58966-93-1 Usage
Uses
1,4,7-Triazacyclononane Trihydrochloride is a useful compound in the organic synthesis of ligands and compounds requiring a triazacyclononane group.
Application
1,4,7-Triazacyclononane trihydrochloride can be used as a reagent to prepare:Nonadentate ligand, 1,4,7-tris[(6-carboxypyridin-2-yl)methyl]-1,4,7-triazacyclononane (H3tpatcn), which is used to prepare lanthanide complexes with high water solubility and rigid C3 symmetric structures.Dansyl cryptands as fluorescent indicators via amination of (bromobenzyl)triazacycloalkane and oxadiamines.[1,4,7-tri(3-butenyl)-1,4,7-triazacyclononane and 1,4,7-tri(2-propenyl)-1,4,7-triazacyclononane] by reacting with corresponding alkenyl halide.
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.
A Bis-Triazacyclononane Tris-Pyridyl N9-Azacryptand “Beer Can” Receptor for Complexation of Alkali Metal and Lead(II) Cations
Brown, Asha,Bunchuay, Thanthapatra,Crane, Christopher G.,White, Nicholas G.,Thompson, Amber L.,Beer, Paul D.
supporting information, p. 10434 - 10442 (2018/07/31)
A new bis-triazacyclononane tris-pyridyl N9-azacryptand ligand is prepared via a convenient one-pot [2+3] condensation reaction between triazacyclononane and 2,6-bis(bromomethyl) pyridine in the presence of M2CO3 (M=Li, Na, K). The proton, lithium, sodium, potassium and lead(II) complexes of the ligand are characterised in the solid state. Preliminary solution-phase competition experiments indicate that the cryptand ligand preferentially binds lead(II) in the presence of sodium, calcium, potassium and zinc cations in methanol solution.
