2,2,6,6-Tetramethylpiperidide magnesium chloride / lithium chloride, typ. 22% in THF
C9H18ClMgN
2,2,6,6-Tetramethylpiperidinylmagnesium chloride / lithium chloride (TMPMgCl·LiCl, CAS 215863-85-7) is a mixed Mg/Li amide with molecular formula C9H18ClMgN. It is supplied as a typically 22% solution in THF.
It is commonly used as a strong non-nucleophilic base for selective deprotonations. Main applications include deprotonations of (hetero-)arenes often in ortho-position to directing groups.
TMPMgCl·LiCl reacts readily with moisture and oxygen and should be handled under dry, inert conditions. Consult the SDS and site-specific procedures for compatible materials, fire response, and storage.
Applications
Selective deprotonation of arenes and heteroarenes. Arenes and heteroarenes are typically deprotonated by a directed lithiation using organolithium compounds or organolithiumamides (e.g. LDA). The high reactivity and nucleophilicity of these reagents often result in unwanted side reactions and preludes the presence of sensitive functional groups like esters or ketones. Additionally, such deprotonation reactions often require low temperatures leading to higher production costs on larger scale. Due to their low kinetic basicity magnesiumamides tolerate a lot of functional groups.
Specifications
- Magnesium tert-Butoxide: min. 93 %
Method of Analysis
Determination of active base by thermometric titration. Lithiumchloride content is calculated by Lithium content which is measured by FES. Detailed description is available on request.Handling Instructions
Organomagnesium compounds should only be handled under inert gas. Avoid contact with eyes, skin and clothes as well as inhalation. Vapors may form explosive mixtures with air. Vapors are heavier than air and may spread along floors. Flash-back possible over considerable distance. Use only explosion-proof equipment. Take measures against electrostatic discharges. Protect from frost, heat and sunlight. Never add water, acids or oxidizing materials to the product. In case of fire use dry extinguishers on basis of sodium chloride or limestone powder. Never use water or CO2-extinguishers. Pay attention to the SDS.
Storage Instructions
Store in well ventilated areas in tightly closed containers. As material decomposes slowly above room temperature recommended storage temperature is -10°C -+20°C. When stored according to SDS the material has limited stability due to decomposition over time. We therefore recommend to retest the material 6 month after date of analysis if included on CoA. If not included, use the date of manufacturing for the calculation.
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