1,4,8,11-Tetraazaundecane

1,4,8,11-Tetraazaundecane
Names
	Preferred IUPAC name N1,N3-Bis(2-aminoethyl)propane-1,3-diamine
	Other names 2,3,2-Tet, N,N′-bis(2-aminoethyl)-1,3-propanediamine
Identifiers
CAS Number	4741-99-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1742732
ChEBI	CHEBI:30348;
ChEMBL	ChEMBL1214193;
ChemSpider	70844;
ECHA InfoCard	100.022.958
EC Number	225-254-1;
Gmelin Reference	27228
PubChem CID	78479;
UNII	3J941O9333;
CompTox Dashboard (EPA)	DTXSID8063591 ;
	InChI InChI=1S/C7H20N4/c8-2-6-10-4-1-5-11-7-3-9/h10-11H,1-9H2 Key: UWMHHZFHBCYGCV-UHFFFAOYSA-N;
	SMILES C(CNCCN)CNCCN;
Properties
Chemical formula	C7H20N4
Molar mass	160.265 g·mol−1
Appearance	colorless oil
Density	0.9501
Boiling point	80–82 °C (176–180 °F; 353–355 K) 20 Torr
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,4,8,11-Tetraazaundecane, IUPAC name: N,N'-bis(2-aminoethyl)propane-1,3-diamine, is the organic compound with the formula (H₂NCH₂CH₂NHCH₂)₂CH₂. It is a tetramine, consisting of two primary amines and two secondary amines positioned symmetrically. Like many amines, this compound has a high affinity for carbon dioxide.^[1] The compound can be prepared by treatment of 1,3-dibromopropane with excess ethylenediamine.^[2]

The compound has been examined often as a ligand in coordination chemistry. It is tetradentate ligand similar to 1,4,7,10-tetraazadecane.^[3] By condensation of its nickel(II) complexes with formaldehyde, one can obtain a variety of macrocyclic ligands.^[4]

References

^ Puxty, Graeme; Rowland, Robert; Allport, Andrew; Yang, Qi; Bown, Mark; Burns, Robert; Maeder, Marcel; Attalla, Moetaz (2009). "Carbon Dioxide Postcombustion Capture: A Novel Screening Study of the Carbon Dioxide Absorption Performance of 76 Amines". Environmental Science & Technology. 43 (16): 6427–6433. Bibcode:2009EnST...43.6427P. doi:10.1021/es901376a. PMID 19746747.
^ Van Alphen, J. (1936). "On Aliphatic Polyamines III". Recueil des Travaux Chimiques des Pays-Bas. 55 (10): 835–840. doi:10.1002/recl.19360551004.
^ Bosnich, B.; Gillard, R. D.; McKenzie, E. D.; Webb, G. A. (1966). "Steric constraints imposed on facultative ligands. Complexes of triethylenetetramine and a homologue". Journal of the Chemical Society A: Inorganic, Physical, Theoretical: 1331. doi:10.1039/J19660001331.
^ De Blas, Andrés; De Santis, G.; Fabbrizzi, L.; Licchelli, Maurizio; Pallavicini, P. (1993). "Novel routes to functionalized cyclam-like macrocycles". Pure and Applied Chemistry. 65 (3): 455–459. doi:10.1351/pac199365030455.
^ Tsymbal, Liudmyla V.; Arion, Vladimir B.; Lampeka, Yaroslaw D. (2022). "Synthesis and crystal structure of trans -diaqua(1,4,8,11-tetraazaundecane)copper(II) isophthalate monohydrate". Acta Crystallographica Section E: Crystallographic Communications. 78 (8): 851–854. Bibcode:2022AcCrE..78..851T. doi:10.1107/S2056989022007538. PMC 9361364. PMID 35974816.