411019

N,N,N′,N′-Tetramethylethylenediamine

≥99.5%, purified by redistillation

• Synonym(s): 1,2-Bis(dimethylamino)ethane, TEMED, TMEDA
• Linear Formula: (CH₃)₂NCH₂CH₂N(CH₃)₂
• CAS Number: 110-18-9
• Molecular Weight: 116.20
• Beilstein: 1732991
• EC Number: 203-744-6
• MDL number: MFCD00008335
• UNSPSC Code: 12352100
• PubChem Substance ID: 24865721
• NACRES: NA.22

Properties

• Quality Level: 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

Description

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.[1] Ultrafast molecular structural dynamics of the charge transfer in N,N,N′,N′-tetramethylethylenediamine has been studied by Rydberg fingerprint spectroscopy.[2]

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).

Safety Information

• Pictograms: GHS02,GHS06,GHS05
• Signal Word: Danger
• Hazard Statements: H225,H302,H314,H331
• Precautionary Statements: P210 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 1
• Flash Point(F): 61.7 °F - closed cup
• Flash Point(C): 16.5 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves