Jump to content

Tetramethylethylenediamine: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
A8v (talk | contribs)
1,194 edits
No edit summary
Line 71: Line 71:
| Function = amines
| Function = amines
| OtherFunctn = [[Triethylenetetramine]]
| OtherFunctn = [[Triethylenetetramine]]
| OtherCpds = {{unbulleted list|[[Tetraacetylethylenediamine]]|[[Ethylenediaminetetraacetic acid]]}}
| OtherCpds = {{unbulleted list|[[Tetraacetylethylenediamine]]|[[Ethylenediaminetetraacetic acid]]|[[Ethambutol]]}}
}}
}}
}}
}}

Revision as of 10:48, 17 December 2014

Tetramethylethylenediamine
Skeletal formula of tetramethylethylenediamine with some implicit hydrogens shown
Ball and stick model of tetramethylethylenediamine
Names
Other names
N,N,N′,N′-Tetramethylethane-1,2-diamine[1]
Identifiers
3D model (JSmol)
Abbreviations TMEDA, TEMED
1732991
ChEBI
ChemSpider
ECHA InfoCard 100.003.405 Edit this at Wikidata
EC Number
  • 203-744-6
2707
MeSH N,N,N',N'-tetramethylethylenediamine
RTECS number
  • KV7175000
UN number 2372
  • InChI=1S/C6H16N2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 ☒N
    Key: KWYHDKDOAIKMQN-UHFFFAOYSA-N ☒N
  • CN(C)CCN(C)C
Properties
C6H16N2
Molar mass 116.208 g·mol−1
Appearance Colorless liquid
Odor Ichtyal, ammoniacal
Density 0.7765 g mL−1 (at 20 °C)
Melting point −58.6 °C; −73.6 °F; 214.5 K
Boiling point 121.1 °C; 249.9 °F; 394.2 K
Miscible
Acidity (pKa) 8.97
Basicity (pKb) 5.85
1.4179
Structure
Hybridisation sp3 at C2, N5, C6, C10, C13, N16, C17, C21
0 D
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H225, H302, H314, H332
P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
4
1
Flash point 20 °C (68 °F; 293 K)
Explosive limits 0.98–9.08%
Lethal dose or concentration (LD, LC):
  • 5.39 g kg−1 (dermal, rabbit)
  • 268 mg kg−1 (oral, rat)
[2]
Related compounds
Supplementary data page
Tetramethylethylenediamine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 rotting 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]+.

TMEDA adduct of lithium bis(trimethylsilyl)amide. Notice that the diamine is a bidentate ligand.[5]

Other uses

TEMED 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 TEMED is a "traditional" range. TEMED can also be a component of Hypergolic propellants.

References

  1. ^ "N,N,N',N'-tetramethylethylenediamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Retrieved 30 June 2012.
  2. ^ "MSDS" (pdf).
  3. ^ a b c Haynes, R. K.; Vonwiller, S. C.; Luderer, M. R. (2006). "N,N,N',N'-Tetramethylethylenediamine". In Paquette, L. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X.rt064.pub2.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  4. ^ Morse, P. M.; Girolami, G. S. (1989). "Are d0 ML6 Complexes Always Octahedral? The X-ray Structure of Trigonal Prismatic [Li(tmed)]2[ZrMe6]". Journal of the American Chemical Society. 111 (11): 4114–4116. doi:10.1021/ja00193a061.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ K. W. Henderson, A. E. Dorigo, Qi-Long Liu, P. G. Williard "Effect of Polydentate Donor Molecules on Lithium Hexamethyldisilazide Aggregation:  An X-ray Crystallographic and a Combination Semiempirical PM3/Single Point ab Initio Theoretical Study" J. Am. Chem. Soc. 1997, volume 119, pp. 11855. doi:10.1021/ja971920t
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Tetramethylethylenediamine&oldid=638477992"