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Isopropylmagnesium chloride lithium chloride complex solution
656984 -
1.3 M in THF
DOWNLOAD MSDS (PDF)Synonym: Turbo Grignard
Linear Formula: (CH3)2CHMgCl · LiCl
Molecular Weight: 145.24
MDL number: MFCD07784514
PubChem Substance ID: 24884252
Properties
| Related Categories | Alkyl, Chemical Synthesis, Grignard Reagents, Organic Bases, Organometallic Reagents, |
| concentration | 1.3 M in THF |
| density | 0.951 g/mL at 25 °C |
Description
Application
Reagent used with CH3MgCl/LiCl to affect magnesium-halogen exchange on unprotected aryl carboxylic acids.14
Reagent for Selective Metalations
Used for:
• Preparation of functionalized acyclic alkenyl magnesium reagents/preparation of 1,2-diketones1
• Preparation of cyclic alkenyl and dienyl magnesium reagents2
• Preparation of functionalized triazenes/preparation of carbazoles3
• Regioselective functionalization of trisubstituted pyridines4
• Electrophilic amination for preparation of amines5
• Preparation of Grignards reagents in the presence of masked ketones and aldehydes (using readily deprotectable silylated cyanohydrins)6
• Preparation of Benzylic Grignards via Sulfur-Magnesium exchange7
• Functionalization via I-Mg Exchange of unprotected aromatic and heteroaromatic carboxylic acids8
• Functionalization via I-Mg Exchange of unprotected imidazoles9
• Pyridyne formation10
• Functionalization of cyclopentene derivatives11
• Preparation of 2,3-functionalized furans, benzofurans, and thiophenes12
• Stereoselective synthesis of substituted cyclopropanes13
Packaging
100, 800 mL in Sure/Seal™
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Certificate of Analysis
Certificate of Origin
| ChemFiles Vol 7 No 4 (869 KB ) |
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Safety Information
| Symbol |    GHS02, GHS05, GHS07 |
| Signal word | Danger |
| Hazard statements | H225-H314-H335 |
| Precautionary statements | P210-P261-P280-P305 + P351 + P338-P310 |
| Supplemental Hazard Statements | May form explosive peroxides., Reacts violently with water. |
| Personal Protective Equipment | Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
| Hazard Codes | F,C |
| Risk Statements | 14/15-19-34 |
| Safety Statements | 16-26-29-33-36/37/39-43-45 |
| RIDADR | UN 3399 4.3/PG 2 |
| WGK Germany | 3 |
| Flash Point(F) | 1.4 °F |
| Flash Point(C) | -17 °C |
Technical information & documentation associated with this product is available in the Safety & Documentation tab.
Articles
New Reagents for Selective Metalation, Deprotonation, and 1,2-Additions
While halogen-metal exchange reactions are among the most common methods for preparing organometallic reagents, Li-halogen exchange reactions typically require low temperatures and offer limited comp...
Dr. Josephine Nakhla
Chemfiles Volume 10 Article 1
Keywords: Addition reactions, Catalog, Catalysis, Deprotonations, Eliminations, Grignard Reaction, Metallations, Nucleophilic additions, Protocol, Reductions, transformation
Selective Metalations using i-PrMgCl·LiCl and s-BuMgCl·LiCl
While halogen-metal exchange reactions are among the most common methods for preparing reactive organometallic reagents, Li-halogen exchange reactions typically require low temperatures and offer lim...
Aaron Thornton
Chemfiles Volume 11 Article 1
Keywords: Eliminations, Grignard Reaction
Related Content
New Reagents for Selective Metalation, Deprotonation, and Additions
Over the last several years, Knochel and coworkers have reported reagents for selective metalation, deprotonation and nucleophilic additions. These reagents have transformed the field, allowing for u...
References
1. Ren, H.; et al. Org. Lett. 6, 4215, (2004)
2. Ren, H.; et al. Chem. Commun. (Camb.), 543, (2005)
3. Liu, C-Y.; et al. Org. Lett. 7, 2543, (2005)
4. Ren, H.; et al. Chem. Commun. (Camb.), 726, (2006)
5. Sinha, P.; Knochel, P. Synlett 8, 617, (2006)
6. Liu, C.-Y.; et al. Org. Lett. 8, 617, (2006)
7. Stoll. A, H.; et al. Angew. Chem. Int. Ed. Engl. 45, 606, (2006)
8. Kopp, F.; Knochel, P. Synlett, 980, (2007)
9. Kopp, F.; et al. Chem. Commun. (Camb.), 2075, (2007)
10. Lin, W.; et al. Tetrahedron 63, 2787, (2007)
11. Despotopoulou, C.; et al. Chem. Eur. J. 14, 2499, (2008)
12. Melzig, L.; et al. Chem. Commun. (Camb.), 3536, (2009)
13. Rauhut, C. B.; et al. Synlett, 67, (2009)
14. Chem. Commun. (Camb.), 2075, (2007) Abstract
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