Cas no 1255574-54-9 (4-Bromo-5-isopropoxy-2-nitroaniline)

4-Bromo-5-isopropoxy-2-nitroaniline is a halogenated nitroaniline derivative with a substituted isopropoxy group, offering unique reactivity in synthetic chemistry applications. Its bromo and nitro functional groups provide versatile sites for nucleophilic substitution and reduction reactions, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes. The isopropoxy moiety enhances solubility in organic solvents, facilitating further derivatization. This compound is particularly useful in cross-coupling reactions and as a precursor for heterocyclic frameworks. High purity and consistent quality ensure reliable performance in research and industrial processes. Proper handling is advised due to its potential sensitivity to light and heat.
4-Bromo-5-isopropoxy-2-nitroaniline structure
1255574-54-9 structure
Product Name:4-Bromo-5-isopropoxy-2-nitroaniline
CAS No:1255574-54-9
MF:C9H11BrN2O3
MW:275.099241495132
MDL:MFCD17214235
CID:1086105
PubChem ID:53216235
Update Time:2025-06-11

4-Bromo-5-isopropoxy-2-nitroaniline Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-5-isopropoxy-2-nitroaniline
    • 4-bromo-2-nitro-5-propan-2-yloxyaniline
    • 1255574-54-9
    • 4-Bromo-2-nitro-5-[(propan-2-yl)oxy]aniline
    • Benzenamine, 4-bromo-5-(1-methylethoxy)-2-nitro-
    • MFCD17214235
    • AKOS015835325
    • DB-367550
    • DTXSID20681491
    • BS-19671
    • MDL: MFCD17214235
    • Inchi: 1S/C9H11BrN2O3/c1-5(2)15-9-4-7(11)8(12(13)14)3-6(9)10/h3-5H,11H2,1-2H3
    • InChI Key: OJJABBOIPJKWDT-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=C(C=C1OC(C)C)N)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 273.99500
  • Monoisotopic Mass: 273.99530g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 232
  • 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: 3.1
  • Topological Polar Surface Area: 81.1?2

Experimental Properties

  • PSA: 81.07000
  • LogP: 3.83110

4-Bromo-5-isopropoxy-2-nitroaniline Customs Data

  • HS CODE:2922299090
  • Customs Data:

    China Customs Code:

    2922299090

    Overview:

    2922299090. Other amino groups(naphthol\phenol)And ether\Esters [including their salts, Except those containing more than one oxygen-containing group]. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, The color of ethanolamine and its salt should be reported, The package of ethanolamine and its salt shall be declared

    Summary:

    2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Additional information on 4-Bromo-5-isopropoxy-2-nitroaniline

Introduction to 4-Bromo-5-isopropoxy-2-nitroaniline (CAS No. 1255574-54-9)

4-Bromo-5-isopropoxy-2-nitroaniline, identified by its Chemical Abstracts Service (CAS) number 1255574-54-9, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science. This compound belongs to the class of nitroaromatic derivatives, characterized by the presence of both bromine and isopropoxy substituents on a benzene ring, further functionalized by a nitro group. The unique structural arrangement of these substituents imparts distinct chemical properties, making it a valuable intermediate in the synthesis of various biologically active molecules.

The nitroaniline core structure of this compound is well-documented for its role in medicinal chemistry, particularly in the development of antimicrobial, antitumor, and anti-inflammatory agents. The bromo and isopropoxy groups introduce further reactivity, enabling diverse chemical transformations such as cross-coupling reactions, nucleophilic substitutions, and selective hydrogenations. These modifications are crucial for tailoring the pharmacokinetic and pharmacodynamic profiles of drug candidates.

In recent years, there has been a surge in research focused on developing novel therapeutic agents with enhanced efficacy and reduced side effects. 4-Bromo-5-isopropoxy-2-nitroaniline has emerged as a key building block in this endeavor. Its structural features make it an excellent candidate for generating scaffolds that interact with biological targets with high specificity. For instance, studies have demonstrated its utility in designing small-molecule inhibitors targeting enzymes involved in cancer metabolism. The nitro group can be reduced to an amine, facilitating further derivatization into more complex structures with potential therapeutic applications.

The isopropoxy moiety, in particular, has been recognized for its ability to modulate solubility and metabolic stability in drug molecules. This property is critical for improving oral bioavailability and prolonging the half-life of administered drugs. Researchers have leveraged this characteristic to develop prodrugs that release active pharmaceutical ingredients (APIs) under specific physiological conditions. Such innovations align with the broader goal of precision medicine, where drug delivery systems are tailored to individual patient needs.

Advances in synthetic methodologies have further expanded the utility of 4-Bromo-5-isopropoxy-2-nitroaniline. Transition-metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, have enabled the introduction of aryl or heteroaryl groups at various positions on the benzene ring. These reactions are pivotal for constructing polycyclic aromatic systems that mimic natural products or known bioactive compounds. The ability to precisely control regioselectivity has opened new avenues for drug discovery.

From a materials science perspective, derivatives of 4-Bromo-5-isopropoxy-2-nitroaniline have been explored for their potential applications in organic electronics. Nitroaromatic compounds are known for their electron-withdrawing properties, which can enhance charge transport in semiconducting materials. Researchers have investigated these derivatives as components in organic light-emitting diodes (OLEDs) and photovoltaic cells. The presence of bromine and isopropoxy groups allows for further functionalization via polymerization or copolymerization techniques, leading to materials with tailored optoelectronic properties.

The synthesis of 4-Bromo-5-isopropoxy-2-nitroaniline itself presents an interesting challenge due to the need for precise regiocontrol during functionalization. Current methodologies often involve multi-step processes starting from commercially available anilines or nitrobenzenes. Recent developments have focused on greener synthetic routes, employing catalytic systems that minimize waste and energy consumption. For example, microwave-assisted synthesis has been shown to accelerate reaction times while maintaining high yields.

In clinical research, 4-Bromo-5-isopropoxy-2-nitroaniline has been used as a precursor in the development of novel antibiotics targeting resistant bacterial strains. The nitro group can be converted into an amide or ester linkage, which is a common motif in antibiotic scaffolds. Additionally, computational modeling has been employed to predict binding affinities between this compound and bacterial enzymes involved in DNA replication or metabolic pathways. Such simulations accelerate the identification of lead compounds that require further optimization.

The future prospects of 4-Bromo-5-isopropoxy-2-nitroaniline are promising, given its versatility as a synthetic intermediate and its potential applications across multiple disciplines. As computational chemistry tools become more sophisticated, virtual screening methods will likely play a larger role in identifying new derivatives with enhanced biological activity. Furthermore, collaborations between academia and industry are expected to drive innovation by combining experimental expertise with industrial-scale production capabilities.

In conclusion,4-Bromo-5-isopropoxy-2-nitroaniline (CAS No. 1255574-54-9) represents a cornerstone compound in modern chemical research. Its unique structural features enable diverse applications ranging from pharmaceutical development to advanced materials design。 The ongoing exploration of its synthetic possibilities and biological relevance underscores its importance as a research tool。 As scientific understanding evolves,this compound will undoubtedly continue to inspire new discoveries that benefit society。

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