1,4,8,11-Tetraazacyclotetradecan

Bezeichnung:1,4,8,11-Tetraazacyclotetradecan

CAS-Nr295-37-4

Englisch Name:1,4,8,11-Tetraazacyclotetradecane

CBNumberCB3136889

SummenformelC10H24N4

Molgewicht200.32

MOL-Datei295-37-4.mol

Synonyma

1,4,8,11-Tetraazacyclotetradecan

1,4,8,11-Tetraazacyclotetradecan physikalisch-chemischer Eigenschaften

Schmelzpunkt	184-186 °C (lit.)
Siedepunkt	328.07°C (rough estimate)
Dichte	1.0203 (rough estimate)
Brechungsindex	1.5200 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	Dichloromethane, Methanol
Aggregatzustand	Fluffy Needle-Like Crystalline Powder
pka	10.90±0.20(Predicted)
Farbe	White
Wasserlöslichkeit	Soluble in water.
Sensitive	Air Sensitive
BRN	111811
InChI	InChI=1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2
InChIKey	MDAXKAUIABOHTD-UHFFFAOYSA-N
SMILES	N1CCCNCCNCCCNCC1
CAS Datenbank	295-37-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	XA5254800
F	3-9-34
HS Code	29339900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2
Toxizität	LD50 intraperitoneal in mouse: 371mg/kg

Gefahreninformationscode (GHS)

1,4,8,11-Tetraazacyclotetradecane Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
white fluffy needle-like crystalline powder
Verwenden
Reagent used in the preparation of Plerixafor derivatives.
Verwenden
1,4,8,11-Tetraazacyclotetradecane is used in the synthesis of molecules with electroactive cavities. It acts as a nitrogen crown ether analogue and as an antioxidant in rubber. It is also used in the preparation of plerixafor derivatives.
Verwenden
1,4,8,11-Tetraazacyclotetradecane is macrocyclic ligand that is used as an antioxidant in rubber and has been shown to suppress oxidation catalyzed by some metal ions.
Definition
ChEBI: 1,4,8,11-tetraazacyclotetradecane is a saturated organic heteromonocyclic parent, a crown amine and an azacycloalkane. It derives from a hydride of a cyclotetradecane.
Allgemeine Beschreibung
1,4,8,11-Tetraazacyclotetradecane is an azamacrocycle that forms more stable metal complexes as compared to open chain ligands.
Synthese

71089-74-2

295-37-4

The general procedure for the synthesis of 1,4,8,11-tetrakis[(4-methylphenyl)sulfonyl]-1,4,8,11-tetraazacyclotetradecane from 1,4,8,11-tetrakis(4-methylphenyl)sulfonyl]-1,4,8,11-tetraazacyclotetradecane is as follows: 1,4,8,11-tetra-tosyl-1,4,8,11-tetraazacyclotetradecane (13 mmol) was dissolved in 90% concentrated sulfuric acid, and the reaction was carried out at 100 °C The reaction was stirred for 48 hours at 100 °C. Upon completion of the reaction, the reaction mixture was cooled to 0°C. Subsequently, anhydrous ethanol (120 mL) and anhydrous ether (100 mL) were added dropwise to the reaction mixture to precipitate the solid product. The solid was collected by filtration and the filter cake was washed with a small amount of anhydrous ethanol and anhydrous ether, followed by vacuum drying. The resulting off-white solid was dissolved in 1 mol/L aqueous NaOH (90 mL) and extracted with chloroform (3 x 100 mL). The chloroform layers were combined and dried with anhydrous sodium sulfate overnight. Afterwards, the chloroform was removed by distillation under reduced pressure and the residue was vacuum dried to give a white solid product. Finally, the product was recrystallized from toluene to give 2.2 g of 1,4,8,11-tetraazacyclotetradecane in 85% yield. Mass spectral analysis of the product showed [M]+ = 200.3 m/e, 1H-NMR (400 MHz, CDCl3) δ ppm: 1.72 (t, 4H), 2.23 (s, 4H), 2.68 (s, 8H), 2.75 (t, 8H).
läuterung methode
Purify cyclam by recrystallisation from dioxane (white needles), and it sublimes above 120o. It has been distilled, b 132-140o/4-8mm. It forms complexes with metals and gives a sparingly soluble nitrate salt, m 205o(dec), which crystallises from H2O and is dried at 150o. [UV: Bosnich et al. Inorg Chem 4 1102 1963, van Alphen Recl Trav Chim Pays-Bas 56 343 1937, Beilstein 26 III/IV 1647.]
Einzelnachweise
[1] Patent: EP2163553, 2010, A1. Location in patent: Page/Page column 18-19
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 372 - 376
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 413 - 417
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 3, p. 346 - 349
[5] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 3, p. 401 - 404

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