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1,4,7-Triazacyclononane trihydrochloride

1,4,7-Triazacyclononane trihydrochloride Struktur
58966-93-1
CAS-Nr.
58966-93-1
Englisch Name:
1,4,7-Triazacyclononane trihydrochloride
Synonyma:
152505;TACN,3HCl;1,4,7-TriazacyclononanetriHCl;1,4,7-triazacyclononane, 3HCl;1,4,7-triazonane-1,4,7-triium;1,4,7-triazonane hydrochloride;1,4,7-Triazacyclononane hydrochloride;1,4,7-TRIAZACYCLONONANE TRIHYDROCHLORIDE;Octahydro-1H-1,4,7-triazonine hydrochloride;1,4,7-Triazacyclononane trihydrochloride 97%
CBNumber:
CB1153163
Summenformel:
C6H18Cl3N3
Molgewicht:
238.59
MOL-Datei:
58966-93-1.mol

1,4,7-Triazacyclononane trihydrochloride Eigenschaften

Schmelzpunkt:
288 °C (dec.)(lit.)
storage temp. 
Inert atmosphere,Room Temperature
Aggregatzustand
Crystalline Powder
Farbe
Off-white to yellow
BRN 
5287631
InChIKey
HNPMVNQYFPWBKI-UHFFFAOYSA-N
CAS Datenbank
58966-93-1
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher C
R-S?tze: 34
S-S?tze: 26-36/37/39-45
RIDADR  UN 3261 8/PG 2
WGK Germany  3
3-9
HazardClass  8
PackingGroup  III
HS Code  29339900
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H314 Verursacht schwere Ver?tzungen der Haut und schwere Augensch?den. ?tzwirkung auf die Haut Kategorie 1B Achtung GHS hazard pictogramssrc="/GHS05.jpg" width="20" height="20" /> P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
Sicherheit
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P303+P361+P353 BEI BERüHRUNG MIT DER HAUT (oder dem Haar): Alle kontaminierten Kleidungsstücke sofort ausziehen. Haut mit Wasser abwaschen oder duschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.
P363 Kontaminierte Kleidung vor erneutem Tragen waschen.

1,4,7-Triazacyclononane trihydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R34:Verursacht Ver?tzungen.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).

Chemische Eigenschaften

1,4,7-Triazacyclononane trihydrochloride is a off-white to yellow crystalline powder that It is a chelate ring with six phosphate groups and six nitrogen atoms. It has been shown to behave as an irreversible oxidation catalyst for carboxylate and amine molecules. This molecule also has redox potentials in the range of -0.35 to -0.5 volts and can reversibly oxidize inorganic acids with strong electron-donating properties such as phosphoric acid, nitric acid, and sulfuric acid.

Verwenden

1,4,7-Triazacyclononane trihydrochloride is a possible reagent for compleximetric titrations with a high cation-binding selectivity. It is also used in the organic synthesis of ligands and compounds requiring a triazacyclononane group.

Application

1,4,7-Triazacyclononane trihydrochloride can be used as a reagent to prepare:
Nonadentate ligand, 1,4,7-tris[(6-carboxypyridin-2-yl)methyl]-1,4,7-triazacyclononane (H3tpatcn), which is used to prepare lanthanide complexes with high water solubility and rigid C3 symmetric structures.
Dansyl cryptands as fluorescent indicators via amination of (bromobenzyl)triazacycloalkane and oxadiamines.
[1,4,7-tri(3-butenyl)-1,4,7-triazacyclononane and 1,4,7-tri(2-propenyl)-1,4,7-triazacyclononane] by reacting with corresponding alkenyl halide.

Lager

This nitrogen crown ether analog, also known as octahydro-1h-1,4,7-triazonine trihydrochloride should be stored in a cool and dark place. Keep under inert gas and protect from moisture. 1,4,7-Triazacyclononane Trihydrochloride is known to be incompatible with oxidizing agents and should not be stored or handled in their vicinity.

synthetische

Synthesis of 1,4,7-Triazacyclononane trihydrochloride (tacn.3HCl)
A round bottom flask (1 L) was charged with 18M H2SO4 (450 mL) and 1,4,7-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane (4) (138.8 g, 0.234 mol) added in small portions (approximately 10 g every 5 min). The mixture was heated with stirring in a heat block for 3 days at 120°C. The resulting black solution was cooled to room temperature and added dropwise using a dropping funnel to a vigorously stirred mixture of cold absolute EtOH/Et2O (1.5 L/900 mL) cooled in an ice bath. An overhead stirrer was used to ensure efficient stirring. A sticky hygroscopic brown/grey precipitate formed, which was isolated quickly by vacuum filtration and immediately dissolved in de–ionised H2O (1 L). The mixture was heated for 2 h at 60°C. The mixture was then cooled to room temperature, filtered through Celite and the resulting solution concentrated to 250 mL under reduced pressure at 65°C. Conc. HCl (200 mL) was added followed by absolute EtOH until the solution became cloudy. The mixture was stored at 4°C overnight to promote precipitation. The white precipitate was collected by filtration and washed with ice cold absolute EtOH (3 x 50 mL), followed by Et2O (2 x 50 mL) to yield tacn.3HCl (5) as a white crystalline powder. Yield 44.9 g (80%).
mp. 268.1–270.0°C (Lit.4 mp. 280–281°C). 1H NMR (300 MHz, D2O) δH 3.48 (12H, s, CH2). 13C NMR (75 MHz, D2O) δC 43.1 (CH2). ESI–MS m/z [M + H]+ 130.1. The 1H and 13C NMR spectral data were consistent with literature data.
Using iSUSTAIN(TM) to validate the chemical attributes of different approaches to the synthesis of tacn and bridged bis(tacn) ligands

1,4,7-Triazacyclononane trihydrochloride Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


1,4,7-Triazacyclononane trihydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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58966-93-1()Verwandte Suche:


  • OCTAHYDRO-1H-1,4,7-TRIAZONINE TRIHYDROCHLORIDE
  • 1,4,7-TRIAZACYCLONONANE TRIHYDROCHLORIDE
  • 1,4,7-TRIAZACYCLONONANE TRIHYDROCHLORIDE 97+%
  • 1,4,7-TriazacyclononanetriHCl
  • 1,4,7-Triazacyclononane trihydrochloride 1,4,7-Triazacyclononane trihydrochloride
  • Octahydro-1H-1,4,7-triazonine hydrochloride
  • 1,4,7-Triazacyclononane trihydrochloride, 97% 500MG
  • 1H-1,4,7-Triazonine, octahydro-, trihydrochloride
  • 1H-1,4,7-Triazonine,octahydro-, hydrochloride (1:3)
  • 1,4,7-Triazacyclononane hydrochloride
  • 1,4,7-Triazacyclononane trihydrochloride 97%
  • 1,4,7-triazacyclononane, 3HCl
  • 152505
  • TACN,3HCl
  • 1,4,7-triazonane-1,4,7-triium
  • 1,4,7-triazonane hydrochloride
  • 58966-93-1
  • C6H15N3HCl
  • C6H18Cl3N3
  • C6H15N33HCl
  • Crown Ethers
  • Azacrown Ethers
  • Macrocycles for Host-Guest Chemistry
  • Chelation/Complexation Compounds
  • Synthetic Reagents
  • Chelation/Complexation Compounds
  • Crown Ethers
  • Synthetic Reagents
  • Azacrown Ethers
  • Crown Ethers
  • Functional Materials
  • Macrocycles for Host-Guest Chemistry
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