Tetramethylethylenediamine
| Tetramethylethylenediamine | |
|---|---|
| Tetramethylethylenediamine | |
| Ball-and-stick model of the TMEDA molecule | |
| N,N,N',N'-tetramethyl- ethane-1,2-diamine | |
| Other names TEMED TMEDA TMED 1,2-bis(dimethylamino)- ethane | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 110-18-9 
|
| RTECS number | KV7175000 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C6H16N2 |
| Molar mass | 116.24 g/mol |
| Appearance | colorless liquid |
| Density | 0.78 g/cm3, liquid |
| Melting point |
-55 °C (218 K) |
| Boiling point |
120-122 °C (393-395 K) |
| Solubility in water | infinite |
| Acidity (pKa) | 8.97 |
| Basicity (pKb) | 5.85 |
| Refractive index (nD) | 1.4179 |
| style="background: #F8EABA; text-align: center;" colspan="2" | Structure | |
| sp3 throughout | |
| Dipole moment | 0 D |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| R-phrases | 11-20/22-34 |
| S-phrases | 16-26-36/37/39-45 |
| NFPA 704 | |
| Flash point | 50 °F |
| style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds | |
| Related amines | ethylene diamine, PMDTA, trimethyltriazacyclononane |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Tetramethylethylenediamine (TMEDA or TEMED) is a chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived from ethylenediamine by replacement of the four N-H groups with four N-methyl groups. It has an odor that smells remarkably similar to fish.[1]
As a reagent in organic and inorganic synthesis
TMEDA is widely employed as a ligand for metal ions. It forms stable complexes with many metal halides, e.g. zinc chloride and copper(I) iodide, giving complexes that are soluble in organic solvents. In such complexes, TMEDA serves as a bidentate ligand.
TMEDA has an affinity for lithium ions.[1] It converts butyl lithium into a cluster of higher reactivity than the hexamer. BuLi/TMEDA is able to metallate or even doubly metallate many substrates including benzene, furan, thiophene, N-alkylpyrroles, and ferrocene.[1] Many anionic organometallic complexes have been isolated as their [Li(tmeda)2]+ complexes.[2] In such complexes [Li(tmeda)2]+ behaves like a quaternary ammonium salt, such as [NEt4]+.
Other uses
Tetramethylethylenediamine is used with ammonium persulfate to catalyze the polymerization of acrylamide when making polyacrylamide gels, used in gel electrophoresis, for the separation of proteins or nucleic acids. Although the amounts used in this technique may vary from method to method, 0.1-0.2% v/v TMEDA is a "traditional" range.
References
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zh:四甲基乙二胺- ↑ 1.0 1.1 1.2 Haynes, R. K.; Vonwiller, S. C. "N,N,N',N'-Tetramethylethylenediamine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi: 10.1002/047084289.
- ↑ Morse, P. M.; Girolami, G. S. (1989). "Are d0 ML6 Complexes Always Octahedral? The X-ray Structure of Trigonal Prismatic [Li(tmed)]2[ZrMe6]". J. Am. Chem. Soc. 111: 4114–5. doi:10.1021/ja00193a061.
