1,4,7-Triazacyclononane

1,4,7-Triazacyclononane Basic information
Product Name:1,4,7-Triazacyclononane
Synonyms:1,4,7-TRIAZACYCLONONANE;OCTAHYDRO-1H-1,4,7-TRIAZONINE;Octahydro-1H-1,4,7-triazonine, Triethylenetriamine;1,4,7-Triazacyclonomane;TRIETHYLENETRIAMINE;Triazacyclononanewhitextl;1,4,7-Triazacyclononane,97%;1,4,7-triazonane
CAS:4730-54-5
MF:C6H15N3
MW:129.2
EINECS:637-157-5
Product Categories:Achiral Nitrogen;Cy-N;organic amine
Mol File:4730-54-5.mol
1,4,7-Triazacyclononane Structure
1,4,7-Triazacyclononane Chemical Properties
Melting point 42-45 °C (lit.)
Boiling point 110-130 °C/7 mmHg (lit.)
density 0.9987 (rough estimate)
refractive index 1.4620 (estimate)
Fp >230 °F
storage temp. 2-8°C
Water Solubility Soluble in water
solubility Chloroform (Slightly), Methanol (Slightly)
pka10.57±0.20(Predicted)
form crystal
color white
BRN 773877
InChIKeyITWBWJFEJCHKSN-UHFFFAOYSA-N
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 26-36/37/39-45
RIDADR UN 3259 8/PG 2
WGK Germany 3
3-10-34
HazardClass 8
PackingGroup III
HS Code 2933998090
MSDS Information
ProviderLanguage
SigmaAldrich English
1,4,7-Triazacyclononane Usage And Synthesis
Description1,4,7-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.
Chemical PropertiesWhite - light yellow solid
UsesStarting material for the synthesis of 1,4,7-trifunctionalized derivatives which have applications in metal complexation.
Uses1,4,7-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.
ApplicationStarting material for the synthesis of 1,4,7-trifunctionalized derivatives which have applications in metal complexation.
Possible reagent for compleximetric titrations with high cation-binding selectivity.
PreparationThe ligand is prepared from diethylene triamine as follows by macrocyclization using ethyleneglycol ditosylate.
H2NCH2CH2NHCH2CH2NH2 + 3 TsCl → Ts(H)NCH2CH2N(Ts)CH2CHH2N(H)Ts + 3 HCl Ts(H)NCH2CH2N(Ts)CH2CH2N(H)Ts + 2 NaOEt → Ts(Na)NCH2CH2N(Ts)CH2CH2N(Na)Ts Ts(Na)NCHH2CH2N(Ts)CH2CH2N(Na)Ts + TsOCH2CH2OTs + → [(CH2CH2N(Ts)]3 + 2 NaOTs [(CH2CH2N(Ts)]3 + 3 H2O → [CH2CH2NH]3 + 3 HOTs
DefinitionChEBI: 1,4,7-triazonane is a saturated organic heteromonocyclic parent, a crown amine and an azacycloalkane.
1,4,7-Triazacyclononane Preparation Products And Raw materials
Preparation Products6BH-2A,4A,6A-TRIAZACYCLOPENTA[CD]PENTALENE, HEXAHYDRO- (9CI)
N,N,N',N',N'',N''-Hexamethyl-1,4,7-triazacyclononane-1,4,7-tri(acetamide) 1,4,7-Triazacyclononane trihydrochloride 1,4,7-triazacyclononane-N,N',N''-tris(methylenephosphonate monoethyl ester) N',N',N'-tris(2-methyl-2-mercaptopropyl)-1,4,7-triazacyclononane 3-Benzyl-6,9-dimethyl-3,6,9-triazacyclononane,1-Benzyl-4,7-dimethyl-1,4,7-triazacyclononane,1,4-Dimethyl-7-benzyl-1,4,7-triazacyclononane CYCLEN-GLYOXAL 1,4,7-triazacyclononane-1,4,7-tris(methylene methylphosphinic acid) (1,4,7-trimethyl-1,4,7-triazacyclononane)iron(III) N,N,N',N',N'',N''-Hexamethyl-1,4,7-triazacyclononane-1,4,7-tripropionamide 1,4,7-Triazacyclononane 1,4,7-TRIMETHYL-1,4,7-TRIAZACYCLONONANE 1,7-Dimethyl-4-[2-(ethylamino)ethyl]-1,4,7-triazacyclononane 1,4-Dioxane N-NONANE 1-acetato-1,4,7-triazacyclononane N,N',N''-tris(2-methyl-(2-mercaptopropyl))-1,4,7-triazacyclononane-pertechnetate HEXABENZILISOVYURTSITAN DODECAHYDRO-3H,7BH-2A,5,5B,7A,10,10B-HEXAAZACYCLOPENTA[HI]ACEANTHRYLENE

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