Cas no 875819-44-6 (2-(3-Bromo-5-nitrophenyl)acetonitrile)

2-(3-Bromo-5-nitrophenyl)acetonitrile is a brominated and nitrated phenylacetonitrile derivative, primarily used as an intermediate in organic synthesis. Its key structural features—a bromo substituent at the 3-position and a nitro group at the 5-position—make it a versatile building block for pharmaceuticals, agrochemicals, and specialty chemicals. The electron-withdrawing nitro and bromo groups enhance reactivity in nucleophilic substitution and coupling reactions, facilitating the construction of complex aromatic frameworks. This compound is particularly valuable in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig amination, due to its halogenated aromatic core. High purity and stability under standard storage conditions ensure consistent performance in synthetic applications.
2-(3-Bromo-5-nitrophenyl)acetonitrile structure
875819-44-6 structure
Product Name:2-(3-Bromo-5-nitrophenyl)acetonitrile
CAS No:875819-44-6
MF:C8H5BrN2O2
MW:241.041500806808
CID:2620843
PubChem ID:53414241
Update Time:2025-10-28

2-(3-Bromo-5-nitrophenyl)acetonitrile Chemical and Physical Properties

Names and Identifiers

    • SCHEMBL4217345
    • 875819-44-6
    • CS-0120975
    • MFCD18392325
    • 3-Bromo-5-nitrophenylacetonitrile
    • DTXSID00696801
    • 2-(3-BROMO-5-NITROPHENYL)ACETONITRILE
    • (3-Bromo-5-nitrophenyl)acetonitrile
    • IEIQKZJDWXZNEO-UHFFFAOYSA-N
    • 2-(3-Bromo-5-nitrophenyl)acetonitrile
    • Inchi: 1S/C8H5BrN2O2/c9-7-3-6(1-2-10)4-8(5-7)11(12)13/h3-5H,1H2
    • InChI Key: IEIQKZJDWXZNEO-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C=C(CC#N)C=1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 239.95344Da
  • Monoisotopic Mass: 239.95344Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 242
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.1
  • Topological Polar Surface Area: 69.6?2

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Additional information on 2-(3-Bromo-5-nitrophenyl)acetonitrile

2-(3-Bromo-5-nitrophenyl)acetonitrile: A Comprehensive Overview

The compound with CAS No 875819-44-6, commonly referred to as 2-(3-Bromo-5-nitrophenyl)acetonitrile, is a highly specialized organic molecule that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound is characterized by its unique structure, which includes a bromine atom at the 3-position and a nitro group at the 5-position of the phenyl ring, with an acetonitrile group attached at the 2-position. The combination of these functional groups imparts distinctive chemical properties, making it a valuable compound for various applications.

Recent studies have highlighted the potential of 2-(3-Bromo-5-nitrophenyl)acetonitrile in drug discovery, particularly in the development of anticancer agents. Researchers have found that the bromine and nitro groups on the phenyl ring contribute to the compound's ability to interact with specific biological targets, such as protein kinases and enzymes involved in cancer cell proliferation. These findings suggest that this compound could serve as a lead molecule for designing more effective and selective anticancer drugs.

In addition to its pharmacological applications, 2-(3-Bromo-5-nitrophenyl)acetonitrile has also been explored in materials science. Its electron-withdrawing groups make it a promising candidate for use in organic electronics, particularly in the development of semiconducting materials. Recent research has demonstrated that this compound can be incorporated into thin-film transistors, exhibiting excellent charge transport properties. This advancement opens up new possibilities for its use in flexible electronics and optoelectronic devices.

The synthesis of 2-(3-Bromo-5-nitrophenyl)acetonitrile involves a multi-step process that typically begins with the bromination of a phenol derivative followed by nitration and subsequent acylation. The reaction conditions are carefully optimized to ensure high yields and purity. Recent advancements in catalytic methods have further improved the efficiency of this synthesis, making it more accessible for large-scale production.

From an environmental perspective, 2-(3-Bromo-5-nitrophenyl)acetonitrile has been studied for its potential as a catalyst in green chemistry processes. Its ability to facilitate selective oxidation reactions under mild conditions has been reported in several recent studies. This property makes it a valuable tool for reducing energy consumption and minimizing waste in industrial chemical processes.

In conclusion, 2-(3-Bromo-5-nitrophenyl)acetonitrile (CAS No 875819-44-6) is a versatile compound with a wide range of applications across multiple disciplines. Its unique chemical structure and functional groups make it an attractive candidate for drug discovery, materials science, and green chemistry. As research continues to uncover new insights into its properties and potential uses, this compound is poised to play an increasingly important role in advancing modern science and technology.

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