51-46-7

Usage

Uses

Used in Metal Ion Complexing and Stabilization:
1,3,5,7-Tetraazatricyclo[3.3.2.23,7]dodecane is used as a complexing agent and stabilizer for metal ions, specifically copper and nickel, due to its ability to form stable complexes. This property is crucial in various industrial processes, such as metal plating, where it helps in achieving uniform and adherent metal coatings.
Used in Corrosion Inhibition:
In the industry, 1,3,5,7-Tetraazatricyclo[3.3.2.23,7]dodecane is used as a corrosion inhibitor. Its interaction with metal surfaces helps to prevent or reduce the rate of corrosion, thereby extending the service life of metal components and structures.
Used in Synthesis of Coordination Polymers:
1,3,5,7-Tetraazatricyclo[3.3.2.23,7]dodecane is utilized in the synthesis of coordination polymers, which are compounds with repeating units of metal ions connected by organic ligands. These polymers have potential applications in areas such as catalysis, materials science, and drug delivery.
Used in Coordination Chemistry Research:
As a ligand, 1,3,5,7-Tetraazatricyclo[3.3.2.23,7]dodecane is used in coordination chemistry studies. Its cage-like structure allows for the exploration of new coordination modes and the development of novel metal complexes with potential applications in various fields.
Used in Molecular Imaging:
1,3,5,7-Tetraazatricyclo[3.3.2.23,7]dodecane has potential applications in the field of molecular imaging. Its ability to form stable complexes with metal ions can be leveraged to develop contrast agents for imaging techniques such as magnetic resonance imaging (MRI) or computed tomography (CT).
Used as a Chelating Agent in the Medical Industry:
In the medical field, 1,3,5,7-Tetraazatricyclo[3.3.2.23,7]dodecane is considered for use as a chelating agent. Its capacity to bind metal ions can be beneficial in the treatment of heavy metal poisoning or in the development of drugs that target specific metal-containing enzymes or receptors.
Despite these promising applications, the commercial availability of 1,3,5,7-Tetraazatricyclo[3.3.2.23,7]dodecane, or TATD, is currently limited, restricting its use primarily to specialized research and industrial applications.

InChI:InChI=1/C8H16N4/c1-2-10-7-11-3-4-12(8-10)6-9(1)5-11/h1-8H2

Upstream product

• 504-74-5 tetrahydroimidazole 
• 50-00-0 formaldehyd 
• 7732-18-5 water 
• 107-15-3 ethylenediamine 
• 67-56-1 methanol 

Downstream Products

• 6639-47-0 1,3,5-tris(p-tolyl)hexahydro-s-triazine 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 39809-82-0 N,N'-bis-(4-nitrophenyl)methanediamine 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 504-74-5 tetrahydroimidazole 
• 280-29-5 1,3,5-triazabicyclo[3.2.1]-octane 
• 100-97-0 hexamethylenetetramine 
• 125251-91-4 1,3,6,8-tetraazatricyclo[4.3.1.1^3,8]undecane 
• 14168-48-0 2,5-dinitro-2,5-diaza-1,6-hexanediyl diacetate 
• 494867-14-0 1-butyl-3,6-diazatricyclo[4.3.1.1^3,8]undecan-9-ol 
• 429648-41-9 1-butyl-3,6-diazatricyclo[4.3.1.1^3,8]undecan-9-one oxime 
• 169271-54-9 1-(p-hydroxybenzyl)-3,6-diazahomoadamantan-9-one 

Relevant academic research and scientific papers

Synthesis and characterization of novel bis-triazenes: 3,8-di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The reaction of diazonium ions with ethylenediamine/formaldehyde mixtures

Reaction of a diazonium salt solution with a mixture of ethylenediamine and an excess of formaldehyde or 1,3,6,8-tetraazatricyclo[4,4,1,13,8]dodecane results in the formation of a novel class of bis-triazenes, the 3,8-di(2-aryl-1-azenyl)-1,3,6,8-tetraazabicyclo[4.4.1]undecanes (6), which have been fully characterized by spectroscopy, elemental analysis, and X-ray crystallography. The X-ray data show that the tetraazabicyclic cage is folded back so that the aryl groups interact by π-π-stacking. The proton NMR spectra are made complex by the presence of three sets of distinctly different diastereotopic methylene groups, which have been assigned by a combination of decoupling and 2D-NMR experiments. In the case involving coupling of the p-anisidine diazonium derivative to ethylenediamine and formaldehyde mixtures, 1,3-di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine (8) was the only product isolated. Its structure has been assigned on the basis of 1H and 13C NMR spectra and X-ray crystallography.

An unusual product obtained from condensation between ethylenediamine and formaldehyde in basic medium

Reaction between ethylenediamine and formaldehyde normally affords 1,3,6,8-tetraazatricyclo[4.4.1.13.8]dodecane (TATD) but in this case also afforded 3,3′-ethane-1,2-diyl-bis-1,3,5-triazabicyclo[3.2.1]octane (ETABOC), this being an unusual prod

Synthesis of 4,5-dihydro-1,6:3,8-dimethano-1,3,6,8-benzotetrazecine

Three-component condensation of formaldehyde, o-phenylenediamine, and ethylenediamine gave for the first time 4,5-dihydro-1,6:3,8-dimethano-1,3,6,8- benzotetrazecine. Its structure was proved by X-ray diffraction analysis. A similar condensation of formaldehyde with a mixture of ethylenediamine and 1,2-diamino-4-methylbenzene yielded 10-methyl-4,5-dihydro-1,6:3,8-dimethano-1,3, 6,8-benzotetrazecine and a condensation with a mixture of o-phenylenediamine and propane-1,2-diamine yielded 4-methyl-4,5-dihydro-1,6:3,8-dimethano-1,3,6,8- benzotetrazecine.

Synthesis of heterobicyclic tetrakis- and bis-triazenes: Reaction between 3,3′-ethane-1,2-diylbis(1,3,5-triazabicyclo[3.2.1]octane) (ETABOC) with diazonium salts bearing electron donating groups

In this work, a coupling reaction of aryl diazonium salts with a poly-N-nucleophile is developed for the synthesis of a variety of heterobicyclic tetrakis- and bistriazene compounds. The transformation proceeds smoothly in basic medium with good and moderate yields. In addition to the expected 3,3′-methanediylbis{1,5-bis[(E)-aryldiazenyl]-1,3,5-triazepanes}, two classes of heterobicyclic bis-triazenes were obtained by two ring rearrangement reactions. Using this method, an unknown class of organic compounds containing the saturated bis(imidazolidinyl)-methane unit can be accessed efficiently.

Synthesis of fragrant 3,6-diazahomoadamantan-9-ones

A condensation of tetramethylenediethylenetetramine with 4-phenylbutan-2-one and its derivatives such as 4-(4-hydroxyphenyl)butan-2-one, 4-(4-methoxyphenyl)butan-2-one, and 4-(4-hydroxy-3-methoxyphenyl)butan-2-one led to fragrant compounds: 1-benzyl-3,6-d

Condensation of Alkanediamines with Formaldehyde; Intramolecular Disproportionation of N-Hydroxymethyl Groups into N-Methyl and N-Formyl Groups

The condensation of α,ω-alkanediamines NH2(CN2)nNH2 with aqueous formaldehyde has been studied by NMR spectroscopy of isolated products and of product mixtures.The condensation was reversible and gave products of widely different types depending on alkane chain length: bicyclic oxadiaza compounds (n = 2, 3, 4), a tricyclic tetraaza compound (n = 2), a quinquecyclic octaaza compound (n = 3), two-dimensional polymers (n = 4, 5).A slow irreversible rearrangement gave in two cases (n = 3, 4), unicyclic 1-formyl-3-methyl-1,3-diaza compounds.The condensation of N,N'-dimethyl-α,ω-alkandediamines CH3NH(CH2)nNHCH3 with aqueous formaldehyde was also studied.The reversible formation of simple unicyclic diaza compounds was observed in all cases (n = 2, 3, 4), but in one case (n = 2) there was again a slow irreversible rearrangement to the N-formyl-N,N'N'-trimethyl derivative.The rearrangement reaction involves a hydride shift and is strictly intramolecular.The conditions for its occurrence can be understood on a conformational basis.