- Tetramethylethylenediamine
Chembox new
Name = Tetramethylethylenediamine
ImageFile = temed.png
ImageName = Tetramethylethylenediamine
ImageFile1 = TMEDA-3D-balls.png
ImageName1 = Ball-and-stick model of the TMEDA molecule
IUPACName =N,N,N',N'-tetramethyl-
ethane-1,2-diamine
OtherNames = TEMED
TMEDA
TMED
1,2-bis(dimethylamino)-
ethane
Section1 = Chembox Identifiers
SMILES = CN(C)CCN(C)C
CASNo = 110-18-9
RTECS = KV7175000
Section2 = Chembox Properties
Formula = C6H16N2
MolarMass = 116.24 g/mol
Appearance = colorless liquid
Density = 0.78 g/cm3, liquid
Solubility = infinite
MeltingPt = -55 °C (218 K)
BoilingPt = 120-122 °C (393-395 K)
pKa = 8.97
pKb = 5.85
RefractIndex = 1.4179
Section3 = Chembox Structure
Coordination = sp3 throughout
Dipole = 0 D
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = flammable,
obnoxious odour
NFPA-H = 2 | Reactivity=1
NFPA-F = 4
NFPA-R =
FlashPt = 50 °F
RPhrases = 11-20/22-34
SPhrases = 16-26-36/37/39-45
Section8 = Chembox Related
Function =amine s
OtherFunctn =ethylene diamine ,PMDTA ,
trimethyltriazacyclononane Tetramethylethylenediamine (TMEDA or TEMED) is a
chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived fromethylenediamine by replacement of the four N-H groups with four N-methyl groups. It has a disagreeable fishy odour.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 andcopper(I) iodide , giving complexes that are soluble in organic solvents. In such complexes, TMEDA serves as a bidentate ligand.Perhaps TMEDA is most renowned for its affinity for
lithium ions. It convertsbutyl lithium into a cluster of higher reactivity than the hexamer. BuLi/TMEDA is able tometallate or even doubly metallate many substrates includingbenzene ,furan ,thiophene , N-alkylpyrrole s, andferrocene . [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.] Many anionic organometallic complexes have been isolated as their [Li(TMEDA)2] + complexes. [Morse, P. M.; Girolami, G. S. "Are d0 ML6 Complexes Always Octahedral? The X-ray Structure of Trigonal Prismatic [Li(tmed)] 2 [ZrMe6] ," Journal of the American Chemical Society 1989, volume 111, 4114-5.DOI|10.1021/ja00193a061] In such complexes [Li(TMEDA)2] + behaves like aquaternary ammonium salt, such as [NEt4] +.Other uses
Tetramethylethylenediamine is used with
ammonium persulfate to catalyze thepolymerization ofacrylamide when makingpolyacrylamide gel s, used ingel 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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