1,4,7-Triazacyclononane, known as "TACN" which is pronounced "tack-en," is an aza-crown ether with the formula (C2H4NH)3.[1] 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 piperazine, C4H8(NH)2, and the cyclic tetramer 1,4,7,10-tetraazacyclododecane.
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Preferred IUPAC name
1,4,7-Triazonane | |
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3D model (JSmol)
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773877 | |
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.164.887 |
EC Number |
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2614 | |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C6H15N3 | |
Molar mass | 129.2046 g/mol |
Hazards | |
GHS labelling: | |
Danger | |
H314 | |
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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The ligand is prepared from diethylene triamine as follows by macrocyclization using ethyleneglycol ditosylate.[2]
TACN is a popular tridentate ligand. It is threefold symmetric and binds to one face of an octahedron of metalloids and transition metals. The (TACN)M unit is kinetically inert, allowing further synthetic transformations on the other coordination sites. A bulky analogue of TACN, is the N,N',N"-trimethylated analogue trimethyltriazacyclononane.