Cas no 103275-21-4 (3-Bromo-4-(tert-butyl)aniline)

3-Bromo-4-(tert-butyl)aniline structure
3-Bromo-4-(tert-butyl)aniline structure
Product Name:3-Bromo-4-(tert-butyl)aniline
CAS No:103275-21-4
MF:C10H14BrN
MW:228.128861904144
MDL:MFCD09966047
CID:1034989
PubChem ID:423726
Update Time:2025-09-23

3-Bromo-4-(tert-butyl)aniline Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-4-(tert-butyl)aniline
    • 1-tert-Butyl-2-brom-4-amino-benzol
    • 2-Brom-4-amino-1-tert.-butyl-benzol
    • 2-Brom-4-amino-tert-butyl-benzol
    • 3-Brom-4-tert-butyl-anilin
    • 3-bromo-4-tert-butyl-aniline
    • 3-bromo-4-tert-butylphenylamine
    • 3-bromo-4-tert-butyl-phenylamine
    • 4-(tert-butyl)-3-bromophenylamine
    • 4-Amino-2-brom-1-tert-butyl-benzol
    • AC1L9NXM
    • CTK7D6109
    • SBB097244
    • SureCN1684402
    • 3-bromo-4-tert-butylaniline
    • AK130597
    • FCH1396693
    • BC600014
    • AM805780
    • AX8251520
    • ST2401843
    • MFCD09966047
    • CS-0059262
    • DTXSID10329774
    • AKOS016015038
    • 103275-21-4
    • DB-252370
    • A1-10862
    • SCHEMBL1684402
    • SB79606
    • SY103159
    • DS-6730
    • MDL: MFCD09966047
    • Inchi: 1S/C10H14BrN/c1-10(2,3)8-5-4-7(12)6-9(8)11/h4-6H,12H2,1-3H3
    • InChI Key: AXNHKDCJNXKFFT-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C=CC=1C(C)(C)C)N

Computed Properties

  • Exact Mass: 227.03096g/mol
  • Monoisotopic Mass: 227.03096g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 150
  • 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: 3.6
  • Topological Polar Surface Area: 26

3-Bromo-4-(tert-butyl)aniline Security Information

3-Bromo-4-(tert-butyl)aniline Pricemore >>

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3-Bromo-4-(tert-butyl)aniline Related Literature

Additional information on 3-Bromo-4-(tert-butyl)aniline

Research Briefing on 3-Bromo-4-(tert-butyl)aniline (CAS: 103275-21-4) in Chemical Biology and Pharmaceutical Applications

3-Bromo-4-(tert-butyl)aniline (CAS: 103275-21-4) is a halogenated aniline derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a crucial intermediate in the synthesis of various bioactive molecules, including kinase inhibitors, antimicrobial agents, and fluorescent probes. Recent studies have highlighted its role in the development of novel therapeutic candidates and its utility in chemical biology tool development.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of 3-Bromo-4-(tert-butyl)aniline as a key building block in the synthesis of potent and selective JAK2 inhibitors. The researchers utilized this compound to introduce the tert-butyl group, which significantly improved the metabolic stability of the resulting inhibitors while maintaining their target affinity. The study reported IC50 values in the low nanomolar range for several derivatives, suggesting promising therapeutic potential for myeloproliferative disorders.

In the field of antimicrobial research, a recent publication in Bioorganic & Medicinal Chemistry Letters (2024) described the incorporation of 3-Bromo-4-(tert-butyl)aniline into novel quinolone derivatives. These compounds exhibited remarkable activity against drug-resistant Gram-positive bacteria, with MIC values as low as 0.5 μg/mL against MRSA strains. The presence of the bromine atom at the 3-position was found to be critical for maintaining antibacterial activity while the tert-butyl group contributed to improved pharmacokinetic properties.

From a chemical biology perspective, researchers have exploited the reactivity of 3-Bromo-4-(tert-butyl)aniline in various coupling reactions. A 2023 Nature Communications paper detailed its use in Buchwald-Hartwig amination reactions to create fluorescent molecular rotors for viscosity sensing in live cells. The compound's structural features allowed for fine-tuning of photophysical properties while maintaining cell permeability, making it valuable for intracellular microenvironment studies.

The synthetic accessibility of 3-Bromo-4-(tert-butyl)aniline has also been improved through recent methodological advances. A 2024 Organic Process Research & Development report described a scalable, continuous-flow synthesis route that achieved >90% yield with excellent purity (>99.5%). This development addresses previous challenges in large-scale production and makes the compound more accessible for pharmaceutical applications.

Looking forward, the unique structural features of 3-Bromo-4-(tert-butyl)aniline continue to inspire new applications. Current research directions include its incorporation into PROTAC molecules (as evidenced by several recent patent applications) and its use in covalent inhibitor design. The compound's balanced lipophilicity and steric properties make it particularly valuable for these emerging therapeutic modalities.

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