ALLYLMAGNESIUM BROMIDE

Base Information

• Chemical Name: ALLYLMAGNESIUM BROMIDE
• CAS No.: 1730-25-2
• Molecular Formula: C3H5BrMg
• Molecular Weight: 145.282
• Hs Code.: 29319090
• Mol file: 1730-25-2.mol

Synonyms:Allylmagnesiumbromide (6CI);Magnesium, allylbromo- (7CI,8CI);2-Propenylmagnesium bromide;Allylbromomagnesium;Bromo(2-propenyl)magnesium;

Chemical Property of ALLYLMAGNESIUM BROMIDE

Chemical Property:

• Flash Point: -40 °C
• PSA: 0.00000
• Density: 0.851 g/cm³
• LogP: 1.98560
• Storage Temp.: Refrigerator
• Sensitive.: air sensitive, moisture sensitiv

Purity/Quality:

99% ^*data from raw suppliers

Allyl magnesium bromide solution ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F+; C
• Hazard Codes: F+,C,F
• Statements: 12-14/15-19-22-34-66-67-11
• Safety Statements: 9-16-29-33-43-45-36/37/39-26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• General Description: Allylmagnesium bromide is a Grignard reagent that has been utilized in copper-catalyzed asymmetric conjugate addition reactions, demonstrating effectiveness in generating enantioenriched products with good diastereoselectivity. In the context of the study, it was found to exhibit the best enantioselectivity when reacting with specific substrates, such as 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes, particularly when paired with certain Josiphos ligands. This reagent plays a key role in forming 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-2-branched alkanes, highlighting its utility in stereoselective transformations.

Technology Process of ALLYLMAGNESIUM BROMIDE

There total 18 articles about ALLYLMAGNESIUM BROMIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

diallylamine (124-02-7) → allylmagnesium bromide (1730-25-2)

Guidance literature:

With triethylamine;

Reference yield: 82.0%

→ allylmagnesium bromide (1730-25-2)

Guidance literature:

Reference yield: 73.0%

→ tricyclo[4.2.1.02,5 ]non-7-en-3-ylmethanol (53201-70-0) + allylmagnesium bromide (1730-25-2)

Guidance literature:

upstream raw materials:

9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium

allyl bromide

1,3-dibromo-propane

1,3-bis(bromomagnesio)propane

Downstream raw materials:

n-Pent-4-enyl alcohol

2-n-Propylquinoline

2-allyl-1,2-dihydro-quinoline

1-(2-pyridinyl)but-3-en-1-ol

Refernces

Copper-catalyzed asymmetric conjugate addition of Grignard reagents to 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes

10.1016/j.tetasy.2009.06.001

The research investigates the copper-catalyzed asymmetric conjugate addition of Grignard reagents to 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes, aiming to produce 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-2-branched alkanes with enantioenrichment. The study screens various copper ligands, finding that certain Josiphos ligands provide low to moderate enantioselectivity and good diastereoselectivity when using allylmagnesium bromide. The stereochemistry of the products is assigned by comparing them with those synthesized via chiral pool synthesis and stereoselective lithiation methods. The research concludes that most typical copper ligands slow down the addition reaction, and substrate 5b with allylmagnesium bromide shows the best enantioselectivity. Key chemicals used include 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes as substrates, Grignard reagents like isopropenylmagnesium bromide and allylmagnesium bromide, and various copper ligands such as Josiphos and NHC ligands.