Cas no 144806-52-0 (Benzene, 4-(bromomethyl)-2-chloro-1-nitro-)

Benzene, 4-(bromomethyl)-2-chloro-1-nitro-, is a halogenated nitroaromatic compound with a bromomethyl substituent, offering versatile reactivity in organic synthesis. The presence of both bromomethyl and chloro groups enables selective functionalization, making it a valuable intermediate for cross-coupling reactions, nucleophilic substitutions, and further derivatization. The nitro group enhances electrophilic character, facilitating aromatic substitution reactions. This compound is particularly useful in pharmaceutical and agrochemical research, where precise modification of aromatic frameworks is required. Its stability under standard conditions ensures reliable handling, while its multifunctional structure allows for efficient incorporation into complex molecular architectures. Suitable for controlled reactions, it serves as a key precursor in the synthesis of specialized fine chemicals.
Benzene, 4-(bromomethyl)-2-chloro-1-nitro- structure
144806-52-0 structure
Product Name:Benzene, 4-(bromomethyl)-2-chloro-1-nitro-
CAS No:144806-52-0
MF:C7H5BrClNO2
MW:250.477100133896
CID:1016083
PubChem ID:67193371
Update Time:2025-10-30

Benzene, 4-(bromomethyl)-2-chloro-1-nitro- Chemical and Physical Properties

Names and Identifiers

    • Benzene, 4-(bromomethyl)-2-chloro-1-nitro-
    • 4-(bromomethyl)-2-chloro-1-nitrobenzene
    • WPFRTERBMAUPIM-UHFFFAOYSA-N
    • Benzene,4-(bromomethyl)-2-chloro-1-nitro-
    • G74470
    • 3-Chloro-4-nitrobenzyl bromide
    • 144806-52-0
    • DTXSID10736585
    • SCHEMBL1868568
    • Inchi: 1S/C7H5BrClNO2/c8-4-5-1-2-7(10(11)12)6(9)3-5/h1-3H,4H2
    • InChI Key: WPFRTERBMAUPIM-UHFFFAOYSA-N
    • SMILES: BrCC1C=CC(=C(C=1)Cl)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 248.91922g/mol
  • Monoisotopic Mass: 248.91922g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 173
  • 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: 2.9
  • Topological Polar Surface Area: 45.8?2

Benzene, 4-(bromomethyl)-2-chloro-1-nitro- Pricemore >>

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Benzene, 4-(bromomethyl)-2-chloro-1-nitro- Related Literature

Additional information on Benzene, 4-(bromomethyl)-2-chloro-1-nitro-

Benzene, 4-(bromomethyl)-2-chloro-1-nitro- (CAS No. 144806-52-0): A Comprehensive Overview in Modern Chemical Research

The compound Benzene, 4-(bromomethyl)-2-chloro-1-nitro- (CAS No. 144806-52-0) represents a significant molecule in the realm of organic synthesis and pharmaceutical chemistry. Its unique structural features, characterized by the presence of both bromomethyl and nitro substituents, make it a versatile intermediate in the development of various chemical entities. This introduction delves into the compound's properties, synthetic pathways, and its emerging applications in contemporary research.

Structurally, Benzene, 4-(bromomethyl)-2-chloro-1-nitro- is derived from benzene, with modifications that introduce distinct reactivity patterns. The bromomethyl group at the 4-position enhances its capability to participate in nucleophilic substitution reactions, while the chloro and nitro groups at the 2- and 1-positions, respectively, provide additional functional handles for further derivatization. This combination makes it an invaluable building block for constructing more complex molecules.

In recent years, this compound has garnered attention in the pharmaceutical industry due to its potential as a precursor for active pharmaceutical ingredients (APIs). The nitro group can be reduced to an amine, which is a common transformation in drug synthesis, while the bromomethyl group allows for facile introduction of other functional groups via cross-coupling reactions. Such transformations are pivotal in generating novel compounds with therapeutic potential.

One of the most compelling applications of Benzene, 4-(bromomethyl)-2-chloro-1-nitro- is in the synthesis of bioactive molecules. Researchers have leveraged its reactivity to develop inhibitors targeting various biological pathways. For instance, derivatives of this compound have been explored as potential kinase inhibitors, where the nitro and chloro groups serve as anchors for designing molecules that interact with specific protein targets. These studies highlight its role in medicinal chemistry and drug discovery.

The synthetic methodologies for preparing Benzene, 4-(bromomethyl)-2-chloro-1-nitro- have also seen significant advancements. Traditional approaches often involve multi-step sequences starting from commercially available benzene derivatives. However, modern techniques have streamlined these processes, enabling more efficient and scalable synthesis. For example, palladium-catalyzed cross-coupling reactions have been employed to introduce the bromomethyl group with high selectivity and yield.

Moreover, computational studies have played a crucial role in understanding the reactivity of Benzene, 4-(bromomethyl)-2-chloro-1-nitro-. Molecular modeling has provided insights into how different substituents influence its electronic properties and interactions with other molecules. These findings are not only theoretical but also practical, guiding experimentalists in designing synthetic routes that maximize efficiency and minimize unwanted side reactions.

The environmental impact of synthesizing and handling this compound is another area of growing interest. Given its utility in pharmaceutical applications, ensuring sustainable practices is essential. Researchers are exploring greener synthetic routes that reduce waste and hazardous byproducts. Additionally, efforts are underway to develop methods for recycling or safely disposing of leftover quantities to minimize environmental footprint.

Future directions in the study of Benzene, 4-(bromomethyl)-2-chloro-1-nitro- include expanding its applications into new domains such as materials science and agrochemicals. The versatility of its functional groups makes it a promising candidate for developing advanced materials with unique properties or novel crop protection agents. As research continues to uncover new possibilities, this compound is poised to remain a cornerstone in synthetic chemistry.

In conclusion, Benzene, 4-(bromomethyl)-2-chloro-1-nitro- (CAS No. 144806-52-0) stands as a testament to the ingenuity of modern chemical research. Its unique structure and reactivity make it indispensable in various fields, particularly pharmaceuticals and organic synthesis. As scientists continue to explore its potential, we can expect even more innovative applications to emerge from this remarkable molecule.

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