Cas no 1359839-23-8 (4-Chloro-3-fluorobenzylzinc bromide)

4-Chloro-3-fluorobenzylzinc bromide is a highly reactive organozinc reagent commonly employed in cross-coupling reactions, such as Negishi or Kumada couplings, due to its excellent selectivity and stability under controlled conditions. The presence of both chloro and fluoro substituents on the benzyl ring enhances its utility in synthesizing complex aromatic compounds, particularly in pharmaceutical and agrochemical applications. This reagent offers precise functionalization capabilities, enabling the introduction of the 4-chloro-3-fluorobenzyl moiety into target molecules with high efficiency. Its compatibility with a wide range of catalysts and substrates makes it a valuable tool for advanced synthetic organic chemistry. Proper handling under inert conditions is recommended to maintain reactivity.
4-Chloro-3-fluorobenzylzinc bromide structure
1359839-23-8 structure
Product Name:4-Chloro-3-fluorobenzylzinc bromide
CAS No:1359839-23-8
MF:C7H5BrClFZn
MW:288.879000425339
CID:6578260
PubChem ID:131847250
Update Time:2026-03-11

4-Chloro-3-fluorobenzylzinc bromide Chemical and Physical Properties

Names and Identifiers

    • 4-Chloro-3-fluorobenzylzinc bromide
    • 4-Chloro-3-fluorobenzylzinc bromide, 0.50 M in THF
    • MFCD22684838
    • bromozinc(1+);1-chloro-2-fluoro-4-methanidylbenzene
    • 1359839-23-8
    • Inchi: 1S/C7H5ClF.BrH.Zn/c1-5-2-3-6(8)7(9)4-5;;/h2-4H,1H2;1H;/q;;+1/p-1
    • InChI Key: PVHCYFRTXRULQX-UHFFFAOYSA-M
    • SMILES: C(C1C=CC(Cl)=C(F)C=1)[Zn]Br

Computed Properties

  • Exact Mass: 285.85386g/mol
  • Monoisotopic Mass: 285.85386g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 104
  • 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

4-Chloro-3-fluorobenzylzinc bromide Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
abcr
AB570436-50 ml
4-Chloro-3-fluorobenzylzinc bromide, 0.50 M in THF; .
1359839-23-8
50 ml
€1155.00 2024-04-19
abcr
AB570436-100 ml
4-Chloro-3-fluorobenzylzinc bromide, 0.50 M in THF; .
1359839-23-8
100 ml
€1808.60 2024-04-19
abcr
AB570436-50ml
4-Chloro-3-fluorobenzylzinc bromide, 0.50 M in THF; .
1359839-23-8
50ml
€1155.00 2024-08-02
abcr
AB570436-100ml
4-Chloro-3-fluorobenzylzinc bromide, 0.50 M in THF; .
1359839-23-8
100ml
€1808.60 2024-08-02

Additional information on 4-Chloro-3-fluorobenzylzinc bromide

4-Chloro-3-fluorobenzylzinc bromide (CAS No. 1359839-23-8)

4-Chloro-3-fluorobenzylzinc bromide (CAS No. 1359839-23-8) is a versatile organometallic compound that has garnered significant attention in the fields of organic synthesis, materials science, and drug discovery. This compound, characterized by its unique structure and reactivity, serves as a valuable building block in the construction of complex molecules. The benzylzinc bromide framework, with its chlorine and fluorine substituents at the 4 and 3 positions respectively, offers a platform for diverse chemical transformations.

Recent advancements in organometallic chemistry have highlighted the potential of 4-chloro-3-fluorobenzylzinc bromide in cross-coupling reactions, particularly in the Suzuki-Miyaura coupling. This reaction enables the formation of biaryl compounds, which are crucial intermediates in pharmaceuticals and agrochemicals. The presence of electron-withdrawing groups (EWGs) such as chlorine and fluorine on the aromatic ring enhances the reactivity of the compound, making it an ideal substrate for these transformations.

In addition to its role in cross-coupling reactions, 4-chloro-3-fluorobenzylzinc bromide has been employed in nucleophilic aromatic substitution (NAS) reactions. The combination of EWGs on the aromatic ring facilitates the activation of specific positions for substitution, allowing for the synthesis of highly functionalized aromatic compounds. This property is particularly advantageous in the development of heterocyclic frameworks, which are prevalent in medicinal chemistry.

The synthesis of 4-chloro-3-fluorobenzylzinc bromide typically involves a two-step process: first, the preparation of the corresponding aryl halide, followed by transmetallation with zinc bromide. This method ensures high purity and stability of the final product. Recent studies have explored alternative synthetic routes, including microwave-assisted synthesis and continuous flow processes, to improve efficiency and scalability.

From a materials science perspective, benzylzinc bromide derivatives like CAS No. 1359839-23-8 are being investigated for their potential in organic electronics. The ability to tune electronic properties through substituent effects opens avenues for applications in flexible electronics and optoelectronic devices.

In conclusion, 4-chloro-3-fluorobenzylzinc bromide (CAS No. 1359839-23-8) stands as a testament to the ingenuity of modern organometallic chemistry. Its unique structure, reactivity, and versatility continue to drive innovation across multiple disciplines. As research progresses, this compound is poised to play an even more pivotal role in advancing both academic and industrial applications.

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