N,N,N',N'-Tetramethylmethylenediamine is a reagent used as a convenient source of the Mannich intermediate.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
N,N,N′,N′-Tetramethylmethylenediamine is a reagent used as a convenient source of the Mannich intermediate.
Solubility
Fully miscible in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents.
RUO – Research Use Only
General References:
- Itaru Natori.; Shohei Inoue. Anionic Polymerization of 1,3-Cyclohexadiene with Alkyllithium/Amine Systems. Characteristics of n-Butyllithium,N,N‘,N‘-Tetramethylethylenediamine System for Living Anionic Polymerization. Macromolecules. 1998, 31 (15), 4687-4694.
- Wei-Guang Liu.; Siddharth Dasgupta.; Sergey V. Zybin.; William A. GoddardIII. First Principles Study of the Ignition Mechanism for Hypergolic Bipropellants: N,N,N',N'-Tetramethylethylenediamine (TMEDA) and N,N,N',N'-Tetramethylmethylenediamine (TMMDA) with Nitric Acid. J. Phys. Chem. A. 2011, 115 (20), 5221-5229.
- Has been used as a convenient source of the Mannich intermediate: J. Org. Chem., 33, 1719 (1968). For an example (dimethylaminomethyleneation of ferrocene), see: Org. Synth. Coll., 5, 434 (1973). Reaction with o-hydroxy ɑ-aryl acetophenones leads directly to isoflavanones: Synth. Commun., 29, 3895 (1999):
- Caution! The product of double lithiation has been reported to explode on drying: Org. Process Res. Dev., 7, 1029 (2003).