Tmeda

Tetramethylethylenediamine


Identifiers
CAS number 110-18-9 YesY
PubChem 8037 YesY
ChemSpider 7746 N
EC number 203-744-6
UN number 2372
MeSH N,N,N',N'-tetramethylethylenediamine
ChEBI CHEBI:32850 YesY
RTECS number KV7175000
Beilstein Reference 1732991
Gmelin Reference 2707
Jmol-3D images Image 1
Properties
Molecular formula C6H16N2
Molar mass 116.20 g mol−1
Appearance Colorless liquid
Odor Ichtyal, ammoniacal
Density 0.7765 g mL−1 (at 20 °C)
Melting point

-59 °C, 214.5 K, -74 °F

Boiling point

121 °C, 394.2 K, 250 °F

Solubility in water Miscible
Acidity (pKa) 8.97
Basicity (pKb) 5.85
Refractive index (nD) 1.4179
Structure
Hybridisation sp3 at C2, N5, C6, C10, C13, N16, C17, C21
Dipole moment 0 D
Hazards
MSDS External MSDS
GHS pictograms
GHS signal word DANGER
GHS hazard statements H225, H302, H314, H332
GHS precautionary statements P210, P280, P305+351+338, P310
EU Index 612-103-00-3
EU classification C
R-phrases R11, R20/22, R34
S-phrases (S1/2), S16, S26, S36/37/39, S45
NFPA 704
4
2
1
Flash point 20 °C
Explosive limits 0.98–9.08%
LD50
  • 5.39 g kg−1 (dermal, rabbit)
  • 268 mg kg−1 (oral, rat)
[2]
Related compounds
Related amines Triethylenetetramine
Related compounds
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
 N (verify) (what is: YesY/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. It is a colourless liquid, although old samples often appear yellow. Its odor is remarkably similar to that of fish.[3]

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.[3] It converts n-butyllithium 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.[3] Many anionic organometallic complexes have been isolated as their [Li(tmeda)2]+ complexes.[4] 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. TMEDA can also be a component of Hypergolic propellants.

References

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