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110-18-9 - N,N,N',N'-Tetramethylethylenediamine, 99% - 1,2-Bis(dimethylamino)ethane - TMEDA - A12536 - Alfa Aesar

A12536 N,N,N',N'-Tetramethylethylenediamine, 99%

Codice CAS
110-18-9
Sinonimi
1,2-Bis(dimethylamino)ethane
TMEDA

Dimensioni Prezzo ($) Quantità Disponibilità
100ml 27,60
500ml 74,30
2500ml 301,00
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N,N,N',N'-Tetramethylethylenediamine, 99%

MDL
MFCD00008335
EINECS
203-744-6

Proprietà chimiche

Formula
C6H16N2
Peso formula
116.21
Punto di fusione
-55°
Punto di ebollizione
120-122°
Punto di infiammabilità
18°(62°F)
Densità
0.775
Indice di rifrazione
1.4180
Sensibilità
Air & Moisture Sensitive
Solubilità
Miscible with water.

Applicazioni

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.

Note

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents, carbon dioxide and copper.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225-H302-H332-H314

Highly flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes severe skin burns and eye damage.

Dichiarazioni precauzionali: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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.

Altri riferimenti

Beilstein
1732991
Classe di rischio
3
Gruppo di imballaggio
II
Codice tariffe armonizzato
2921.29
TSCA
Yes
RTECS
KV7175000

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