703540

Sigma-Aldrich

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

1.0 M in THF/toluene

Synonym(s):
TMPMgCl·LiCl
Empirical Formula (Hill Notation):
C9H18Cl2LiMgN
CAS Number:
Molecular Weight:
242.40
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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)N1MgCl

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

Related Categories

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.

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

Signal Word

Danger

Target Organs

Respiratory system

Supp Hazards

EUH014 - EUH018 - EUH019

Hazard Codes

F,C

Risk Statement

63-11-14-19-34-37-40

Safety Statement

16-26-36/37/39-45

RIDADR

UN 3399A 4.3(3) / PGI

WGK Germany

WGK 3

Flash Point(F)

5.0 °F

Flash Point(C)

-15 °C

Certificate of Analysis
Certificate of Origin
Scaleable preparation of functionalized organometallics via directed ortho metalation using Mg-and Zn-amide bases.
Wunderlich SH
Organic Process Research & Development, 14(2), 339-345 (2010)
Synthesis of polyfuran and thiophene-furan alternating copolymers using catalyst-transfer polycondensation.
Qiu Y
ACS Macro Letters, 5(3), 332-336 (2016)
Synthesis of fully substituted pyrazoles via regio-and chemoselective metalations.
Despotopoulou C
Organic Letters, 11(15), 3326-3329 (2009)
Hiroki Iguchi et al.
Scientific reports, 7, 39937-39937 (2017-01-07)
Processing and manipulation of highly conductive pristine graphene in large quantities are still major challenges in the practical application of graphene for electric device. In the present study, we report the liquid-phase exfoliation of graphite in toluene using well-defined poly(3-hexylthiophene)...
Highly Functionalized Benzene Syntheses by Directed Mono or Multiple Magnesiations with TMPMgCl.LiCl.
Lin W
Organic Letters, 8(24), 5673-5676 (2006)
Articles
Transformative reagents for selective metalation, deprotonation and nucleophilic additions have allowed for unprecedented selective converstions to reactive intermediates within a molecule which contains sensative functionalities under mild reactions.
Read More
We present an article concerning Reagents for Selective Metalation, Deprotonation, and 1,2-Additions.
Read More

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