1,4,7-Triazacyclononane (HCID 188318)

Überblick

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

Namen und Bezeichner

Bevorzugter Name: 1,4,7-Triazacyclononane
IUPAC: 1,4,7-triazonane
Englischer Name: 1,4,7-Triazacyclononane
Summenformel: C6H15N3
Molmasse: 129.2

Namen und Synonyme

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

Weitere Namen anzeigen

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

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -1,9
Polarare Oberfläche (TPSA): 36,1 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 0
Schwere Atome: 9
Formalladung: 0
Komplexität: 45,1

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds

Physical DescriptionWhite crystals; [MSDSonline]

Physikochemische Eigenschaften

Schmelzpunkt: 42 · 42-45 °C (lit.)
Siedepunkt: 110 · 110-130 °C/7 mmHg (lit.)
Dichte: 0.9987 · 0.9987 (rough estimate)
Brechungsindex: 1.462 · 1.4620 (estimate)
Flammpunkt: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
Wasserlöslichkeit: Soluble in water
Löslichkeit: Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand: crystal
pka: 10.57 · 10.57±0.20(Predicted)
Farbe: white
BRN: 773877 · 773877
InChI: InChI=1S/C6H15N3/c1-2-8-5-6-9-4-3-7-1/h7-9H,1-6H2
InChIKey: ITWBWJFEJCHKSN-UHFFFAOYSA-N
SMILES: N1CCNCCNCC1

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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

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

Toxikologische Informationen

Adverse EffectsDermatotoxin - Skin burns.

Sicherheitsdaten

F: 3-10-34
wgk: 3
ridadr: UN 3259 8/PG 2
hs_code: 2933998090
risk_code: 34
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
packing_group: III

Chemie und Industrie

Anwendungen · 2 Einträge

Beschreibung1,4,7-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.

Verwenden1,4,7-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.

Darstellung · 1 Eintrag

synthetischeThe 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