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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
STBK9025
STBK6344
STBK5064
SHBN9884
SHBN6478

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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

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

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 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.

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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