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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
BCCG8994
BCCG2076
BCCG1292
BCCF8030
BCCF4006

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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)
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.
T Colomina et al.
Veterinary and human toxicology, 33(2), 121-124 (1991-04-01)
The effects of repeated ip administration of diethylenetriaminepentaacetic acid (DTPA), Kryptofix 222, 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6), ethylenglycol-bis-(beta-amino-ethylether)-N,N'-tetraacetic acid (EGTA), and Kryptofix 5 on the distribution and excretion of sc-injected strontium were investigated in male Swiss mice. Groups of 20 animals received 95
T Chaly et al.
International journal of radiation applications and instrumentation. Part B, Nuclear medicine and biology, 16(4), 385-387 (1989-01-01)
A simple procedure for the detection of 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo (8.8.8) hexacosane (Kryptofix 2.2.2) in the final solution of [18F]FDG prepared by the aminopolyether supported nucleophilic substitution of 1,3,4,6-tetra-O-acetyl 2-O-trifluoromethanesulfonyl-beta-D-mannopyranose (Hamacher et al., 1986) has been developed. Presence of Kryptofix 2.2.2 in
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