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656984

Sigma-Aldrich

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
MDL number:
MFCD07784514
UNSPSC Code:
12352103
PubChem Substance ID:
24884252
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

Related Categories

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 Statements

H225,H314,H335,H336,H351

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH014,EUH019

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

656984-4X10ML:
656984-BULK:
656984-20ML:
656984-100ML:4548173224800
656984-4X25ML:4548173305981
656984-2L:4548173912554
656984-VAR:
656984-800ML-PM:
656984-10ML:4548173224817
656984-800ML:4548173300207
656984-PZ:

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4051
STBL4582
STBL4791
STBL3355
STBL2633

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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

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.

Selective Metalation and Additions

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

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