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Latest revision as of 23:59, 29 September 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,203 edits →Isomers: *Bis(dimethylamino)methane, {{chem2|Me2NCH2NMe2}} |
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{{chembox |
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| verifiedrevid = 408557560 |
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| verifiedrevid = 450059949 |
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| ImageFile = TMEDA.svg |
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| Name = Tetramethylethylenediamine |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Tmeda is.svg |
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| ImageSize = 200px |
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| ImageSize = 160 |
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| ImageName = Skeletal formula of tetramethylethylenediamine with some implicit hydrogens shown |
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| ImageName = Tetramethylethylenediamine |
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| ImageFile1 = TMEDA-3D-balls.png |
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| ImageFile1 = TMEDA-3D-balls.png |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| ImageSize1 = 200px |
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| ImageSize1 = 160 |
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| ImageName1 = Ball-and-stick model of the TMEDA molecule |
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| ImageName1 = Ball and stick model of tetramethylethylenediamine |
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| IUPACName =''N'',''N'',''N<nowiki>'</nowiki>'',''N<nowiki>'</nowiki>''-tetramethyl-<br />ethane-1,2-diamine |
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| PIN = ''N'',''N'',''N''′,''N''′-Tetramethylethane-1,2-diamine<ref>{{cite web|title=''N'',''N'',''N''′,''N''′-tetramethylethylenediamine – Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8037|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=30 June 2012|location=USA|date=16 September 2004}}</ref> |
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| OtherNames = TEMED; TMEDA; TMED; 1,2-Bis(dimethylamino)ethane |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = NC(C)(C)C(N)(C)C |
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| Abbreviations = TMEDA, TEMED |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 109987 |
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| PubChem = 123390 |
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| InChI = 1/C6H16N2/c1-5(2,7)6(3,4)8/h7-8H2,1-4H3 |
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| InChIKey = CGCVLTOGUMLHNP-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H16N2/c1-5(2,7)6(3,4)8/h7-8H2,1-4H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CGCVLTOGUMLHNP-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 110-18-9 |
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| CASNo = 110-18-9 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = KV7175000 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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}} |
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| UNII = K90JUB7941 |
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| Section2 = {{Chembox Properties |
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| PubChem = 8037 |
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| Formula = C<sub>6</sub>H<sub>16</sub>N<sub>2</sub> |
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| ChemSpiderID = 7746 |
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| MolarMass = 116.24 g/mol |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Appearance = Colorless liquid |
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| EINECS = 203-744-6 |
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| Density = 0.78 g/cm<sup>3</sup> |
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| UNNumber = 2372 |
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| Solubility = infinite |
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| MeSHName = N,N,N',N'-tetramethylethylenediamine |
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| MeltingPtC = -55 |
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| BoilingPtCL = 120 |
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| ChEBI = 32850 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| BoilingPtCH = 122 |
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| pKa = 8.97 |
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| RTECS = KV7175000 |
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| pKb = 5.85 |
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| Beilstein = 1732991 |
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| Gmelin = 2707 |
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| RefractIndex = 1.4179 |
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| SMILES = CN(C)CCN(C)C |
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}} |
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| StdInChI = 1S/C6H16N2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 |
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| Section3 = {{Chembox Structure |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Coordination = sp<sup>3</sup> throughout |
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| StdInChIKey = KWYHDKDOAIKMQN-UHFFFAOYSA-N |
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| Dipole = 0 ] |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section2={{Chembox Properties |
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| ExternalMSDS = |
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| C=6 | H=16 | N=2 |
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| MainHazards = Flammable,<br />Obnoxious odor |
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| Appearance = Colorless liquid |
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| NFPA-H = 2 |
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| Odor = Fishy, ammoniacal |
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| NFPA-F = 4 |
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| Density = 0.7765 g mL<sup>−1</sup> (at 20 °C) |
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| NFPA-R = 1 |
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| MeltingPtK = 214.5 |
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| FlashPt = {{convert|10|C|F}} |
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| BoilingPtK = 394.2 |
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| RPhrases = {{R11}} {{R20/22}} {{R34}} |
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| Solubility = Miscible |
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| SPhrases = {{S16}} {{S26}} {{S36/37/39}} {{S45}} |
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| pKa = 8.97 |
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}} |
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| pKb = 5.85 |
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| Section8 = {{Chembox Related |
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| RefractIndex = 1.4179 (20 °C)<ref name="CRC90_3_480">{{CRC90}}</ref> |
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| Function = ]s |
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}} |
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| OtherFunctn = ], ], ] |
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|Section4={{Chembox Hazards |
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}} |
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| GHSPictograms = {{gHS flame}} {{gHS corrosion}} {{gHS exclamation mark}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{h-phrases|225|302|314|332}} |
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| PPhrases = {{p-phrases|210|280|305+351+338|310}} |
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| NFPA-H = 2 |
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| NFPA-F = 4 |
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| NFPA-R = 1 |
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| FlashPtC = 20 |
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| ExploLimits = 0.98–9.08% |
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| LD50 = {{unbulleted list|5.39 g kg<sup>−1</sup> <small>(dermal, rabbit)</small>|268 mg kg<sup>−1</sup> <small>(oral, rat)</small>}}<ref>{{ cite web | url = http://www.wku.edu/msds/docs/2644.pdf | title = MSDS }}{{Dead link|date=June 2018 |bot=InternetArchiveBot |fix-attempted=no }}</ref> |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = amines |
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| OtherFunction = ] |
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| OtherCompounds = {{unbulleted list|]|]|]}} |
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'''Tetramethylethylenediamine''' ('''TMEDA''' or '''TEMED''') is a ] with the formula (CH<sub>3</sub>)<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub>. This species is derived from ] by replacement of the four N-H groups with four N-] 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> |
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'''Tetramethylethylenediamine''' ('''TMEDA''' or '''TEMED''') is a ] with the formula (CH<sub>3</sub>)<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub>. This species is derived from ] by replacement of the four ] ]s with four ] groups. It is a colorless liquid, although old samples often appear yellow. Its odor is similar to that of rotting fish.<ref name=EROS>{{cite encyclopedia |last1=Haynes |first1=R. K. |last2=Vonwiller |first2=S. C. |last3=Luderer |first3=M. R. | title = ''N'',''N'',''N''′,''N''′-Tetramethylethylenediamine | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | editor-last = Paquette |editor-first=L. | year = 2006 | publisher = J. Wiley & Sons | location = New York | doi = 10.1002/047084289X.rt064.pub2 |chapter=N,N,N′,N′-Tetramethylethylenediamine |isbn=0471936235}}</ref> |
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==As a reagent in organic and inorganic synthesis== |
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==As a reagent in synthesis== |
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TMEDA is widely employed as a ] for metal ions. It forms stable complexes with many metal halides, e.g. ] and ], giving complexes that are soluble in organic solvents. In such complexes, TMEDA serves as a bidentate ligand. |
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TMEDA is widely employed as a ] for metal ions. It forms stable complexes with many metal halides, e.g. ] and ], giving complexes that are soluble in organic solvents. In such complexes, TMEDA serves as a ]. |
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TMEDA has an affinity for ] ions.<ref name=EROS/> It converts ] into a cluster of higher reactivity than the hexamer. BuLi/TMEDA is able to ] or even doubly metallate many substrates including ], ], ], N-alkyl]s, and ].<ref name=EROS /> Many anionic organometallic complexes have been isolated as their <sup>+</sup> complexes.<ref>{{cite journal | author = Morse, P. M.; Girolami, G. S. | title = Are d<sup>0</sup> ML<sub>6</sub> Complexes Always Octahedral? The X-ray Structure of Trigonal Prismatic <sub>2</sub> | journal = J. Am. Chem. Soc.| year = 1989 | volume = 111 | pages = 4114–5 | doi = 10.1021/ja00193a061}}</ref> In such complexes <sup>+</sup> behaves like a ] salt, such as <sup>+</sup>. |
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TMEDA has an affinity for ] ions.<ref name=EROS/> When mixed with ], TMEDA's nitrogen atoms coordinate to the lithium, forming a cluster of higher reactivity than the tetramer or hexamer that ''n''-butyllithium normally adopts. BuLi/TMEDA is able to ] or even doubly metallate many substrates including ], ], ], ''N''-alkyl]s, and ].<ref name=EROS /> Many anionic organometallic complexes have been isolated as their <sup>+</sup> complexes.<ref>{{cite journal |last1=Morse |first1=P. M. |last2=Girolami |first2=G. S. | title = Are d<sup>0</sup> ML<sub>6</sub> Complexes Always Octahedral? The X-ray Structure of Trigonal Prismatic <sub>2</sub> | journal = ] | year = 1989 | volume = 111 | issue = 11 | pages = 4114–4116 | doi = 10.1021/ja00193a061}}</ref> In such complexes <sup>+</sup> behaves like a ], such as <sup>+</sup>. |
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:] Notice that the diamine is a bidentate ligand.<ref>{{cite journal|first1=K. W. |last1=Henderson |first2=A. E. |last2=Dorigo |first3=Q.-L. |last3=Liu |first4=P. G. |last4=Williard |title=Effect of Polydentate Donor Molecules on Lithium Hexamethyldisilazide Aggregation: An X-ray Crystallographic and a Combination Semiempirical PM3/Single Point ab Initio Theoretical Study |journal=J. Am. Chem. Soc. |date=1997 |volume=119 |issue=49 |page=11855 |doi=10.1021/ja971920t}}</ref>]]{{clear left}} |
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]/TMEDA is a useful combination in organic synthesis where the ''n''-butyl analogue adds to substrate. TMEDA is still capable of forming a metal complex with Li in this case as mentioned above. |
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==Other uses== |
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Tetramethylethylenediamine is used with ] to catalyze the ] of ] when making ]s, used in ], 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. |
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== Safety == |
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==In molecular biology== |
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TEMED is a common reagent in molecular biology laboratories, as a polymerizing agent for ] gels in the protein analysis technique ].<ref name="Manns2011">{{cite journal |doi=10.1002/9780471729259.mca03ms22 |title=SDS-Polyacrylamide Gel Electrophoresis (SDS-PAGE) of Proteins |date=2011 |last1=Manns |first1=Joanne M. |journal=Current Protocols in Microbiology |volume=22 }}</ref> |
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TEMED is highly flammable. Harmful by inhalation and if swallowed. Causes burns. It is better to apply under the hood. |
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==Other uses== |
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The complexes ] and illustrate the use of tmeda to stabilize homogeneous catalysts.<ref name=":1">{{Cite journal |last1=Shields |first1=Jason D. |last2=Gray |first2=Erin E. |last3=Doyle |first3=Abigail G. |date=2015-05-01 |title=A Modular, Air-Stable Nickel Precatalyst |journal=Organic Letters |volume=17 |issue=9 |pages=2166–2169 |doi=10.1021/acs.orglett.5b00766 |pmc=4719147 |pmid=25886092}}</ref> <ref name=":12">{{Cite journal |last1=Magano |first1=Javier |last2=Monfette |first2=Sebastien |date=2015-04-17 |title=Development of an Air-Stable, Broadly Applicable Nickel Source for Nickel-Catalyzed Cross-Coupling |journal=ACS Catalysis |volume=5 |issue=5 |pages=3120–3123 |doi=10.1021/acscatal.5b00498}}</ref> |
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]] |
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==Related compounds== |
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*{{chem2|H2NCMe2\sCMe2NH2}}, also referred to as tetramethylethylenediamine.<ref>{{cite journal |doi=10.1016/j.ica.2003.05.010 |title=Solvent Exchange, Solvent Interchange, Aquation and Isomerisation Reactions of ''cis''- and ''trans''-<sup>3+</sup> in Water, Me<sub>2</sub>SO and MeCN: Kinetics and Stereochemistry |date=2004 |last1=Jackson |first1=W.Gregory |last2=Rahman |first2=A.F.M.Mokhlesur |last3=Wong |first3=M.Anthony |journal=Inorganica Chimica Acta |volume=357 |issue=3 |pages=665–676 }}</ref> |
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*], {{chem2|Me2NCH2NMe2}} |
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==References== |
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==References== |
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