Cas no 26071-05-6 (4-amino-N-hydroxybenzamide)

4-Amino-N-hydroxybenzamide is a synthetic organic compound featuring both an amino and a hydroxamic acid functional group. Its molecular structure, C?H?N?O?, lends it utility in coordination chemistry and medicinal research, particularly as a chelating agent or intermediate in pharmaceutical synthesis. The presence of the hydroxamic acid moiety enhances its metal-binding affinity, making it relevant for applications in catalysis or metalloenzyme inhibition studies. The amino group further allows for derivatization, broadening its applicability in heterocyclic chemistry. This compound is typically handled under controlled conditions due to its reactivity. Its purity and stability are critical for reproducible results in research settings.
4-amino-N-hydroxybenzamide structure
4-amino-N-hydroxybenzamide structure
Product Name:4-amino-N-hydroxybenzamide
CAS No:26071-05-6
MF:C7H8N2O2
MW:152.150621414185
MDL:MFCD00456218
CID:273096
PubChem ID:245297
Update Time:2025-08-04

4-amino-N-hydroxybenzamide Chemical and Physical Properties

Names and Identifiers

    • Benzamide,4-amino-N-hydroxy-
    • 4-amino-N-hydroxybenzamide
    • BDBM50025840
    • EN300-865620
    • F84195
    • 4-Amino-N-hydroxy-benzamide
    • NSC57117
    • DTXSID90288653
    • NSC-57117
    • 4-Aminobenzohydroxamic Acid
    • CHEMBL155579
    • 26071-05-6
    • 4-aminophenylhydroxamic acid
    • Benzohydroxamic acid, p-amino-
    • SCHEMBL297618
    • DS-009775
    • benzohydroxamic acid, 4-amino-
    • DTXCID90200138
    • MDL: MFCD00456218
    • Inchi: 1S/C7H8N2O2/c8-6-3-1-5(2-4-6)7(10)9-11/h1-4,11H,8H2,(H,9,10)
    • InChI Key: DKGYBSPSUUVQRL-UHFFFAOYSA-N
    • SMILES: O=C(C1C=CC(=CC=1)N)NO

Computed Properties

  • Exact Mass: 152.05864
  • Monoisotopic Mass: 152.058578
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 141
  • 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: _0.4
  • Topological Polar Surface Area: 75.4

Experimental Properties

  • Density: 1.345
  • Boiling Point: °Cat760mmHg
  • Flash Point: °C
  • Refractive Index: 1.645
  • PSA: 75.35

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Additional information on 4-amino-N-hydroxybenzamide

Professional Introduction to 4-amino-N-hydroxybenzamide (CAS No: 26071-05-6)

4-amino-N-hydroxybenzamide is a significant compound in the field of pharmaceutical chemistry, known for its versatile applications in drug development and bioorganic synthesis. This compound, identified by the chemical abstracts service number CAS No: 26071-05-6, has garnered considerable attention due to its structural properties and potential biological activities. The molecule consists of a benzamide core substituted with an amino group at the para position and a hydroxyl group at the ortho position, making it a valuable intermediate in the synthesis of various pharmacologically active agents.

The structural motif of 4-amino-N-hydroxybenzamide is highly conducive to further functionalization, which has been exploited in numerous research endeavors. Its benzamide moiety is a well-known pharmacophore found in many therapeutic agents, contributing to interactions with biological targets such as enzymes and receptors. The presence of both amino and hydroxyl functional groups provides multiple sites for chemical modification, enabling the design of derivatives with enhanced specificity and efficacy.

In recent years, there has been a surge in research focused on developing novel antimicrobial agents to combat rising drug resistance. 4-amino-N-hydroxybenzamide has emerged as a key intermediate in this pursuit. Researchers have demonstrated its utility in synthesizing derivatives that exhibit potent activity against Gram-positive bacteria, including methicillin-resistant *Staphylococcus aureus* (MRSA). The hydroxyl group in particular plays a crucial role in these derivatives, facilitating hydrogen bonding interactions with bacterial targets and enhancing binding affinity.

Moreover, the compound has shown promise in the development of anti-inflammatory agents. Studies have indicated that certain derivatives of 4-amino-N-hydroxybenzamide can modulate inflammatory pathways by inhibiting key enzymes such as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX). These enzymes are pivotal in the production of pro-inflammatory cytokines and mediators, making them attractive targets for therapeutic intervention. The dual functionality of the molecule allows for precise tuning of its pharmacological profile, leading to compounds with improved selectivity and reduced side effects.

The synthesis of 4-amino-N-hydroxybenzamide itself is an intriguing aspect of organic chemistry. Traditional methods often involve multi-step reactions starting from readily available aromatic precursors. However, recent advancements in catalytic processes have enabled more efficient and sustainable routes to this compound. For instance, transition metal-catalyzed cross-coupling reactions have been employed to construct the benzamide core with high yields and minimal byproducts. Such innovations not only streamline the synthesis but also align with green chemistry principles by reducing waste and energy consumption.

Another area where 4-amino-N-hydroxybenzamide has made significant contributions is in the field of material science. Its ability to form stable complexes with metal ions has led to the development of novel materials with applications ranging from catalysis to sensing. These complexes often exhibit enhanced stability and reactivity compared to their free counterparts, making them valuable in industrial processes and analytical techniques.

The potential applications of 4-amino-N-hydroxybenzamide extend beyond pharmaceuticals and materials science. Researchers are exploring its use in agrochemicals, where derivatives can serve as intermediates for herbicides and fungicides. The structural flexibility of this compound allows for the design of molecules that can interact specifically with biological targets in plants, offering a pathway to more effective and environmentally friendly crop protection agents.

In conclusion, 4-amino-N-hydroxybenzamide (CAS No: 26071-05-6) is a multifaceted compound with broad applications across various scientific disciplines. Its unique structural features make it an invaluable building block for synthesizing pharmacologically active agents, particularly those targeting antimicrobial and anti-inflammatory pathways. The ongoing research into its derivatives continues to uncover new possibilities for therapeutic interventions, while advancements in synthetic methodologies enhance both efficiency and sustainability. As our understanding of its properties grows, so too does its potential to contribute to advancements in medicine, materials science, and beyond.

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