411019
N,N,N′,N′-Tetramethylethylenediamine
≥99.5%, purified by redistillation
Synonym(s):
1,2-Bis(dimethylamino)ethane, TEMED, TMEDA
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About This Item
Linear Formula:
(CH3)2NCH2CH2N(CH3)2
CAS Number:
Molecular Weight:
116.20
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
203-744-6
Beilstein/REAXYS Number:
1732991
MDL number:
Assay:
≥99.5%
Form:
liquid
Quality Level
assay
≥99.5%
form
liquid
purified by
redistillation
expl. lim.
9.08 %
refractive index
n20/D 1.4179 (lit.)
bp
120-122 °C (lit.)
mp
−55 °C (lit.)
density
0.775 g/mL at 20 °C (lit.)
functional group
amine
SMILES string
CN(C)CCN(C)C
InChI
1S/C6H16N2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
InChI key
KWYHDKDOAIKMQN-UHFFFAOYSA-N
General description
N,N,N′,N′-Tetramethylethylenediamine (TMEDA) is a bidentate tertiary amine. It is a Lewis base having good solvating properties. It is useful ligand for organolithium chemistry. Ultrafast molecular structural dynamics of the charge transfer in N,N,N′,N′-tetramethylethylenediamine has been studied by Rydberg fingerprint spectroscopy.
Application
- Hydrogenolysis of Cationic Half-Sandwich Zinc Complexes Containing a Chelating Amine: Facile Cleavage of Zinc-Carbon Bond by Dihydrogen To Give Zinc Hydride Cations.: This research explores the hydrogenolysis of cationic zinc complexes facilitated by N,N,N′,N′-Tetramethylethylenediamine (TMEDA), emphasizing the cleavage of zinc-carbon bonds, contributing significantly to catalyst development and organic synthesis (Mahawar et al., 2024, DOI: 10.1002/chem.202401262).
- Electrophoresis.: This study highlights the use of TMEDA in electrophoresis applications, enhancing the resolution and efficiency of protein and nucleic acid separations, vital for biochemical research (Sonagra & Dholariya, 2024, PubMed ID: 36251838).
- Dihydrogen Cleavage by a Zinc-Zinc Bond of a Heteroleptic Dizinc(I) Cation.: TMEDA is utilized in the activation of zinc-zinc bonds for hydrogen cleavage, demonstrating its importance in inorganic chemistry and catalyst development (Mahawar et al., 2024, DOI: 10.1021/acs.inorgchem.4c01116).
- Nontoxic Initiator Alternatives to TEMED for Redox Hydrogel Polymerization.: The study investigates safer alternatives to TMEDA for hydrogel polymerization, essential for biomedical applications and polymer chemistry (Pumford et al., 2024, DOI: 10.1021/acsabm.3c01264).
- Photoinduced Alkylsulfonylation and Cyanoalkylsulfonylation of Morita-Baylis-Hillman Adducts via Multicomponent Insertion of Sulfur Dioxide.: This paper discusses the role of TMEDA in facilitating multicomponent reactions for organic synthesis, crucial for developing new synthetic methodologies (Song et al., 2024, DOI: 10.1021/acs.joc.4c00052).
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Danger
hcodes
Hazard Classifications
Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B
Storage Class
3 - Flammable liquids
wgk
WGK 1
flash_point_f
61.7 °F - closed cup
flash_point_c
16.5 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Xinxin Cheng et al.
The journal of physical chemistry. A, 119(12), 2813-2818 (2015-02-26)
We have explored the ultrafast molecular structural dynamics associated with charge transfer in N,N,N',N'-tetramethylethylenediamine using Rydberg fingerprint spectroscopy in conjunction with self-interaction corrected density functional theory. Excitation at 239 nm prepares the molecule in the Franck-Condon region of the 3s
Hajime Mori et al.
The Journal of organic chemistry, 71(24), 9004-9012 (2006-11-18)
The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D(2)O quenching. In this paper, the full details of the examples of
Organometallic p-complexes XII. The metalation of benzene and ferrocene by n-butyllithium-N, N, N', N'-tetramethylethylenediamine
Rausch MD and Ciappenelli DJ.
Journal of Organometallic Chemistry, 10(1), 127-136 (1967)