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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:
110-18-9
Molecular Weight:
116.20
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24865721
EC Number:
203-744-6
Beilstein/REAXYS Number:
1732991
MDL number:
MFCD00008335
Assay:
≥99.5%
Form:
liquid
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Quality Segment

200

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

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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