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291110

Sigma-Aldrich

4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane

98%

Synonym(s):

Cryptand 222, Kryptofix® 222

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About This Item

Empirical Formula (Hill Notation):
C18H36N2O6
CAS Number:
23978-09-8
Molecular Weight:
376.49
Beilstein:
620282
EC Number:
245-962-4
MDL number:
MFCD00005111
UNSPSC Code:
12352005
PubChem Substance ID:
24857512
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

mp

68-71 °C (lit.)

SMILES string

C1COCCN2CCOCCOCCN(CCO1)CCOCCOCC2

InChI

1S/C18H36N2O6/c1-7-21-13-14-24-10-4-20-5-11-25-17-15-22-8-2-19(1)3-9-23-16-18-26-12-6-20/h1-18H2

InChI key

AUFVJZSDSXXFOI-UHFFFAOYSA-N

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General description

4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane(cryptand 222, Kryptofix 222) is an organic compound with formula C18H36N2O6. This compound has a cage-like three-dimensional structure that donates N2O6. The ligand has shown a wide range of uses in magnetic resonance imaging, organic synthesis, crystallography, electrochemistry, and chromatography. In solution, it is a well-known sequestering agent for metal ions.

Application

4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane is used as:

  • A electrolyte additive in isotachophoresis[separation method that is particularly suited to the analysis of small ions]for the analysis of alkali metal cations.
  • A complexing agent in the preparation of K+-imprinted nanoparticles using methacrylic acid as the functional monomer, ethylene glycol dimethacrylate as the crosslinker and 2,2′-azobisisobutyronitrile as the radical initiator.
  • A structure directing agent (SDA) in the preparation of LTA-type AlPO4 crystals.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.
Cryptand used with potassium mirror to reduce a hindered distannene to a crystalline radical anion.

Legal Information

Kryptofix is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2233
BCCL3568
BCCL1881
BCCJ8149
BCCH8282

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Metal Ion Compiexing by Cryptand 222 in Solutions. A Thermodynamic Approach
Marcus Y
Reviews in Analytical Chemistry, 23, 269-302 (2004)
Preparation of large and well-shaped LTA-type AlPO4 crystals by using crown ether Kryptofix 222 as structure directing agent
Huang A, et al.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 129, 90-99 (2010)
Preparation of a K+-imprinted polymer for the selective recognition of K+ in food samples
Hashemi B, et al.
Journal of Separation Science, 39, 2006-2012 (2016)
Vladimir Ya Lee et al.
Journal of the American Chemical Society, 128(35), 11643-11651 (2006-08-31)
((t)Bu(2)MeSi)(2)Sn=Sn(SiMe(t)Bu(2))(2) 1, prepared by the reaction of (t)Bu(2)MeSiNa with SnCl(2)-diox in THF and isolated as dark-green crystals, represents the first example of acyclic distannene with a Sn=Sn double bond that is stable both in the crystalline form and in solution.
D Pan et al.
Bioorganic & medicinal chemistry letters, 8(11), 1317-1320 (1999-01-01)
5'-Deoxy-5'-fluoro-O4-methylthymidine was synthesized by the reaction of the corresponding 5'-O-tosylate with KF in the presence of Kryptofix [222] and coupled to a 5'-phosphoramidite-activated CPG-bound oligodeoxynucleotide. The sequence of reactions and purifications were accomplished within 4 h, a necessary condition of
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