CAS 4730-54-5 1,4,7-Triazacyclononane (HCID 188318)

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Basic information

CAS: 4730-54-5
Standard SMILES: C1CNCCNCCN1
InChIKey: ITWBWJFEJCHKSN-UHFFFAOYSA-N
Molecular formula: C6H15N3
Average molar mass: 129.2 g/mol
Monoisotopic mass: 129.12659748

Overview

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

Names & identifiers

Preferred name: 1,4,7-Triazacyclononane
IUPAC: 1,4,7-triazonane
English name: 1,4,7-Triazacyclononane
Molecular formula: C6H15N3
Molecular weight: 129.2

Names & synonyms

1,4,7-Triazacyclononane4730-54-51H-1,4,7-Triazonine, octahydro-2UIF93C5H3DTXSID50197095NSC-681101RefChem:415824DTXCID60119586637-157-51,4,7-TriazonanetacnOctahydro-1H-1,4,7-triazonine

Show more names

157715Triazacyclononane1,4,8-Triazacyclononane1,4,7-Triazacyclonomane1,4,7-triazacycloheptaneTriazacyclononanewhitextl

MFCD00012358Triethylenetriamine[9]aneN3SCHEMBL132539CHEBI:374051,4,7-Triazacyclononane, 95%NSC681101EN300-213777

Database identifiers

CAS: 4730-54-5
PubChem CID: 188318
DTXSID: DTXSID50197095
ChEMBL: CHEMBL1650628
ChEBI: CHEBI:37405
UNII: 2UIF93C5H3
EC Number: 637-157-5
Nikkaji: J351.553B

Properties

Computed structural properties

XLogP: -1.9
Topological polar surface area: 36.1 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 9
Formal charge: 0
Complexity: 45.1

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds

Physical DescriptionWhite crystals; [MSDSonline]

Physicochemical properties

Melting point: 42 · 42-45 °C (lit.)
Boiling point: 110 · 110-130 °C/7 mmHg (lit.)
Density: 0.9987 · 0.9987 (rough estimate)
refractive index: 1.462 · 1.4620 (estimate)
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
Water Solubility: Soluble in water
solubility: Chloroform (Slightly), Methanol (Slightly)
form: crystal
pka: 10.57 · 10.57±0.20(Predicted)
color: white
BRN

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazards SummaryCorrosive--causes burns; Inhalation of high concentration may cause chemical pneumonitis; [MSDSonline]

Hazard Classes and CategoriesSkin Corr. 1B (100%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

F: 3-10-34
wgk: 3
ridadr: UN 3259 8/PG 2
hs_code: 2933998090
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
packing_group: III
Hazard statements: H314
Precautionary statements

Chemistry & industry

Applications · 3 items

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.

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.

Preparation methods · 1 item

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