Cas no 355814-56-1 (4-bromo-N-(4-nitrobenzyl)aniline)

4-Bromo-N-(4-nitrobenzyl)aniline is a brominated aromatic amine derivative featuring both a nitrobenzyl and an aniline moiety. This compound is of interest in synthetic organic chemistry due to its versatile reactivity, particularly in the formation of complex heterocycles and pharmaceutical intermediates. The presence of the electron-withdrawing nitro group and the electron-donating aniline group provides a balanced electronic profile, facilitating selective functionalization. Its bromine substituent enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling further structural diversification. The compound is typically employed in research settings for the development of novel bioactive molecules or advanced materials. Proper handling is required due to potential sensitivity to light and moisture.
4-bromo-N-(4-nitrobenzyl)aniline structure
355814-56-1 structure
Product Name:4-bromo-N-(4-nitrobenzyl)aniline
CAS No:355814-56-1
MF:C13H11BrN2O2
MW:307.142642259598
CID:2602322
PubChem ID:743156
Update Time:2025-11-07

4-bromo-N-(4-nitrobenzyl)aniline Chemical and Physical Properties

Names and Identifiers

    • AB00089188-01
    • N-(4-BROMOPHENYL)-N-(4-NITROBENZYL)AMINE
    • 4-bromo-N-(4-nitrobenzyl)aniline
    • 355814-56-1
    • AKOS000254201
    • STK145915
    • 4-Bromo-N-(4-nitrobenzyl)aniline, AldrichCPR
    • Inchi: 1S/C13H11BrN2O2/c14-11-3-5-12(6-4-11)15-9-10-1-7-13(8-2-10)16(17)18/h1-8,15H,9H2
    • InChI Key: LGBKNMBMJZIWBS-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(=CC=1)NCC1C=CC(=CC=1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 306.00039Da
  • Monoisotopic Mass: 306.00039Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 3
  • Complexity: 267
  • 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: 3.9
  • Topological Polar Surface Area: 57.9?2

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Additional information on 4-bromo-N-(4-nitrobenzyl)aniline

Comprehensive Overview of 4-Bromo-N-(4-Nitrobenzyl)aniline (CAS No. 355814-56-1)

4-Bromo-N-(4-nitrobenzyl)aniline, with the CAS number 355814-56-1, is a versatile organic compound that has garnered significant attention in the fields of chemical synthesis, pharmaceutical research, and materials science. This compound is characterized by its unique molecular structure, which includes a bromo group, an aniline moiety, and a nitrobenzyl substituent. These functional groups endow the compound with a range of chemical properties that make it a valuable intermediate in various synthetic pathways.

The molecular formula of 4-bromo-N-(4-nitrobenzyl)aniline is C13H11BrN2O2, and its molecular weight is approximately 297.14 g/mol. The compound is typically obtained as a solid at room temperature and exhibits good solubility in common organic solvents such as dichloromethane, acetone, and dimethylformamide (DMF). These solubility properties facilitate its use in a variety of chemical reactions and processes.

In recent years, 4-bromo-N-(4-nitrobenzyl)aniline has been extensively studied for its potential applications in pharmaceutical research. One notable area of interest is its use as an intermediate in the synthesis of novel drugs targeting various diseases. For instance, researchers have explored the compound's role in the development of anti-inflammatory agents and anticancer drugs. The bromo and nitro groups provide opportunities for further functionalization, allowing chemists to tailor the compound's properties to meet specific therapeutic needs.

A recent study published in the Journal of Medicinal Chemistry highlighted the use of 4-bromo-N-(4-nitrobenzyl)aniline as a key intermediate in the synthesis of a new class of selective serotonin reuptake inhibitors (SSRIs). These SSRIs have shown promising results in preclinical trials for treating depression and anxiety disorders. The study demonstrated that the compound's unique structure enabled the synthesis of highly potent and selective SSRIs with improved pharmacokinetic profiles.

Beyond pharmaceutical applications, 4-bromo-N-(4-nitrobenzyl)aniline has also found utility in materials science. Its ability to undergo various chemical transformations makes it a valuable building block for the synthesis of advanced materials with tailored properties. For example, researchers have utilized the compound to develop novel polymers with enhanced mechanical strength and thermal stability. These polymers have potential applications in areas such as electronics, coatings, and composite materials.

In the realm of chemical synthesis, 4-bromo-N-(4-nitrobenzyl)aniline serves as a versatile starting material for a wide range of reactions. Its reactivity can be harnessed to introduce various functional groups or to modify existing ones, making it an essential tool in synthetic organic chemistry. The compound's stability under different reaction conditions allows chemists to perform multi-step syntheses with high yields and selectivity.

The safety profile of 4-bromo-N-(4-nitrobenzyl)aniline is an important consideration for both laboratory use and industrial applications. While it is generally considered safe when handled properly, standard precautions should be taken to avoid exposure to skin or inhalation. It is recommended to work with the compound under a fume hood and to use appropriate personal protective equipment (PPE) such as gloves and safety goggles.

In conclusion, 4-bromo-N-(4-nitrobenzyl)aniline (CAS No. 355814-56-1) is a multifaceted organic compound with significant potential across multiple scientific disciplines. Its unique molecular structure and chemical properties make it an invaluable intermediate in pharmaceutical research, materials science, and synthetic chemistry. As ongoing research continues to uncover new applications and optimizations, this compound is poised to play an increasingly important role in advancing scientific knowledge and technological innovation.

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