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Merck
CN

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:
Molecular Weight:
242.40
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
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Product Name

2,2,6,6-Tetramethylpiperidinylmagnesium chloride lithium chloride complex solution, 1.0 M in THF

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

SMILES string

[Li+].[Cl-].CC1(C)CCCC(C)(C)N1[Mg]Cl

InChI key

JHBZAAACZVPPRQ-UHFFFAOYSA-L

form

liquid

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF
20 % (w/w)

density

0.96 g/mL at 25 °C

storage temp.

2-8°C

Quality Level

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.

Legal Information

Product of Albemarle US Inc
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Packaging

The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

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Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

Storage Class

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

Regulatory Information

危险化学品
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Synthesis of fully substituted pyrazoles via regio-and chemoselective metalations.
Despotopoulou C
Organic Letters, 11(15), 3326-3329 (2009)
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)
Synthesis of polyfuran and thiophene-furan alternating copolymers using catalyst-transfer polycondensation.
Qiu Y
ACS Macro Letters, 5(3), 332-336 (2016)
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)
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 enable selective conversions within molecules containing sensitive functionalities under mild reactions.

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