Cas no 849236-22-2 (2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)

2-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline is a boronic ester derivative featuring a nitro-substituted aniline core. This compound is primarily utilized as an intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of biaryl structures in pharmaceutical and materials chemistry. The presence of the pinacol boronate ester enhances stability and solubility in organic solvents, facilitating handling and storage. The nitro group offers additional reactivity for further functionalization, making it a versatile building block in synthetic applications. Its well-defined structure and compatibility with palladium-catalyzed reactions make it valuable for constructing complex aromatic systems with precision. Proper handling under inert conditions is recommended due to its sensitivity to moisture.
2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline structure
849236-22-2 structure
Product Name:2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
CAS No:849236-22-2
MF:C12H17BN2O4
MW:264.085383176804
CID:1834712
PubChem ID:59736976
Update Time:2025-10-12

2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Chemical and Physical Properties

Names and Identifiers

    • Benzenamine, 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
    • 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
    • 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine
    • SCHEMBL1065935
    • 849236-22-2
    • 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-nitrobenzenamine
    • QKPMURDGLARQTM-UHFFFAOYSA-N
    • CS-0356869
    • 5-(4,4,5,5-Tetramethyl-I,3,2-dioxaborolan-2-yl)-2-nitrobenzenamine
    • 2-nitro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
    • DA-02375
    • EN300-12599343
    • Z2049761773
    • Inchi: 1S/C12H17BN2O4/c1-11(2)12(3,4)19-13(18-11)8-5-6-10(15(16)17)9(14)7-8/h5-7H,14H2,1-4H3
    • InChI Key: QKPMURDGLARQTM-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CC(=C(C=2)N)[N+](=O)[O-])OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 264.12800
  • Monoisotopic Mass: 264.1281372g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 1
  • Complexity: 353
  • 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
  • Topological Polar Surface Area: 90.3?2

Experimental Properties

  • PSA: 90.30000
  • LogP: 2.58060

2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Pricemore >>

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Additional information on 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Recent Advances in the Study of 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS: 849236-22-2)

The compound 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS: 849236-22-2) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile applications in drug discovery and development. This boronic acid derivative is particularly notable for its role as a key intermediate in Suzuki-Miyaura cross-coupling reactions, which are widely employed in the synthesis of complex organic molecules, including pharmaceuticals. Recent studies have explored its utility in the design of novel therapeutic agents, with a focus on its potential as a building block for targeted drug delivery systems and enzyme inhibitors.

One of the most promising applications of 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline is in the development of proteasome inhibitors. Research published in the Journal of Medicinal Chemistry (2023) highlights its incorporation into bortezomib analogs, which exhibit enhanced selectivity and reduced off-target effects compared to existing treatments. The boronic acid moiety of the compound plays a critical role in binding to the proteasome's active site, thereby inhibiting its function and inducing apoptosis in cancer cells. These findings underscore the compound's potential as a scaffold for next-generation anticancer therapies.

In addition to its therapeutic applications, recent advancements in synthetic methodologies have improved the efficiency of producing 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. A study in Organic Letters (2024) describes a novel one-pot synthesis route that significantly reduces reaction times and improves yields. This methodological innovation is expected to facilitate broader adoption of the compound in both academic and industrial settings, enabling more rapid exploration of its chemical and biological properties.

Furthermore, the compound's utility extends to the field of chemical biology, where it has been employed as a probe for studying enzyme mechanisms. A recent publication in ACS Chemical Biology (2024) details its use in activity-based protein profiling (ABPP) to identify and characterize serine hydrolases in complex biological samples. The nitro group in the aniline moiety allows for subsequent functionalization, making it a versatile tool for labeling and detecting enzyme activity in vivo and in vitro.

Despite these advancements, challenges remain in optimizing the pharmacokinetic properties of derivatives based on 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline. Issues such as poor solubility and metabolic instability have been reported in preclinical studies, necessitating further structural modifications. Ongoing research aims to address these limitations through the introduction of solubilizing groups and the exploration of prodrug strategies, as discussed in a recent review in Bioorganic & Medicinal Chemistry Letters (2024).

In conclusion, 2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS: 849236-22-2) represents a valuable chemical entity with diverse applications in medicinal chemistry and chemical biology. Its role in drug discovery, synthetic methodology, and enzyme profiling continues to expand, driven by recent research breakthroughs. Future studies will likely focus on overcoming current limitations and unlocking its full potential as a therapeutic agent and research tool.

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