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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Dynamers at the solid-liquid interface: controlling the reversible assembly/reassembly process between two highly ordered supramolecular guanine motifs.
Artur Ciesielski et al.
Angewandte Chemie (International ed. in English), 49(11), 1963-1966 (2010-02-06)
Jeff E Prest et al.
Journal of chromatography. A, 1260, 239-243 (2012-09-20)
This work shows how the inclusion of cryptand 222 as a leading electrolyte additive in isotachophoresis affects the electrophoretic mobilities of alkali metal cations. Using isotachophoresis the separation of alkali metals can be difficult due to the similar electrophoretic mobilities
Direct analysis of Kryptofix 2.2.2 in 18FDG by gas chromatography using a nitrogen-selective detector.
R A Ferrieri et al.
Nuclear medicine and biology, 20(3), 367-369 (1993-04-01)
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