Skip to Content
Merck

Key Documents

View All Documentation

703540

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

1.0 M in THF

Synonym(s):

TMPMgCl·LiCl

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C9H18Cl2LiMgN
CAS Number:
898838-07-8
Molecular Weight:
242.40
NACRES:
NA.22
PubChem Substance ID:
329762048
UNSPSC Code:
12352103
MDL number:
MFCD12546030
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

form

liquid

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

packaging

Sure/Seal™ of

concentration

1.0 M in THF, 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

signalword

Danger

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

flash_point_f

5.0 °F

flash_point_c

-15 °C

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Central nervous system, Respiratory system

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBP2181
SHBN9202
SHBM6948
SHBL7221
SHBL3467

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

Selective Metalation, Deprotonation, and Additions

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.

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

Sigma-Aldrich.com presents an article concerning New Reagents for Selective Metalation, Deprotonation, and 1,2-Additions.

Selective Metalation and Additions

Transformative reagents enable selective conversions within molecules containing sensitive functionalities under mild reactions.

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)
Direct, regioselective N-alkylation of 1, 3-azoles.
Chen S
Organic Letters, 18(1), 16-19 (2015)
View All Related Papers