 ºC(lit.)
• Refractive Index: 1.404
• Boiling Point: 395.8 ºC at 760 mmHg
• Flash Point: 163.8 ºC
• PSA: 55.38000
• Density: 0.995 g/cm³
• LogP: 0.09960
• Storage Temp.: Store at 0-5°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Methanol (Very Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 264.15728848
• Heavy Atom Count: 18
• Complexity: 108

Purity/Quality:

99.0% min ^*data from raw suppliers

18-Crown-6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-36-20/22-20/21/22
• Safety Statements: 26-36-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1COCCOCCOCCOCCOCCO1
• Description: 1,4,7,10,13,16-Hexaoxacyclooctadecane, commonly known as 18-Crown-6, is a crown ether composed of cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13, and 16 are replaced by oxygen atoms. 1,4,7,10,13,16-Hexaoxacyclooctadecane has a cyclic structure consisting of 18 carbon atoms and 6 oxygen atoms arranged in a crown-like shape. It is categorized as a crown ether and a saturated organic heteromonocyclic compound.
• Uses: 1,4,7,10,13,16-Hexaoxacyclooctadecane is utilized as a phase-transfer catalyst and as a ligand in coordination chemistry. It is also employed in fields such as materials science, luminescence studies, alkali metal ion recognition, and crystal growth morphology control. In coordination chemistry, 1,4,7,10,13,16-Hexaoxacyclooctadecane acts as a chelating ligand, coordinating metal cations and forming stable complexes. In alkali metal ion recognition, it forms complexes with alkali metal ions in aqueous solutions through electrostatic attraction and hydrogen bonding interactions.
• History: Crown ethers, including 1,4,7,10,13,16-Hexaoxacyclooctadecane (18-Crown-6), were discovered by Pedersen and are known for their unique coordination properties with metal cations.
• Production Methods: 1,4,7,10,13,16-Hexaoxacyclooctadecane can be synthesized through chemical reactions involving cyclooctadecane and oxygen-containing compounds.

Technology Process of 18-Crown-6

There total 103 articles about 18-Crown-6 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1,4,7,10,13,16-Hexaoxa-cyclooctadecane-2,9-dione → 18-crown-6 ether (17455-13-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1039/c39820000248

Reference yield: 89.0%

1,4,7,10,13,16-hexaoxacyclooctadecane-2,6-dione (62796-84-3) → 18-crown-6 ether (17455-13-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1039/c39820000248

Reference yield: 83.0%

1,4,7,10,13,16-Hexaoxa-cyclooctadecane-2,12-dione → 18-crown-6 ether (17455-13-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1039/c39820000248

upstream raw materials:

15-crown-5

pentaethylene glycol

1,4,7,10,13,16,10-heptaoxacyclohenicosane

(18-crown-6)potassium

Downstream raw materials:

2-hydroxymethyl-18-crown-6

1,4,7,10,13,16-Hexaoxa-cyclooctadecane; compound with 2,4-dinitro-phenol

n-Decyl-18-crown-6

C₁₂H₂₄O₆*C₄H₈N₂O₃*ClH

Refernces

• 1、 Ochiai, Masahito,Suefuji, Takashi,Miyamoto, Kazunori,Shiro, Motoo. "Effects of complexation with 18-crown-6 on the hypernucleofugality of phenyl-λ3-iodanyl groups. Synthesis of vinyl- λ3-iodane·18-crown-6 complex". . p. 2893 - 2896. Retrieved 2005.
• 2、 Nakatsuji, Yohji,Kameda, Nobuko,Okahara, Mitsuo. "A Facile Synthesis of Hexa- and Octaethylene Glycols". . p. 280 - 281. Retrieved 1987.
• 3、 Bradshaw,J.S. et al.. "-". . p. 134 - 136. Retrieved 1976.
• 4、 Krane, Jostein,Skjetne, Tore. "STUDIES OF CROWN ETHER COMPLEXES; ARYLDIAZONIUM ION COMPLEXES". . p. 1775 - 1778. Retrieved 1980.
• 5、 Buschmann, H.-J.,Cleve, E.,Schollmeyer, E.. "The Complexation of Alkaline Cations by Crown Ethers and Cryptand in Acetone". . p. 569 - 578. Retrieved 1994.
• 6、 Greene. "". . p. 1793. Retrieved 1972.
• 7、 Hwang, Wen-Yu,Shih, Jeng-Shong. "Properties and applications of cryptand-22 surfactant for ion transport and ion extraction". . p. 1215 - 1222. Retrieved 2000.
• 8、 Caballo, Jorge,Gonzalez-Moreiras, Mariano,Mena, Miguel,Perez-Redondo, Adrian,Yelamos, Carlos. "Reactivity with electrophiles of imido groups supported on trinuclear titanium systems". . p. 11519 - 11529. Retrieved 2013.
• 9、 Jones, Brian A.,Bradshaw, Jerald S.,Brown, Philip R.,Christensen, James J.,Izatt, Reed M.. "Preparation of Macrocyclic Polyether-Thiono Diester and -Thiono Tetraester Ligands Containing either the Pyridine Subcyclic Unit or the Oxalyl Moiety, Their Complexes, and Their Reductive Desulfurization to Crown Ethers". . p. 2635 - 2639. Retrieved 1983.
• 10、 Gokel,Cram. "". . p. 2445. Retrieved 1974.