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703540 Sigma-Aldrich

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

1.0 M in THF/toluene

Synonym: TMPMgCl·LiCl

  • CAS Number 898838-07-8

  • Empirical Formula (Hill Notation) C9H18Cl2LiMgN

  • Molecular Weight 242.40

  •  MDL number MFCD12546030

  •  PubChem Substance ID 329762048

  •  NACRES NA.22

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Properties

Related Categories 25mL Sure/Seal Reagents, Chemical Synthesis, Grignard Reagents, Heteroaryl, Organometallic Reagents More...
reaction suitability   reaction type: Grignard Reaction
concentration   1.0 M in THF/toluene
  20 % (w/w)
density   0.96 g/mL at 25 °C
storage temp.   2-8°C
SMILES string   [Li+].[Cl-].CC1(C)CCCC(C)(C)N1[Mg]Cl
InChI   1S/C9H18N.2ClH.Li.Mg/c1-8(2)6-5-7-9(3,4)10-8;;;;/h5-7H2,1-4H3;2*1H;;/q-1;;;+1;+2/p-2
InChI key   JHBZAAACZVPPRQ-UHFFFAOYSA-L

Description

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

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

Safety & Documentation

Safety Information

Signal word 
Danger
Target organs 
Respiratory system
Supplemental Hazard Statements 
EUH014 - EUH018 - EUH019
RIDADR 
UN 3399A 4.3(3) / PGI
WGK Germany 
WGK 3
Flash Point(F) 
5.0 °F
Flash Point(C) 
-15 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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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

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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