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656984

Isopropylmagnesium chloride lithium chloride complex solution

1.3 M in THF

Synonym(s):

Turbo Grignard

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About This Item

Linear Formula:
(CH3)2CHMgCl · LiCl
Molecular Weight:
145.24
NACRES:
NA.22
PubChem Substance ID:
24884252
UNSPSC Code:
12352103
MDL number:
MFCD07784514
Concentration:
1.3 M in THF
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reaction suitability

reaction type: Grignard Reaction

Quality Level

100

packaging

Sure/Seal™ of

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

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

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Danger

Hazard Classifications

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

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

flash_point_f

1.4 °F

flash_point_c

-17 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT5259
SDBB8475
SHBT1186
SDBB4899
SDBB3861

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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 Metalations

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

View All Articles
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%