78668-34-5

Basic information

• Product Name: 1,4,7,10-TETRAAZA-2,6-PYRIDINOPHANE
• Synonyms: 1,4,7,10-TETRAAZA-2,6-PYRIDINOPHANE;PYCLEN
• CAS NO: 78668-34-5
• Molecular Formula: C₁₁H₁₈N₄
• Molecular Weight: 206.29
• Mol File: 78668-34-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 366.5°C at 760 mmHg
• Flash Point: 175.4°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 1.46E-05mmHg at 25°C
• Refractive Index: 1.497
• PKA: 9.69±0.20(Predicted)
• CAS DataBase Reference: 1,4,7,10-TETRAAZA-2,6-PYRIDINOPHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,7,10-TETRAAZA-2,6-PYRIDINOPHANE(78668-34-5)
• EPA Substance Registry System: 1,4,7,10-TETRAAZA-2,6-PYRIDINOPHANE(78668-34-5)

Safety Data

• Hazardous Substances Data: 78668-34-5(Hazardous Substances Data)

Usage

General Description

1,4,7,10-Tetraaza-2,6-pyridinophane is a chemical compound part of the macrocycle family, specifically a tetraazamacrocycle. These chemicals are often characterized by their large cyclic structures, with nitrogen atoms interspersed within the ring. 1,4,7,10-Tetraaza-2,6-pyridinophane has been utilized in research due to its strong ability to bind and sequester certain metal ions, particularly transition metals. This complexing ability makes it relevant in various scientific fields including biology, medicine, and materials science. Further, it serves as an effective ligand in inorganic chemistry due to its cyclic structure and the potential for donation of electron pairs from the nitrogen atoms.

InChI:InChI=1/C11H18N4/c1-2-10-8-13-6-4-12-5-7-14-9-11(3-1)15-10/h1-3,12-14H,4-9H2

Upstream product

• 3099-28-3 2,6-bis(chloromethyl)pyridine 
• 55667-74-8 pyridine-2,6-diylbis(methylene)dimethanesulfonate 
• 56187-04-3 1,4,7-tritosyl-1,4,7-triazaheptane 
• 34984-16-2 2,6-bis(aminomethyl)pyridine 
• 78668-28-7 3,6,9-tris-(toluene-4-sulfonyl)-3,6,9,15-tetraaza-bicyclo[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-triene 
• 1195-59-1 2.6-bis(hydroxymethyl)pyridine 
• 7703-74-4 2,6-bis-(bromomethyl)pyridine 
• 290326-06-6 3,6,9-tris-(2-nitro-benzenesulfonyl)-3,6,9,15-tetraaza-bicyclo[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-triene 

Downstream Products

• 107-21-1 ethylene glycol 
• 910449-96-6 2-(6,9-bis(ethoxycarbonylmethyl)-3,6,9,15-tetraazabicyclo-[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-trien-3-yl)-4-(4-nitrophenyl)butyric acid, methyl ester of 
• 596121-70-9 4-(4-nitrophenyl)-2-(3,6,9,15-tetraazabicyclo-[9.3.1]pentadeca-1⁽¹⁴⁾,11⁽¹⁵⁾,12-trien-3-yl)butyric acid, methyl ester of 

Relevant articles and documents

The role of the capping bond effect on pyclen natY3+/90Y3+ chelates: Full control of the regiospecific: N -functionalization makes the difference

Thanks to a smart regiospecific N-functionalization, a pyclen based ligand bearing one picolinate and two acetate arms organized in a dissymmetric manner was synthesized for Y3+ complexation, and compared to its symmetric analogue. The nature of the capping bonds around the metal coordination environment has a dramatic effect on the properties of the chelate, the natY3+ and 90Y3+ dissymmetric derivatives presenting enhanced thermodynamic stability and kinetic inertness.

Seven coordinate Co(ii) and six coordinate Ni(ii) complexes of an aromatic macrocyclic triamide ligand as paraCEST agents for MRI

We are reporting Co(ii) and Ni(ii) complexes of a pyridine containing aromatic macrocyclic triamide ligand, 3,6,9,15-tetraazabicyclo(9.3.1)pentadeca-1(15),11,13-triene-3,6,9-triacetamide (TPTA), as paramagnetic chemical exchange saturation transfer (paraCEST) MRI contrast agents. The synthesis and characterization of TPTA and its complexes are reported. The solution chemistry and solid-state structure of Co(ii) and Ni(ii) complexes are studied. Crystallographic data show that the [Co(TPTA)]·Cl2·2H2O complex (seven-coordinate, all four N atoms of ring and three amide O atoms) has a distorted pentagonal bipyramidal geometry, however the [Ni(TPTA)Cl]·Cl·0.25H2O complex (six-coordinate, all four N atoms of the ring, one amide O and one chloride ion) adopts a distorted octahedral geometry. Notably the two pendent amide arms are not coordinated in the [Ni(TPTA)Cl]+ complex and one chloride ion fulfils its sixth coordination. The CEST effect of [Co(TPTA)]2+ and [Ni(TPTA)Cl]+ amide protons is observed at 57 ppm and 78 ppm downfield of the bulk water proton respectively in a buffer solution containing 20 mM N-(2-hydroxyethyl)piperazine-N′-ethanesulfonic acid and 100 mM NaCl at pH 7.4 at 37 °C on a 9.4 T NMR spectrometer. The effects of CEST intensity and exchange rate constant with variation of pH of the solution were studied. The CEST effect and exchange rate constant for the amide protons of the [Co(TPTA)]2+ complex have been monitored in HEPES buffer, fetal bovine serum (FBS), rabbit serum and 4% agarose gel (w/w). The stability of the [Co(TPTA)]2+ complex in aqueous solution towards oxidation was verified by cyclic voltammetry measurement. The stability of [Co(TPTA)]2+ has further been monitored in the presence of biologically relevant ions including HPO42-, CO32-, and Zn2+ and under acidic conditions.

Method for preparing 1,4,7,10-tetraaza-2,6-pyridinophane

The invention relates to a novel method for preparing 1,4,7,10-tetraaza-2,6-pyridinophane. 2,6-dimethylamino pyridine serving as a raw material is subjected to amino protection through o-/p-nitrobenzenesulfonyl and reacts with N,N-di(2-chloroethyl)-o-/p-n