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656984

Sigma-Aldrich

Isopropylmagnesium chloride lithium chloride complex solution

1.3 M in THF

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Synonym(s):
Turbo Grignard
Linear Formula:
(CH3)2CHMgCl · LiCl
Molecular Weight:
145.24
MDL number:
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

100
200

concentration

1.3 M in THF

density

0.951 g/mL at 25 °C

SMILES string

[Li]Cl.CC(C)[Mg]Cl

InChI

1S/C3H7.2ClH.Li.Mg/c1-3-2;;;;/h3H,1-2H3;2*1H;;/q;;;2*+1/p-2

InChI key

CWTUREABAILGIK-UHFFFAOYSA-L

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This Item
757969703540360023
density

0.951 g/mL at 25 °C

density

0.952 g/mL at 25 °C

density

0.96 g/mL at 25 °C

density

0.956 g/mL at 25 °C

Quality Level

100, 200

Quality Level

100

Quality Level

100

Quality Level

100

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

Application

Reagent for Selective Metalations

Used for:
  • Preparation of functionalized acyclic alkenyl magnesium reagents/preparation of 1,2-diketones
  • Preparation of cyclic alkenyl and dienyl magnesium reagents
  • Preparation of functionalized triazenes/preparation of carbazoles
  • Regioselective functionalization of trisubstituted pyridines
  • Electrophilic amination for preparation of amines
  • Preparation of Grignards reagents in the presence of masked ketones and aldehydes (using readily deprotectable silylated cyanohydrins)
  • Preparation of Benzylic Grignards via Sulfur-Magnesium exchange
  • Functionalization via I-Mg Exchange of unprotected aromatic and heteroaromatic carboxylic acids
  • Functionalization via I-Mg Exchange of unprotected imidazoles
  • Pyridyne formation
  • Functionalization of cyclopentene derivatives
  • Preparation of 2,3-functionalized furans, benzofurans, and thiophenes
  • Stereoselective synthesis of substituted cyclopropanes
Reagent used with CH3MgCl/LiCl to affect magnesium-halogen exchange on unprotected aryl carboxylic acids.

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 - Skin Corr. 1B

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F

Flash Point(C)

-17 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Felix Kopp et al.
Chemical communications (Cambridge, England), (20), 2075-2077 (2007-08-24)
The magnesiation of halogenated aromatic and heteroaromatic carboxylic acids is accomplished by their treatment with MeMgCl in the presence of LiCl and subsequent reaction with i-PrMgCl.LiCl; the resulting double-magnesiated species react with a variety of electrophiles in up to 97%

Articles

Selective Metalations using i-PrMgCl·LiCl and s-BuMgCl·LiCl

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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