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703540

Sigma-Aldrich

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

1.0 M in THF/toluene

Synonym(s):

TMPMgCl·LiCl

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About This Item

Empirical Formula (Hill Notation):
C9H18Cl2LiMgN
CAS Number:
898838-07-8
Molecular Weight:
242.40
MDL number:
MFCD12546030
UNSPSC Code:
12352103
PubChem Substance ID:
329762048
NACRES:
NA.22

form

liquid

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

Application

Selective Deprotonations using Knochel-Hauser-Base
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

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

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

5.0 °F

Flash Point(C)

-15 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Direct, regioselective N-alkylation of 1, 3-azoles.
Chen S
Organic Letters, 18(1), 16-19 (2015)
Highly Functionalized Benzene Syntheses by Directed Mono or Multiple Magnesiations with TMPMgCl.LiCl.
Lin W
Organic Letters, 8(24), 5673-5676 (2006)
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)
Conjugated Polymers with Repeated Sequences of Group 16 Heterocycles Synthesized through Catalyst-Transfer Polycondensation.
Tsai CH
Journal of the American Chemical Society, 138(21), 6798-6804 (2016)
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Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

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