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274984 Aldrich

18-Crown-6

≥99.0%

Synonym: 1,4,7,10,13,16-Hexaoxacyclooctadecane

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Properties

Related Categories Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers, Synthetic Reagents
assay   ≥99.0%
mp   42-45 °C(lit.)

Description

Application

Can be useful as phase-transfer catalysts.

Complexing agent which solubilizes cations in non-polar solvents.

Other Notes

Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations).

Packaging

1 g in glass bottle

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
3
RTECS 
MP4500000
Flash Point(F) 
>235.4 °F
Flash Point(C) 
>113 °C

Protocols & Articles

Peer-Reviewed Papers

References

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Gokel, G.W. Crown Ethers and Cryptands Cambridge, England , (1991)

Host-Guest Chemistry: Complexes between organic compounds simulate the substrate selectivity of enzymes. Cram, D.J. and Cram, J.M. Science 183, 803, (1974)

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An efficient fluorescence sensor for superoxide with an acridinium ion-linked porphyrin triad. Kotani H, Ohkubo K, Crossley MJ, et al. J. Am. Chem. Soc. 133(29), 11092-5, (2011)

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High-throughput capillary electrophoresis-mass spectrometry: from analysis of amino acids to analysis of protein complexes. Moini M Methods Mol. Biol. 984, 79-119, (2013)

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Insight into the dinuclear {Fe(NO)2}10{Fe(NO)2}10 and mononuclear {Fe(NO)2}10 dinitrosyliron complexes. Yeh SW, Lin CW, Li YW, et al. Inorg. Chem. 51(7), 4076-87, (2012)

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Precision synthesis of poly(3-hexylthiophene) from catalyst-transfer Suzuki-Miyaura coupling polymerization. Yokozawa T, Suzuki R, Nojima M, et al. Macromol. Rapid Commun. 32(11), 801-6, (2011)

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Computational modeling of capillary electrophoretic behavior of primary amines using dual system of 18-crown-6 and β-cyclodextrin. Elbashir AA and Suliman FO J. Chromatogr. A 1218(31), 5344-51, (2011)

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Supramolecular rotators of (aniliniums)([18]crown-6) in electrically conducting [Ni(dmit)2] crystals. Hoshino N, Yoshii Y, Aonuma M, et al. Inorg. Chem. 51(23), 12968-75, (2012)

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Structural and energetic effects in the molecular recognition of protonated peptidomimetic bases by 18-crown-6. Chen Y and Rodgers MT J. Am. Chem. Soc. 134(4), 2313-24, (2012)

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Conformational analysis of 18-azacrown-6 and its bonding with late first transition series divalent metals: insight from DFT combined with NPA and QTAIM analyses. Varadwaj PR, Varadwaj A, Peslherbe GH, et al. J. Phys. Chem. A 115(45), 13180-90, (2011)

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Diameter-sorted SWCNT-porphyrin and SWCNT-phthalocyanine conjugates for light-energy harvesting. Sandanayaka AS, Subbaiyan NK, Das SK, et al. ChemPhysChem 12(12), 2266-73, (2011)

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Structural and energetic effects in the molecular recognition of amino acids by 18-crown-6. Chen Y and Rodgers MT J. Am. Chem. Soc. 134(13), 5863-75, (2012)

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Antitumor potential of crown ethers: structure-activity relationships, cell cycle disturbances, and cell death studies of a series of ionophores. Marko Marjanovi? et al J. Med. Chem. 50, 1007-18, (2007)

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Intervalence charge transfer in mixed valence compound modified by the formation of a supramolecular complex. Mechouet M, Perruchot C, Maurel F, et al. J. Phys. Chem. A 116(3), 970-8, (2012)

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Preliminary studies of an 18-crown-6 ether modified magnetic cation exchange polymer in rapid (90)Sr bioassay. Hrdina A, Lai E, Li C, et al. Health Phys. 101(2), 187-95, (2011)

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Synergistic co-entrapment and triggered release in hollow nanocapsules with uniform nanopores. Dergunov SA and Pinkhassik E J. Am. Chem. Soc. 133(49), 19656-9, (2011)

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Novel axially disubstituted non-aggregated silicon phthalocyanines. Bıyıklıoğlu Z and Cakır D Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 98, 178-82, (2012)

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Structural and energetic effects in the molecular recognition of acetylated amino acids by 18-crown-6. Chen Y and Rodgers MT J. Am. Soc. Mass Spectrom. 23(11), 2020-30, (2012)

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Crown complexation of protonated amino acids: influence on IRMPD spectra. Stedwell CN, Galindo JF, Gulyuz K, et al. J. Phys. Chem. A 117(6), 1181-8, (2013)

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Lipase-catalyzed synthesis of hydrophobically modified dextrans: activity and regioselectivity of lipase from Candida rugosa. Kaewprapan K, Wongkongkatep J, Panbangred W, et al. J. Biosci. Bioeng. 112(2), 124-9, (2011)

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Could LogP be a principal determinant of biological activity in 18-crown-6 ethers? Synthesis of biologically active adamantane-substituted diaza-crowns. Fran Supek et al Eur. J. Med. Chem. 46, 3444-54, (2011)

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Toxicological responses of the earthworm Eisenia fetida to 18-crown-6 under laboratory conditions. Du Y, Rao P, Li Y, et al. Bull. Environ. Contam. Toxicol. 93(4), 452-5, (2014)

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In situ synthesis, photometric and spectroscopic studies of chelating system during the 1,4,7,10,13,16-hexaoxacyclooctadecane charge transfer reaction with different acceptors. Hossan AS, Abou-Melha HM, and Refat MS Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 79(3), 583-93, (2011)

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Synthesis of N-(2-chloro purin-6-yl) aza-18-crown-6 and its interaction with human serum albumin. Li C, Cui F, Mao R, et al. Org. Biomol. Chem. 10(4), 869-75, (2012)

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Host-guest chemistry in the gas phase: complex formation with 18-crown-6 enhances helicity of alanine-based peptides. Ko JY, Heo SW, Lee JH, et al. J. Phys. Chem. A 115(49), 14215-20, (2011)

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Complexes of amino acids with a crown-ether derivative of 4-styrylpyridine. Monotopic or ditopic? Fedorova OA, Fedorov YV, Labazava IE, et al. Photochem. Photobiol. Sci. 10(12), 1954-62, (2011)

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Quantization of bovine serum albumin by fluorescence enhancement effects and corresponding binding of macrocyclic host-protein assembly. Bardhan M, Misra T, and Ganguly T J. Photochem. Photobiol. B, Biol. 106, 113-9, (2012)

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Allylation of functionalized aldehydes by potassium allyltrifluoroborate catalyzed by 18-crown-6 in aqueous media. Barbosa FC, Freitas JC, Melo CF, et al. Molecules 17(12), 14099-110, (2012)

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Indirect UV detection-ion-exclusion/cation-exchange chromatography of common inorganic ions with sulfosalicylic acid eluent. Kozaki D, Mori M, Nakatani N, et al. Anal. Sci. 29(1), 121-6, (2013)

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Beil. 19,V,12,601

Fieser 4,142 / Fieser 5,152 / Fieser 6,133 / Fieser 7,76 / Fieser 8,128 / Fieser 9,126 / Fieser 10,110

Aldrich MSDS 1, 494:A / Corp MSDS 1 (1), 929:A / FT-IR 1 (1), 253:B / FT-IR 2 (1), 403:D / IR-Spectra (3), 147:B / IR-Spectra (2), 132:F / NMR-Reference 2 (1), 212:B / RegBook 1 (1), 271:B / Sax 6, 818 / Sigma FT-IR 1 (2), 408:C / Structure Index 1, 37:D:2

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