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703540 Aldrich

2,2,6,6-Tetramethylpiperidinylmagnesium chloride lithium chloride complex solution

1.0 M in THF/toluene

Synonym: TMPMgCl·LiCl

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Properties

Related Categories 25mL Sure/Seal Reagents, Chemical Synthesis, Grignard Reagents, Heteroaryl, Organometallic Reagents More...
InChI Key   JHBZAAACZVPPRQ-UHFFFAOYSA-L
concentration   1.0 M in THF/toluene
  20 % (w/w)
density   0.96 g/mL at 25 °C
storage temp.   2-8°C

Description

Packaging

4×25, 100, 500 mL in Sure/Seal™

The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Product of Albemarle US Inc

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Application

2,2,6,6-Tetramethylpiperidinylmagnesium chloride lithium chloride complex is a non-nucleophilic Knochel-Hauser base mainly used for the magnesiation of functionalized arenes and heteroarenes to prepare the corresponding Grignard reagents. It can also be used as a base in the synthesis of Π-conjugated polymers via catalyst-transfer polycondensation.

Selective Deprotonations using Knochel-Hauser-Base

Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
May form explosive peroxides., Reacts violently with water.
RIDADR 
UN 3399A 4.3(3) / PGI
WGK Germany 
3
Flash Point(F) 
5 °F
Flash Point(C) 
-15 °C

Documents

Certificate of Analysis

Certificate of Origin


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Protocols & Articles

Articles

Discover Reagents for Selective Metalations and Additions from Sigma-Aldrich

From our library of Articles, Sigma-Aldrich presents Discover Reagents for Selective Metalations and Additions from Sigma-Aldrich
William Sommer
Aldrich ChemFiles 2009, 9.6, 11.

New Reagents for Selective Metalation, Deprotonation, and 1,2-Additions

While halogen-metal exchange reactions are among the most common methods for preparing organometallic reagents, Li-halogen exchange reactions typically require low temperatures and offer limited comp...
Dr. Josephine Nakhla
Chemfiles Volume 10 Article 1
Keywords: Addition reactions, Catalysis, Deprotonations, Eliminations, Grignard Reaction, Metallations, Nucleophilic additions, Reductions, transformation

Related Content

New Reagents for Selective Metalation, Deprotonation, and Additions

Over the last several years, Knochel and coworkers have reported reagents for selective metalation, deprotonation and nucleophilic additions. These reagents have transformed the field, allowing for u...
Keywords: Addition reactions, Aminations, Applications, Catalysis, Cross couplings, Deprotonations, Eliminations, Grignard Reaction, Metallations, Methods, Nucleophilic additions, Reductions, Size-exclusion chromatography, transformation

Peer-Reviewed Papers
15

References

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