1,4,7-Triazacyclononane

Synonym(s):Octahydro-1H-1,4,7-triazonine;Triethylenetriamine

CAS NO.：4730-54-5
Empirical Formula: C6H15N3
Molecular Weight: 129.2
MDL number: MFCD00012358
EINECS: 637-157-5
SAFETY DATA SHEET (SDS)
Update Date: 2025-07-24 18:13:44

What is 1,4,7-Triazacyclononane?

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.

Chemical properties

White - light yellow solid

The Uses of 1,4,7-Triazacyclononane

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.

The Uses of 1,4,7-Triazacyclononane

Starting material for the synthesis of 1,4,7-trifunctionalized derivatives which have applications in metal complexation.

What are the applications of Application

1,4,7-Triazacyclononane is a possible reagent for compleximetric titrations with high cation-binding selectivity

Preparation

The 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

What are the applications of Application

Starting 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.

Definition

ChEBI: 1,4,7-triazonane is a saturated organic heteromonocyclic parent, a crown amine and an azacycloalkane.

Properties of 1,4,7-Triazacyclononane

Melting point:	42-45 °C (lit.)
Boiling point:	110-130 °C/7 mmHg (lit.)
Density	0.9987 (rough estimate)
refractive index	1.4620 (estimate)
Flash point:	>230 °F
storage temp.	2-8°C
Water Solubility	Soluble in water
solubility	Chloroform (Slightly), Methanol (Slightly)
pka	10.57±0.20(Predicted)
form	crystal
color	white
BRN	773877

Safety information for 1,4,7-Triazacyclononane

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05
GHS Hazard Statements	H314:Skin corrosion/irritation
Precautionary Statement Codes	P260:Do not breathe dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.