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N,N,N',N'-Tetramethylethylenediamine is used with ammonium persulfate to catalyze the polymerization of acrylamide and bis-acrylamide to get polyacrylamide gels. It is also used for the separation of proteins or nucleic acids. Further, it is employed as a ligand for metal ions like zinc and copper. It is actively involved in the formation of anionic organometallic complex.
Widely used complexing agent in lithiation reactions, often giving enhanced reactivity in otherwise difficult metallations: J. Am. Chem. Soc., 92, 4664 (1970). Subsequent work by Collum and others indicated that the situation may be much less straightforward than was previously thought, but the effect of TMEDA is likely to be most pronounced in the absence of strong donor solvents such as THF. For a discussion of the factors involved, see: Acc. Chem. Res., 25, 448 (1992). Under some conditions also, TMEDA itself may undergo lithiation: Organometallics, 13, 5173 (1994).
Used in combination with alkyllithiums in the ortho-metallation of aromatics; see, e.g.: Org. Synth. Coll., 6, 478 (1988); Org. Synth. Coll., 9, 559 (1998). For discussion of the dramatic acceleration of the rate of ortho-lithiation of anisole in the presence of TMEDA, effective also in sub-stoichiometric amounts, see: Tetrahedron Lett., 35, 385 (1994). See also Tetrahedron Lett., 35, 401 (1994), J. Org. Chem., 62, 3024 (1997) for further discussion of the role of TMEDA in ortho-metallation.
The oxidative coupling of terminal acetylenes to diynes, by O2 in the presence of CuCl, is improved by addition of TMEDA as a complexing agent: J. Org. Chem., 27, 3320 (1962). For example and discussion, see: Org. Synth. Coll., 8, 63 (1993):
In catalytic amounts, produces up to a 20-fold increase in reaction rate in aqueous Michael additions catalyzed by ytterbium triflate: J. Org. Chem., 71, 352 (2006).
Zhao, N.; Liu, L.; Wang, F.; Li, J.; Zhang, W. Copper/N, N, N', N'-Tetramethylethylenediamine-Catalyzed Synthesis of N-Substituted Benzoheterocycles via C-S Cross-Coupling at Ambient Temperature in Water. Adv. Synth. Catal. 2014, 356 (11-12), 2575-2579.
Cheng, X.; Zhang, Y.; Deb, S.; Minitti, M. P.; Gao, Y.; Jónsson, H.; Weber, P. M. Ultrafast structural dynamics in Rydberg excited N, N, N', N'-tetramethylethylenediamine: conformation dependent electron lone pair interaction and charge delocalization. Chem. Sci. 2014, 5 (11), 4394-4403.
Gefahrenhinweise (EU): H225-H302-H332-H314
Highly flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes severe skin burns and eye damage.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.