1,4,7-Trimethyl-1,4,7-triazacyclononane

1,4,7-Trimethyl-1,4,7-triazacyclononane
Names
	Other names Me3TACN; Trimethyltriazacyclononane; N,N′,N′′-Trimethyl-1,4,7-triazacyclononane;
Identifiers
CAS Number	96556-05-7;
3D model (JSmol)	Interactive image;
ChemSpider	476078;
ECHA InfoCard	100.119.348
EC Number	619-228-2;
PubChem CID	546957;
CompTox Dashboard (EPA)	DTXSID80338151 ;
	InChI InChI=1S/C9H21N3/c1-10-4-6-11(2)8-9-12(3)7-5-10/h4-9H2,1-3H3 Key: WLDGDTPNAKWAIR-UHFFFAOYSA-N;
	SMILES CN1CCN(CCN(CC1)C)C;
Properties
Chemical formula	C9H21N3
Molar mass	171.288 g·mol−1
Appearance	Colorless oil
Boiling point	207.8 °C (406.0 °F; 480.9 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H314
GHS precautionary statements	P260, P264, P270, P280, P301+312, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P330, 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

1,4,7-Trimethyl-1,4,7-triazacyclononane is the heterocyclic compound with the formula (CH₂CH₂NCH₃)₃. This colorless liquid is the N-methylated derivative of triazacyclononane (TACN), a face-capping tridentate ligand that is popular in coordination chemistry.

Although TACN is known for forming 2:1 "sandwich" complexes with many metal ions,[1] corresponding 2:1 complexes of Me₃TACN are only known for Ag⁺,[2] Na⁺,[3] and K⁺.[4] This effect is mainly due to the greater bulk of Me₃TACN, which requires ions with a larger ionic radius to accommodate two ligands.

Several related derivatives have been prepared with diverse substituents on nitrogen.[5][6]

Generic octahedral metal complex of Me₃TACN.

References

Weighardt, Karl (1988). "1,4,7-Triazacyclononane and N,N',N"-Trimethyl-1,4,7-triazacyclononane - Two Versatile Macrocycles for the Synthesis of Monomeric and Oligomeric Metal Complexes". Pure and Applied Chemistry. 60 (4): 509–16. doi:10.1351/pac198860040509. S2CID 96871622.
Stockheim, Claudia; Wieghardt, Karl; Nuber, Bernhard; Weiss, Johannes; Flöurke, Ulrich; Haupt, Hans-Jürgen (1991). "Co-ordination chemistry of 1,4,7-triazacyclononane (L) and its N-methylated derivative (L′) with silver( I ) and mercury( II ). The crystal structures of [AgL′ 2 ]PF 6 and [AgL′(SCN)]". J. Chem. Soc., Dalton Trans. (6): 1487–1490. doi:10.1039/DT9910001487. ISSN 0300-9246.
Everett, Matthew; Jolleys, Andrew; Levason, William; Pugh, David; Reid, Gillian (2014). "Unexpected neutral aza-macrocycle complexes of sodium". Chemical Communications. 50 (44): 5843–6. doi:10.1039/c4cc01407c. ISSN 1359-7345. PMID 24759888.
Dyke, John; Levason, William; Light, Mark E.; Pugh, David; Reid, Gillian; Bhakhoa, Hanusha; Ramasami, Ponnadurai; Rhyman, Lydia (2015). "Aza-macrocyclic complexes of the Group 1 cations – synthesis, structures and density functional theory study". Dalton Trans. 44 (31): 13853–13866. doi:10.1039/C5DT01865J. ISSN 1477-9226. PMID 26115444.
Jason A. Halfen; William B. Tolman (1998). "C₂‐Symmetric 1,4‐Diisopropyl‐7‐R‐1,4,7‐Triazacyclononanes". Inorganic Syntheses. 32: 75–81. doi:10.1002/9780470132630.ch12. ISBN 9780470132630.
Baker, M. V.; Brown, D. H.; Skelton, B. W.; White, A. H. (2002). "An Investigation into Alkenyl-Functionalized 1,4,7-Triazacyclononanes: Synthesis, Metal Complexation, and Attempted Olefin Metathesis". Australian Journal of Chemistry. 55 (10): 655. doi:10.1071/CH02063.

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[1] Weighardt, Karl (1988). "1,4,7-Triazacyclononane and N,N',N"-Trimethyl-1,4,7-triazacyclononane - Two Versatile Macrocycles for the Synthesis of Monomeric and Oligomeric Metal Complexes". Pure and Applied Chemistry. 60 (4): 509–16. doi:10.1351/pac198860040509. S2CID 96871622.

[2] Stockheim, Claudia; Wieghardt, Karl; Nuber, Bernhard; Weiss, Johannes; Flöurke, Ulrich; Haupt, Hans-Jürgen (1991). "Co-ordination chemistry of 1,4,7-triazacyclononane (L) and its N-methylated derivative (L′) with silver( I ) and mercury( II ). The crystal structures of [AgL′ 2 ]PF 6 and [AgL′(SCN)]". J. Chem. Soc., Dalton Trans. (6): 1487–1490. doi:10.1039/DT9910001487. ISSN 0300-9246.

[3] Everett, Matthew; Jolleys, Andrew; Levason, William; Pugh, David; Reid, Gillian (2014). "Unexpected neutral aza-macrocycle complexes of sodium". Chemical Communications. 50 (44): 5843–6. doi:10.1039/c4cc01407c. ISSN 1359-7345. PMID 24759888.

[4] Dyke, John; Levason, William; Light, Mark E.; Pugh, David; Reid, Gillian; Bhakhoa, Hanusha; Ramasami, Ponnadurai; Rhyman, Lydia (2015). "Aza-macrocyclic complexes of the Group 1 cations – synthesis, structures and density functional theory study". Dalton Trans. 44 (31): 13853–13866. doi:10.1039/C5DT01865J. ISSN 1477-9226. PMID 26115444.

[5] Jason A. Halfen; William B. Tolman (1998). "C₂‐Symmetric 1,4‐Diisopropyl‐7‐R‐1,4,7‐Triazacyclononanes". Inorganic Syntheses. 32: 75–81. doi:10.1002/9780470132630.ch12. ISBN 9780470132630.

[6] Baker, M. V.; Brown, D. H.; Skelton, B. W.; White, A. H. (2002). "An Investigation into Alkenyl-Functionalized 1,4,7-Triazacyclononanes: Synthesis, Metal Complexation, and Attempted Olefin Metathesis". Australian Journal of Chemistry. 55 (10): 655. doi:10.1071/CH02063.