Tris(2-(2-methoxyethoxy)ethyl)amine

Tris(2-(2-methoxyethoxy)ethyl)amine
Names
	Other names TDA-1, Tris(3,6-dioxaheptyl)amine
Identifiers
CAS Number	70384-51-9;
3D model (JSmol)	Interactive image;
ChemSpider	100755;
ECHA InfoCard	100.067.787
EC Number	274-590-5;
PubChem CID	112414;
CompTox Dashboard (EPA)	DTXSID5072064 ;
	InChI InChI=1S/C15H33NO6/c1-17-10-13-20-7-4-16(5-8-21-14-11-18-2)6-9-22-15-12-19-3/h4-15H2,1-3H3 Key: XGLVDUUYFKXKPL-UHFFFAOYSA-N;
	SMILES COCCOCCN(CCOCCOC)CCOCCOC;
Properties
Chemical formula	C15H33NO6
Molar mass	323.430 g·mol−1
Appearance	colorless oily liquid
Boiling point	171 °C (340 °F; 444 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H314
Precautionary statements	P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, 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

Tris(2-(2-methoxyethoxy)ethyl)amine is the organic compound with the formula N(CH₂CH₂OCH₂CH₂OCH₃)₃. It is an amine and a polyether that can complex various metal ions. The compound is colorless, although samples can appear yellow.

Structure of K⁺ bound to TDA-1.^[1] Color code: red = O, blue = N, turquoise = K.

Tris(2-(2-methoxyethoxy)ethyl)amine used in phase transfer catalysis (PTC).^[2] For PTC, it has been described as superior to 18-crown-6.^[3]

References

^ Mague, J. T. (1998). "Luminescent Cu^I Clusters. Bis({tris[2-(2-methoxyethoxy)ethyl]amine}potassium) Hexaiodotetracuprate(I)". Acta Crystallographica Section C Crystal Structure Communications. 54 (4): IUC9800010. doi:10.1107/S0108270198099776.
^ Marc Halpern "Phase-Transfer Catalysis" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_293
^ Bose, Ajay K.; Mangiaracina, Pietro (1987). "Tris(3,6-dioxaheptyl)amine: A Superior Complexing Agent for Dissolving Metal Reactions". Tetrahedron Letters. 28 (22): 2503–2506. doi:10.1016/S0040-4039(00)95452-2.

[1] Mague, J. T. (1998). "Luminescent Cu^I Clusters. Bis({tris[2-(2-methoxyethoxy)ethyl]amine}potassium) Hexaiodotetracuprate(I)". Acta Crystallographica Section C Crystal Structure Communications. 54 (4): IUC9800010. doi:10.1107/S0108270198099776.

[Ullmann-2] Marc Halpern "Phase-Transfer Catalysis" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_293

[3] Bose, Ajay K.; Mangiaracina, Pietro (1987). "Tris(3,6-dioxaheptyl)amine: A Superior Complexing Agent for Dissolving Metal Reactions". Tetrahedron Letters. 28 (22): 2503–2506. doi:10.1016/S0040-4039(00)95452-2.

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