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1,4,7-Triazacyclononane

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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
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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)
Flash point:
>230 °F
storage temp. 
2-8°C
Water Solubility 
Soluble in water
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
crystal
pka
10.57±0.20(Predicted)
color 
white
BRN 
773877
InChIKey
ITWBWJFEJCHKSN-UHFFFAOYSA-N
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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

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1,4,7-Triazacyclononane Usage And Synthesis

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

Uses

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

Uses

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.

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.

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

Definition

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

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