Synonyms:
Dichloro(2,2,6,6-tetramethylpiperidinato)magnesate(1-)lithium(1:1)
2,2,6,6-Tetramethylpiperidinylmagnesiumchloridelithiumchloridecomplexsolution
2,2,6,6-TetraMethylpiperidinylMagnesiuMchloridelithiuMchloridecoMplexsolution1.0MinTHF/toluene
2,2,6,6-TetramethyChemicalbooklpiperidinylmagnesiumchloridelithiumchloridecomplex
piperidinyL
Magnesate(1-),dichloro(2,2,6,6-tetramethylpiperidinato)-,lithium(1:1)
lithium,magnesium,2,2,6,6-tetramethylpiperidin-1-ide,dichloride
Dichloro(2,2,6,6-tetramethylpiperidinato)magnesate(1-)lithium
Molecular Formula:
C9H18Cl2LiMgN
Molecular Weight:
242.4
Categories:
Synthetic Chemistry > Organometallic Reagents > Organolithium Reagents
Product Description:
2,2,6,6-Tetramethylpiperidinylmagnesium chloride lithium chloride (TMPMgCl╖LiCl) is a highly reactive, sterically hindered Hauser base, commonly referred to as a turbo-Grignard reagent. Its structure features a magnesium center coordinated to a bulky 2,2,6,6-tetramethylpiperidinyl (TMP) group and a chloride ion, with lithium chloride (LiCl) serving as a solubilizing and stabilizing additive. This complex is typically supplied as a solution in tetrahydrofuran (THF) and is known for its enhanced kinetic basicity and improved solubility compared to conventional TMP-based magnesium reagents.
This reagent is primarily utilized in organic synthesis for the direct magnesiation of a wide range of functionalized aromatic and heteroaromatic compounds under mild conditions. The presence of LiCl facilitates the formation of kinetically active magnesium species, enabling selective deprotonation at positions that are otherwise difficult to functionalize. The resulting organomagnesium intermediates can be subsequently trapped with various electrophiles (e.g., aldehydes, ketones, alkyl halides)) to construct carbon-carbon or carbon-heteroatom bonds. It is a valuable tool for the preparation of complex pharmaceuticals, agrochemicals, and advanced organic materials.
Due to its high reactivity, TMPMgClбдLiCl is moisture- and air-sensitive and must be handled under an inert atmosphere (e.g., nitrogen or argon). It is commercially available as a standardized solution and is widely employed in both academic research and industrial process development for the efficient synthesis of densely functionalized molecules.