1,4,7-Triazacyclononane

Base Information

• Chemical Name: 1,4,7-Triazacyclononane
• CAS No.: 4730-54-5
• Molecular Formula: C6H15N3
• Molecular Weight: 129.205
• Hs Code.: 2933990090
• European Community (EC) Number: 637-157-5
• NSC Number: 681101
• UNII: 2UIF93C5H3
• DSSTox Substance ID: DTXSID50197095
• Nikkaji Number: J351.553B
• Wikipedia: 1,4,7-Triazacyclononane
• Wikidata: Q4545690
• Metabolomics Workbench ID: 55567
• ChEMBL ID: CHEMBL1650628
• Mol file: 4730-54-5.mol

Synonyms:NSC 681101;Octahydro-1H-1,4,7-triazonine;

Chemical Property of 1,4,7-Triazacyclononane

Chemical Property:

• Vapor Pressure: 0.0176mmHg at 25°C
• Melting Point: 42-45 °C(lit.)
• Refractive Index: 1.424
• Boiling Point: 254.094 °C at 760 mmHg
• PKA: 10.57±0.20(Predicted)
• Flash Point: 87.162 °C
• PSA: 36.09000
• Density: 0.874 g/cm³
• LogP: -0.24480
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 129.126597491
• Heavy Atom Count: 9
• Complexity: 45.1

Purity/Quality:

98% ^*data from raw suppliers

1,4,7-Triazonane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1CNCCNCCN1
• Description: 1,4,7-Triazacyclononane, known as "TACN" which is pronounced "tack-en," is a cyclic organic compound with the formula C6H12(NH)3. TACN is derived, formally speaking, from cyclononane by replacing three equidistant CH2 groups with NH groups. TACN is one of the oligomers derived from aziridine, C2H4NH. Other members of the series include diazacyclohexane, C4H8(NH)2, and the cyclic tetramer 1,4,7,10-tetraazacyclododecane.
• Uses: Starting material for the synthesis of 1,4,7-trifunctionalized derivatives which have applications in metal complexation. 1,4,7-Triazacyclononane (TACN) is a versatile platform from which various ligands can be derived to form effective chelators for (radio)copper(II) complexation. The ability of TACN-derivatives to form highly stable complexes with copper(II) is greatly influenced by the number and type of substituents on the macrocyclic ring. The formed copper(II) complexes show a broad variability in their thermodynamic stability and kinetic inertness, varying in structure from square-pyramidal to distorted octahedral. TACN-based BFCAs have also been used for indirect radiolabelling of biomolecules, rendering them suitable for imaging and therapy.

Technology Process of 1,4,7-Triazacyclononane

There total 12 articles about 1,4,7-Triazacyclononane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N,N',N''-tribenzyl-1,4,7-triazacyclononane (125262-43-3) → 1,4,7-triazacyclononane (4730-54-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 50 ℃; for 3h; under 760.051 Torr;

DOI:10.1002/ejoc.201800048

Reference yield: 91.0%

1,4,7-triazacyclononane trihydrochloride (58966-93-1) → 1,4,7-triazacyclononane (4730-54-5)

Guidance literature:

With sodium hydroxide; In water; toluene; Heating;

DOI:10.1039/b715254j

Reference yield: 86.0%

N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane (52667-89-7) → 1,4,7-triazacyclononane (4730-54-5)

Guidance literature:

N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane; With sulfuric acid; In water; at 140 ℃; for 20h;

With sodium hydroxide; In water; toluene; for 2h; Heating;

DOI:10.1002/1099-0682(200206)2002:6<1488::aid-ejic1488>3.0.co;2-#

upstream raw materials:

1,4,7-Triazacyclononane trihydrobromide

N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane

N,N',N''-tris(β-trimethylsilylethanesulfonyl)-1,4,7-triazacyclononane

1,4,7-triazacyclononane trihydrochloride

Downstream raw materials:

1,4,7-tris(pyridin-2-ylmethyl)-1,4,7-triazacyclononane

N,N',N''-tribenzyl-1,4,7-triazacyclononane

1-(5-benzamido-1-ethoxycarbonylpentyl)-4,7-diethoxycarbonyl-1,4,7-triazacyclononane

1,4-bis(5-benzamido-1-ethoxycarbonylpentyl)-7-ethoxycarbonyl-1,4,7-triazacyclononane

Refernces

• 1、 Bridonneau,Chamoreau,Gontard,Cantin,Von Bardeleben,Marvaud. "A high-nuclearity metal-cyanide cluster [Mo6Cu14] with photomagnetic properties". . p. 9412 - 9418. Retrieved 2016.
• 2、 -. "DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX". . . Retrieved 2021/03/19.
• 3、 -. "Synthesis method of 1, 4, 7-triazacyclononane". Paragraph 0010-0019. . Retrieved 2021/09/01.