15439-16-4

Usage

Uses

Used in Chemical Industry:
1,4,8,12-Tetraazacyclopentadecane is used as a chelating agent for its ability to form stable complexes with metal ions. This property makes it useful in various chemical processes, such as catalysis and separation techniques.
Used in Pharmaceutical Industry:
1,4,8,12-Tetraazacyclopentadecane is used as a building block for the synthesis of various pharmaceutical compounds, including those with potential applications in drug delivery and targeting.
Used in Analytical Chemistry:
1,4,8,12-Tetraazacyclopentadecane is used as a reagent in analytical chemistry for the detection and quantification of metal ions, due to its chelating properties.
Used in Environmental Applications:
1,4,8,12-Tetraazacyclopentadecane can be employed in environmental applications for the removal of heavy metal ions from contaminated water or soil, thanks to its ability to form stable complexes with these ions.
Used in Research and Development:
1,4,8,12-Tetraazacyclopentadecane serves as a valuable compound in research and development, particularly in the fields of supramolecular chemistry and coordination chemistry, where its unique structural properties can be exploited to design new materials and systems.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 5505, 1992 DOI: 10.1016/S0040-4039(00)61129-2

InChI:InChI=1/C11H26N4/c1-4-12-6-2-8-14-10-11-15-9-3-7-13-5-1/h12-15H,1-11H2/p+4

Upstream product

• 74676-47-4 N,N',N'',N'''-tetratosyl-1,10-diamino-4,7-diazadecane 
• 773837-37-9 sodium cyanide 
• 71901-51-4 [15]aneN₄(OH₂)2+ 
• 99708-68-6 [C₅H₄NCH₂Cr(C₁₁H₂₆N₄)(H₂O)]⁽²⁺⁾ 
• 99708-69-7 [(3-pyridylmethyl)Cr(1,4,8,12-tetraazacyclopentadecane)(H₂O)]⁽²⁺⁾ 
• 144534-68-9 C,C,C-Trifluoro-N-(3-trifluoromethanesulfonylamino-propyl)-N-{2-[trifluoromethanesulfonyl-(3-trifluoromethanesulfonylamino-propyl)-amino]-ethyl}-methanesulfonamide 
• 10563-26-5 N,N'-bis(3-aminopropyl)-1,2-diamine 
• 144534-72-5 1,4,8,12-Tetrakis-trifluoromethanesulfonyl-1,4,8,12-tetraaza-cyclopentadecane 
• 69038-12-6 1,4,8,12-tetrakis(p-tolylsulphonyl)-1,4,8,12-tetra-azacyclopentadecane 

Downstream Products

• 916148-26-0 [([15]aneN₄)Fe(II)(SPh)]BF₄ 
• 1073190-01-8 [Fe(II)(1,4,8,12-tetraazacyclopentadecane)(SC₆H₄-p-Cl)]BF₄ 
• 1073190-03-0 [Fe(II)([15]aneN₄)(SC₆H₄-p-OMe)]BF₄ 
• 1073190-07-4 [Fe(II)(1,4,8,12-tetraazacyclopentadecane)(SC₆H₄-p-NO₂)]BF₄ 
• 906005-45-6 [Zn(SCH₂C₆H₅)(1,4,8,12-tetraazacyclopentadecane)][ClO₄] 
• 77846-74-3 dichloro(1,4,8,12-tetraazacyclopentadecane)bis(triphenylphosphine)ruthenium(II) 
• 192518-28-8 Benzyl-(5-{4,8,12-tris-[5-(benzyl-tert-butoxycarbonyl-amino)-pentyl]-1,4,8,12-tetraaza-cyclopentadec-1-yl}-pentyl)-carbamic acid tert-butyl ester 
• 125262-44-4 1,4,8,12-tetrakis-(2-pyridylmethyl)-1,4,8,12-tetraazacyclopentadecane 
• 916148-26-0 [Fe(II)(1,4,8,12-tetraazacyclopentadecane)(SC₆H₅)]BF₄ 

Relevant academic research and scientific papers

Polyazamacrocyclic compounds for complexation of metal ions

The present invention relates to a new polyazamacrocyclic compound or a salt thereof and its uses. The compound has the formula STR1 where x is 2, 3 or a combination of p 2(s) and q 3(s) where p+q=y; y is 3 or 4; R is (CH2)z P(=0)R1 R2 ; R1 is R3 or OR3 where R3 is alkyl, cycloalkyl or aryl; R2 is H, alkyl or STR2 where R4 is alkyl, cycloalkyl or aryl; and z is 1 to 3. In one important embodiment, this compound may be complexed with a metal to be a polyazamacrocyclic compound-metal complex having the formula STR3 where r is 2 or 3; and Me is a metal ion.

Triflamides for protection and cyclization of tetraamines to tetraazamacrocycles

A facile two-step synthesis of tetraazamacrocycles is reported starting from trifluoromethanesulfonyl derivatives of linear tetraamines. After cyclization, the macrocycle was deprotected using sodium in liquid ammonia.

MACROHETEROCYCLES. 15.* SYNTHESIS OF MACROCYCLIC POLYAMINES IN A BIPHASIC SYSTEM

Macrocyclic polyamines are conveniently synthesized by condensation of bissulfonamides with ditosylates or dibromides of glycols in the biphasic system toluene(xylene)-aqueous sodium hydroxide.

MACROHETEROCYCLES. PART 44. FACILE SYNTHESIS OF AZACROWN ETHERS AND CRYPTANDS IN A TWO-PHASE SYSTEM

A facile procedure is proposed for the preparation of azacrown ethers and cryptands by condensation of dibromides or ethylene glycol bis(toluene-p-sulphonate)s with acyclic bis(sulphonamide)s or with bisdiazacrown ethers, respectively.The reaction was carried out in a two-phase system of aqueous alkali-toluene (benzene)in the presence of quaternary ammonium salts as phase transfer catalysts.The catalytic activity decreased in the sequence: Bu4NI ca.Bu4NBr > Bu4NCl > Bu4NHSO4 > Et3NCH2C6H5NCl.Maximum yields of twelve-membered azacrown ethers are obtained when lithium hydroxide is used, while crown ethers of larger size are observed in the presence of sodium or potassium hydroxides; this may be due to a template effect.

MACROHETEROCYCES. XXXVI. A CONVENIENT METHOD FOR SYNTHESIS OF DI- AND POLYAZACROWN ETHERS

A method is proposed for the production of di- and polyazacrown ethers by the condensation of bissulfonamides with dibromides or ditosyloxy derivatives in a two-phase aqueous alkali-toluene (benzene) system.The optimum concentration range for the substrate and the alkylating agent is 0.017-0.1 M.The catalytic activity of the quaternary ammonium salts decreases in the order (Bu)4NI > (Bu4)NBr > (Bu4)NCl > (Bu4)NHSO4 > (C2H5)3C6H5CH2NCl >> (Et)4NI > (Et)4NBr.The highest yields of te 12-membered azacrown ethers are obtained in the presence of lithium hyroxide, and the largest yields of the crown ethers with larger ring sizes are obtained in the presence of sodium or potassium hydroxide, and this is probably due to the matrix effects of the cation.

σ-Bonded organochromiuin(III) complexes. 3. Decomposition in acid solution of chromium(III) complexes containing pyridylmethyl and polydentate amine ligands

The decomposition of σ-bonded (pyridylmethyl)chromium complexes, 2- and 3-NC5H4CH2CrLn (L = dap (1,3-diaminopropane), dien (diethylenetriamine), trien (triethylenetetramine), and [15]aneN4 (tetraazacyclopentadecane)), was investigated in aqueous perchloric acid under aerobic conditions. Except for L = 15[ane]N4, Cr-C bond scission was preceded by complete aquation in the case of the 2-isomers and partial aquation for the 3-isomers. The aquation rates were compared with those of inorganic chromium complexes containing similar amine ligands. Kinetic data for the Cr-C bond cleavage were correlated with those for the analogous ethylenediamine (en) and aquo (H2O) systems. The activation parameters and product studies are in support of a homolytic pathway for the Cr-C bond cleavage.

A microcalorimetric determination of the enthalpies of formation in solution of nickel(II) complexes with tetraaza macrocyclic ligands of varying size

The enthalpies of formation of nickel complexes with tetraaza macrocyclic ligands of varying ring size, from 12 to 15 members, have been determined by destroying the complexes in aqueous solution with alkaline cyanide. The octahedral-square-planar equilibria have been investigated, and the results are presented as ΔH° for both octahedral, blue and, when possible, square-planar, yellow species. Like the Cu(II) system, the blue, octahedral series exhibits a maximum in ΔH° with [14]aneN4. This is discussed in terms of the relative size of the ligand and the metal ion. The unexpected reversal of ΔH° for the two square-planar complexes is rationalized in terms of expected ligand transformations.