58966-93-1 Usage
Description
1,4,7-Triazacyclononane Trihydrochloride is a chemical compound characterized by its triazacyclononane group, which is a nine-membered ring containing three nitrogen atoms. 1,4,7-TRIAZACYCLONONANE TRIHYDROCHLORIDE is a versatile building block in organic synthesis and is widely utilized in the creation of various ligands and complex molecules.
Uses
Used in Organic Synthesis:
1,4,7-Triazacyclononane Trihydrochloride is used as a reagent for the preparation of complex organic compounds that require a triazacyclononane group. Its unique structure and properties make it a valuable component in the synthesis of various ligands and molecules.
Used in the Preparation of Lanthanide Complexes:
1,4,7-Triazacyclononane Trihydrochloride is used as a reagent to prepare the nonadentate ligand, 1,4,7-tris[(6-carboxypyridin-2-yl)methyl]-1,4,7-triazacyclononane (H3tpatcn). This ligand is essential for the synthesis of lanthanide complexes with high water solubility and rigid C3 symmetric structures, which are crucial in various applications, including medical imaging and analytical chemistry.
Used in the Synthesis of Dansyl Cryptands:
1,4,7-Triazacyclononane Trihydrochloride is also used in the synthesis of Dansyl cryptands, which serve as fluorescent indicators. This is achieved through the amination of (bromobenzyl)triazacycloalkane and oxadiamines, resulting in a versatile and sensitive tool for various analytical and diagnostic applications.
Used in the Synthesis of Triazacyclononane-Derived Compounds:
1,4,7-Triazacyclononane Trihydrochloride can be reacted with corresponding alkenyl halides to produce [1,4,7-tri(3-butenyl)-1,4,7-triazacyclononane and 1,4,7-tri(2-propenyl)-1,4,7-triazacyclononane]. These compounds have potential applications in various fields, including pharmaceuticals, materials science, and catalysis, due to their unique structural features and reactivity.
storage
This nitrogen crown ether analog, also known as octahydro-1h-1,4,7-triazonine trihydrochloride should be stored in a cool and dark place. Keep under inert gas and protect from moisture. 1,4,7-Triazacyclononane Trihydrochloride is known to be incompatible with oxidizing agents and should not be stored or handled in their vicinity.
Preparation
Synthesis of 1,4,7-Triazacyclononane trihydrochloride (tacn.3HCl) A round bottom flask (1 L) was charged with 18M H2SO4 (450 mL) and 1,4,7-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane (4) (138.8 g, 0.234 mol) added in small portions (approximately 10 g every 5 min). The mixture was heated with stirring in a heat block for 3 days at 120°C. The resulting black solution was cooled to room temperature and added dropwise using a dropping funnel to a vigorously stirred mixture of cold absolute EtOH/Et2O (1.5 L/900 mL) cooled in an ice bath. An overhead stirrer was used to ensure efficient stirring. A sticky hygroscopic brown/grey precipitate formed, which was isolated quickly by vacuum filtration and immediately dissolved in de–ionised H2O (1 L). The mixture was heated for 2 h at 60°C. The mixture was then cooled to room temperature, filtered through Celite and the resulting solution concentrated to 250 mL under reduced pressure at 65°C. Conc. HCl (200 mL) was added followed by absolute EtOH until the solution became cloudy. The mixture was stored at 4°C overnight to promote precipitation. The white precipitate was collected by filtration and washed with ice cold absolute EtOH (3 x 50 mL), followed by Et2O (2 x 50 mL) to yield tacn.3HCl (5) as a white crystalline powder. Yield 44.9 g (80%).mp. 268.1–270.0°C (Lit.4 mp. 280–281°C). 1H NMR (300 MHz, D2O) δH 3.48 (12H, s, CH2). 13C NMR (75 MHz, D2O) δC 43.1 (CH2). ESI–MS m/z [M + H]+ 130.1. The 1H and 13C NMR spectral data were consistent with literature data.Using iSUSTAIN(TM) to validate the chemical attributes of different approaches to the synthesis of tacn and bridged bis(tacn) ligands
Check Digit Verification of cas no
The CAS Registry Mumber 58966-93-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,9,6 and 6 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 58966-93:
(7*5)+(6*8)+(5*9)+(4*6)+(3*6)+(2*9)+(1*3)=191
191 % 10 = 1
So 58966-93-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H15N3.3ClH/c1-2-8-5-6-9-4-3-7-1;;;/h7-9H,1-6H2;3*1H
58966-93-1Relevant articles and documents
Rapid and high yield detosylation of linear and macrocyclic p-toluenesulfonamides
Lazar
, p. 3181 - 3185 (1995)
Rapid and high yield detosylation of linear and macrocyclic p-toluenesulfonamides were achieved by heating their approximately 50% concentrated sulfuric acid solution at 170-180°C for 5-8 min.
METHOD FOR PREPARING NOTA DERIVATIVE
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Paragraph 0046, (2019/08/14)
The present invention discloses Method for preparing NOTA derivative. Firstly, take 4-methylsulfonyl chloride and diethylenetriamine in tosyl group reaction to obtain the first product. And, take the first product and sodium methoxide in the first substitution reaction to obtain the second product. Further, take 4-methylsulfonyl chloride and ethylene glycol in tosyl group reaction to obtain a third product. The second product is coupled to the third product to obtain a fourth product. Take the fourth product and sulfuric acid in the second substitution reaction. Finally, a final product is obtained by a bonding reaction with hydrochloric acid. The preparation method improves the water absorption issue of the benzene ring structure compound (TACN) of the NOTA derivative.
Comparative studies of the electronic, binding and photophysical properties of a new nona-dentate hemi-cage tripodal HQ pendant trizaza-macrocycle with unfilled, half-filled and completely filled lanthanide ions
Baral, Minati,Kanungo, B. K.,Rohini
, p. 16040 - 16059 (2018/10/04)
The present paper describes the comparative studies of the electronic, photophysical and binding properties of a new C3-symmetric polydentate ligand, 1,4,7-tris-{(5-methylene-8-hydroxyquinoline)-1,4,7-triazacyclononane} (9N3Me5Ox), and its complexes with 4f0, 4f7, and 4f14 metal ions (La3+, Gd3+, and Lu3+) by experimental and theoretical methods using DFT, TDDFT, TDDFTB, ETS-NOCV, NBO and Ligand Field DFT (LFDFT). The ligand and the complexes were synthesized and characterized through elemental analysis, molar conductance, TGA, FT-IR, FT-NMR, 1H-1H COSY and ESI-mass spectrometry techniques. The spectral data and structural studies revealed the formation of nine-coordinate compounds with the general formula [Ln(9N3Me5Ox)(H2O)3], in which the nonadentate chelator acted as a trinegative hexadentate ligand coordinating to the metal ions through three sets of O,N-donors of 8-hydroxyquinoline groups and three coordinated water molecules. The molecular modeling studies suggest that the metal ion can be easily encapsulated in its central cavity forming hemi-cage complexes without altering the basic metal-ligand coordination sphere. The nature of the bonding between the lanthanide ions and 9N3Me5Ox3?, elucidated by means of the natural bond orbital (NBO), Morokuma-Ziegler energy decomposition analysis (ETS-NOCV) scheme, suggests that the Ln-L bonds are more electrostatic (～82percent) than covalent (～18percent). The covalent character of the complexes increases in the order Lu > La > Gd. The photoluminescence spectral studies of the metal complexes revealed that the observed luminescence of the compounds in the solid state and solution is of different origin. The vibrational, 1H and 13C NMR spectral data obtained from the DFT optimized structures showed good agreement with the experimental results. The excitation and emission behaviours of the ligand and the complexes were established by molecular orbital analysis of the ground state DFT geometry as well as of the excited state optimized geometry using TD-DFT and TD-DFTB orbital analysis, excitation and emission properties.
