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703540

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

1.0 M in THF

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
NACRES:
NA.22
PubChem Substance ID:
329762048
UNSPSC Code:
12352103
MDL number:
MFCD12546030
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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

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

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

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

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

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP2181
SHBN9202
SHBM6948
SHBL7221
SHBL3467

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Articles

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)
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)
View All Related Papers

Global Trade Item Number

SKUGTIN
703540-100ML04061832821443
703540-4X25ML04061832821481
703540-500ML04061838136459