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-H335
Highly flammable liquid and vapour. Causes severe skin burns and eye damage. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant