Tetramethylethylenediamine

Tetramethylethylenediamine
Identifiers
CAS number 110-18-9 Y
PubChem 123390
ChemSpider 109987 Y
RTECS number KV7175000
Jmol-3D images Image 1
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
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
 Y (verify) (what is: Y/N?)
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. Its odor is remarkably similar to that of 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

  1. ^ a b c 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.
  2. ^ 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 (11): 4114–5. doi:10.1021/ja00193a061.