Tetramethylethylenediamine: Difference between revisions

| verifiedrevid = 408557560

| Name = Tetramethylethylenediamine

| ImageFile = Tmeda is.svg

| ImageSize = 200px

| ImageName = Tetramethylethylenediamine

| ImageFile1 = TMEDA-3D-balls.png

| ImageSize1 = 200px

| ImageName1 = Ball-and-stick model of the TMEDA molecule

| IUPACName =''N'',''N'',''N<nowiki>'</nowiki>'',''N<nowiki>'</nowiki>''-tetramethyl-<br />ethane-1,2-diamine

| OtherNames = TEMED; TMEDA; TMED; 1,2-Bis(dimethylamino)ethane

| Section1 = {{Chembox Identifiers

| SMILES = NC(C)(C)C(N)(C)C

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 109987

| PubChem = 123390

| InChI = 1/C6H16N2/c1-5(2,7)6(3,4)8/h7-8H2,1-4H3

| InChIKey = CGCVLTOGUMLHNP-UHFFFAOYAG

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H16N2/c1-5(2,7)6(3,4)8/h7-8H2,1-4H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CGCVLTOGUMLHNP-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| RTECS = KV7175000

}}

| Section2 = {{Chembox Properties

| Formula = C₆H₁₆N₂

| MolarMass = 116.24 g/mol

| Appearance = Colorless liquid

| Density = 0.78 g/cm³

| Solubility = infinite

| MeltingPtC = -55

| BoilingPtCL = 120

| BoilingPtCH = 122

| pKa = 8.97

| pKb = 5.85

| RefractIndex = 1.4179

}}

| Section3 = {{Chembox Structure

| Coordination = sp³ throughout

| Dipole = 0 [[Debye|D]]

}}

| Section7 = {{Chembox Hazards

| ExternalMSDS =

| MainHazards = Flammable,<br />Obnoxious odor

| NFPA-H = 2

| NFPA-F = 4

| NFPA-R = 1

| FlashPt = {{convert|10|C|F}}

| RPhrases = {{R11}} {{R20/22}} {{R34}}

| SPhrases = {{S16}} {{S26}} {{S36/37/39}} {{S45}}

}}

| 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 from [[ethylenediamine]] by replacement of the four N-H groups with four N-[[methyl]] groups. Its odor is remarkably similar to that of fish.<ref name=EROS>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}}.</ref>

==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.<ref name=EROS/> 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-alkyl[[pyrrole]]s, and [[ferrocene]].<ref name=EROS /> Many anionic organometallic complexes have been isolated as their [Li(tmeda)₂]⁺ complexes.<ref>{{cite journal | author = Morse, P. M.; Girolami, G. S. | title = Are d⁰ ML₆ Complexes Always Octahedral? The X-ray Structure of Trigonal Prismatic [Li(tmed)]₂[ZrMe₆] | journal = J. Am. Chem. Soc.| year = 1989 | volume = 111 | pages = 4114–5 | doi = 10.1021/ja00193a061}}</ref> 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 gel]]s, 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.

== Safety ==

TEMED is highly flammable. Harmful by inhalation and if swallowed. Causes burns. It is better to apply under the hood.

[[Category:Amines]]

[[de:Tetramethylethylendiamin]]

[[fr:Tétra-méthyl-éthylènediamine]]

[[it:Tetrametiletilendiammina]]

[[nl:Tetramethylethyleendiamine]]

[[ja:テトラメチルエチレンジアミン]]

[[pl:N,N,N',N'-Tetrametyloetylenodiamina]]

[[zh:四甲基乙二胺]]