| Tetramethylethylenediamine | |
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N,N,N',N'-tetramethyl- |
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Other names
TEMED; TMEDA; TMED; 1,2-Bis(dimethylamino)ethane |
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| Identifiers | |
| CAS number | 110-18-9 |
| PubChem | 123390 |
| ChemSpider | 109987 |
| RTECS number | KV7175000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H16N2 |
| Molar mass | 116.24 g/mol |
| Appearance | Colorless liquid |
| Density | 0.78 g/cm3 |
| Melting point |
-55 °C, 218 K, -67 °F |
| Boiling point |
120-122 °C, 393-395 K, 248-252 °F |
| Solubility in water | infinite |
| Acidity (pKa) | 8.97 |
| Basicity (pKb) | 5.85 |
| Refractive index (nD) | 1.4179 |
| Structure | |
| Coordination geometry |
sp3 throughout |
| Dipole moment | 0 D |
| Hazards | |
| MSDS | External MSDS |
| R-phrases | R11 R20/22 R34 |
| S-phrases | S16 S26 S36/37/39 S45 |
| Main hazards | Flammable, Obnoxious odor |
| NFPA 704 |
4
2
1
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| Flash point | 10 °C (50 °F) |
| Related compounds | |
| Related amines | Ethylene diamine, PMDTA, Trimethyltriazacyclononane |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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. Its odor is remarkably similar to that of fish.[1]
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]+.
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.