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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

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Isopropylmagnesium chloride lithium chloride complex solution 1.3 M in THF

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Sigma-Aldrich

360023

o-Tolylmagnesium chloride solution

concentration

1.3 M in THF

concentration

1.0 M in THF

concentration

1.0 M in THF, 20 % (w/w)

concentration

1.0 M in THF

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

packaging

Sure/Seal™ of

packaging

Sure/Seal™ of

packaging

Sure/Seal™ of

packaging

Sure/Seal™ of

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.[1]

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
SHBT1186
SDBB4899
SDBB3861
SDBB2947

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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 Metalation and Additions

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

Selective Metalations

Salt additives increase both the rate and the efficiency of the Mg-halogen exchange reaction. The most effective reagents are generated with R-MgCl (R = i-Pr, s-Butyl) and 1.0 equiv of LiCl.

Global Trade Item Number

SKUGTIN
656984-100ML04061832733425
656984-4X25ML04061832733432
656984-800ML04061832733449
656984-2L04061838120519
656984-800ML-PM04065271006645

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