4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane TCI H0932

Chemical Identity

CAS No.: 23978-09-8
PubChem: CID 72801·SID 87571288
Formula: C18H36N2O6
Molecular weight: 376.5 g/mol
Purity: >98.0%(GC)(T)
Reference databases: ChemSpider·ECHA·Wikipedia

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane
SMILES: C1COCCOCCN2CCOCCOCCN1CCOCCOCC2
InChIKey: AUFVJZSDSXXFOI-UHFFFAOYSA-N

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4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane is a macrobicyclic cryptand: a three-dimensional cage-shaped ligand built from two bridgehead nitrogen atoms and six ether oxygen atoms arranged across three connecting chains. The cavity enclosed by this cage is able to trap alkali metal cations with a binding strength far exceeding that of ordinary crown ethers. In the laboratory, the compound serves as a tool for separating a cation from its partner anion — thereby making that anion far more reactive — or for dissolving inorganic salts into organic solvents that would not normally dissolve them.

The properties that make this reagent highly valued are its selectivity and its complexing strength. The cavity size of this cryptand is best matched to the potassium ion, so the compound binds potassium with very high affinity and shows clear discrimination against both sodium and lithium. Because the cation is tightly confined inside the cage, the anion left behind becomes almost naked and its nucleophilic reactivity increases dramatically — a phenomenon known as anion activation. The compound exists as a solid with a low melting point.

In Indonesian laboratories, this reagent is typically found in synthetic organic chemistry groups, university research laboratories, and institutional research facilities where phase-transfer chemistry and selective cation binding are part of the routine workflow. It is generally ordered in small quantities appropriate to its role as a specialty reagent rather than a bulk chemical, and is handled alongside other cation-binding ligands such as crown ethers within the same reagent inventory.

TCI brochures (PDF)

Hole-injection and Charge-generation Material with Strong Electron-Accepting Ability HAT-CN 6 2024-10-21 · p. 2
Macrocycles for Host-Guest Chemistry 2026-03-24 · p. 4

Related TCI products

Alkali metal cation complexation studies — the cryptand cage binds alkali cations far more strongly than crown ethers, allowing clean investigation of host–guest binding behaviour.
Selective potassium binding — the cavity dimensions of this cryptand match the potassium ion, giving very high affinity and clear discrimination against sodium and lithium in mixed systems.
Anion activation in organic synthesis — sequestering the cation inside the cage leaves an almost naked, highly nucleophilic anion, sharply increasing reaction rates for anionic reagents.
Solubilisation of inorganic salts in organic media — the reagent carries salts into organic solvents that would not normally dissolve them, enabling homogeneous reaction conditions.
Cation–anion separation for mechanistic work — separating a cation from its partner anion lets chemists study the intrinsic reactivity of the anion free from ion-pairing effects.

Brand	TCI
CAS number	23978-09-8
Molecular formula	—
Purity	—
Category	Chemistry > Synthetic Reagents > Chelation/Complexation Compounds
Pack sizes	available in standard TCI catalogue pack sizes; please confirm the size required when ordering
Physical form	solid with a low melting point
Storage	store in a tightly closed container in a cool, dry place away from moisture

Store this reagent in a tightly closed original container in a cool, dry area, protected from moisture and kept away from heat sources and direct sunlight. Because the material is a solid with a low melting point, avoid storage locations subject to elevated ambient temperature. Use glass or other chemically compatible containers and reseal promptly after each use to limit exposure to atmospheric moisture. Handle in a fume hood using standard personal protective equipment — safety glasses, gloves, and a laboratory coat — and avoid contact with skin, eyes, and clothing. Weigh and transfer with clean, dry spatulas to prevent contamination of the stock. Consult the manufacturer's safety data sheet before use and follow institutional procedures for chemical waste disposal.

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