Cas no 737797-14-7 (2-FLUORO-4-METHYLPHENYLZINC BROMIDE)

2-Fluoro-4-methylphenylzinc bromide is an organozinc reagent commonly used in cross-coupling reactions, such as Negishi and Kumada couplings, due to its high reactivity and selectivity. The presence of both fluorine and methyl substituents on the phenyl ring enhances its utility in constructing complex aromatic frameworks with precise regiocontrol. This compound is typically supplied as a solution in THF or ether, ensuring stability and ease of handling under inert conditions. Its compatibility with a wide range of electrophiles makes it a valuable intermediate in pharmaceutical and agrochemical synthesis. Careful storage under anhydrous and oxygen-free conditions is recommended to maintain its reactivity.
2-FLUORO-4-METHYLPHENYLZINC BROMIDE structure
737797-14-7 structure
Product Name:2-FLUORO-4-METHYLPHENYLZINC BROMIDE
CAS No:737797-14-7
MF:C7H6BrFZn
MW:254.433941364288
MDL:MFCD02260132
CID:978441
PubChem ID:2778854
Update Time:2025-06-29

2-FLUORO-4-METHYLPHENYLZINC BROMIDE Chemical and Physical Properties

Names and Identifiers

    • 2-FLUORO-4-METHYLPHENYLZINC BROMIDE
    • zinc,1-fluoro-3-methylbenzene-6-ide,bromide
    • MFCD02260132
    • 2-Fluoro-4-methylphenylzinc bromide, 0.50 M in THF
    • AKOS016017873
    • 2-Fluoro-4-methylphenylzinc bromide 0.5 M in Tetrahydrofuran
    • 737797-14-7
    • bromozinc(1+);1-fluoro-3-methylbenzene-6-ide
    • bromo(2-fluoro-4-methylphenyl)zinc
    • MDL: MFCD02260132
    • Inchi: 1S/C7H6F.BrH.Zn/c1-6-3-2-4-7(8)5-6;;/h2-3,5H,1H3;1H;/q-1;;+2/p-1
    • InChI Key: ISOHAQUJLZVZQG-UHFFFAOYSA-M
    • SMILES: Br[Zn+].FC1=[C-]C=CC(C)=C1

Computed Properties

  • Exact Mass: 251.89300
  • Monoisotopic Mass: 251.89283g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 182
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 0?2

Experimental Properties

  • PSA: 0.00000
  • LogP: 2.77740

2-FLUORO-4-METHYLPHENYLZINC BROMIDE Security Information

2-FLUORO-4-METHYLPHENYLZINC BROMIDE Pricemore >>

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Additional information on 2-FLUORO-4-METHYLPHENYLZINC BROMIDE

Recent Advances in the Application of 2-Fluoro-4-methylphenylzinc Bromide (CAS: 737797-14-7) in Chemical Biology and Pharmaceutical Research

The organozinc reagent 2-Fluoro-4-methylphenylzinc bromide (CAS: 737797-14-7) has recently emerged as a valuable building block in medicinal chemistry and drug discovery. This compound, belonging to the class of arylzinc halides, demonstrates unique reactivity patterns that make it particularly useful for the synthesis of fluorinated bioactive molecules. Recent studies have highlighted its application in Negishi cross-coupling reactions, where it serves as an efficient nucleophile for the formation of carbon-carbon bonds in complex molecular architectures.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility in the synthesis of novel kinase inhibitors. Researchers utilized 2-Fluoro-4-methylphenylzinc bromide as a key intermediate in constructing a series of potent and selective FGFR inhibitors, achieving significant improvements in both potency (IC50 values in the low nanomolar range) and metabolic stability compared to previous generations of inhibitors. The fluorine atom at the 2-position was found to play a crucial role in modulating the compounds' binding affinity through favorable interactions with the kinase hinge region.

In pharmaceutical process chemistry, recent advancements have focused on optimizing the preparation and handling of 2-Fluoro-4-methylphenylzinc bromide. A 2024 publication in Organic Process Research & Development reported improved synthetic protocols that enhance the reagent's stability and reduce the formation of byproducts. These developments are particularly important for scale-up operations, where consistent reagent quality is critical for reproducible coupling reactions.

The compound has also found applications in PET (positron emission tomography) tracer development. Researchers have successfully incorporated the 2-fluoro-4-methylphenyl moiety, derived from 737797-14-7, into various tracer molecules targeting neurological receptors. The fluorine atom serves dual purposes - as a synthetic handle for further modifications and as a potential site for 18F radiolabeling, making these derivatives valuable tools for neuroimaging studies.

From a safety and handling perspective, recent studies have provided more comprehensive data on the stability and decomposition pathways of 2-Fluoro-4-methylphenylzinc bromide. These investigations have led to improved storage recommendations (typically under inert atmosphere at -20°C) and handling procedures that minimize the risk of violent reactions with protic solvents or oxidizing agents.

Looking forward, the unique properties of 2-Fluoro-4-methylphenylzinc bromide position it as a key reagent in the development of next-generation pharmaceuticals, particularly in areas requiring fluorinated aromatic systems. Its compatibility with various transition metal catalysts and relatively mild reaction conditions make it an attractive option for constructing complex molecules with precise control over stereochemistry and functional group placement.

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