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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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
Marina V Novoselova et al.
Colloids and surfaces. B, Biointerfaces, 181, 680-687 (2019-06-22)
High intensity focused ultrasound (HIFU) is widely used in medical practice, including cancer therapy. Also this approach is promising for remote release of encapsulated drugs in various other biomedical applications where local treatment is needed. Our approach underpins the minimization
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)