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N,N,N',N'-Tetramethylmethylenediamine is a reagent used as a convenient source of the Mannich intermediate.
Itaru Natori.; Shohei Inoue. Anionic Polymerization of 1,3-Cyclohexadiene with Alkyllithium/Amine Systems. Characteristics of n-Butyllithium/N,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).
Hazard Statements: H225-H314-H318
Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P201-P280a-P304+P340-P405-P501a
Obtain special instructions before use. Wear protective gloves and eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.