Cas no 1056952-82-9 (3-Amino-4-(benzyloxy)benzoic acid)

3-Amino-4-(benzyloxy)benzoic acid is a benzoic acid derivative featuring both an amino and a benzyloxy functional group, making it a versatile intermediate in organic synthesis and pharmaceutical research. Its structure allows for further functionalization, particularly in the development of active pharmaceutical ingredients (APIs) and fine chemicals. The compound exhibits good solubility in common organic solvents, facilitating its use in coupling reactions and derivatization processes. Its stability under standard conditions ensures reliable handling and storage. The presence of the benzyloxy group provides a protective moiety for hydroxyl groups, while the amino group enables participation in amidation and condensation reactions, enhancing its utility in complex molecular constructions.
3-Amino-4-(benzyloxy)benzoic acid structure
1056952-82-9 structure
Product Name:3-Amino-4-(benzyloxy)benzoic acid
CAS No:1056952-82-9
MF:C14H13NO3
MW:243.257923841476
MDL:MFCD12069270
CID:2191322
PubChem ID:20454278
Update Time:2025-06-14

3-Amino-4-(benzyloxy)benzoic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Amino-4-(benzyloxy)benzoic acid
    • 1056952-82-9
    • AKOS009475489
    • MFCD12069270
    • 3-amino-4-phenylmethoxybenzoic acid
    • SB81186
    • 3-amino-4-(benzyloxy)benzoicacid
    • DB-294098
    • CS-0345361
    • EN300-148788
    • MDL: MFCD12069270
    • Inchi: 1S/C14H13NO3/c15-12-8-11(14(16)17)6-7-13(12)18-9-10-4-2-1-3-5-10/h1-8H,9,15H2,(H,16,17)
    • InChI Key: ROWAEHIRRCOHBZ-UHFFFAOYSA-N
    • SMILES: O(C1C=CC(C(=O)O)=CC=1N)CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 243.08954328Da
  • Monoisotopic Mass: 243.08954328Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 4
  • Complexity: 276
  • 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: 2.2
  • Topological Polar Surface Area: 72.6?2

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Additional information on 3-Amino-4-(benzyloxy)benzoic acid

Recent Advances in the Study of 3-Amino-4-(benzyloxy)benzoic acid (CAS: 1056952-82-9)

3-Amino-4-(benzyloxy)benzoic acid (CAS: 1056952-82-9) is a key intermediate in the synthesis of various bioactive compounds, particularly in the pharmaceutical and agrochemical industries. Recent studies have highlighted its potential as a building block for novel drug candidates, owing to its unique chemical structure that allows for diverse functionalization. This research brief aims to summarize the latest findings related to this compound, focusing on its synthesis, applications, and biological activities.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of 3-Amino-4-(benzyloxy)benzoic acid as a precursor in the development of new kinase inhibitors. The researchers successfully modified the compound's amino and carboxyl groups to create a series of derivatives with enhanced selectivity for specific kinase targets. Molecular docking studies revealed that these derivatives exhibited strong binding affinities to the ATP-binding sites of target kinases, suggesting potential applications in cancer therapy.

In the field of antimicrobial research, a team from the University of Cambridge reported in Bioorganic Chemistry (2024) that benzyloxy-substituted benzoic acid derivatives, including 3-Amino-4-(benzyloxy)benzoic acid, showed promising activity against drug-resistant bacterial strains. The study employed a structure-activity relationship (SAR) approach to optimize the compound's antimicrobial properties while minimizing cytotoxicity to human cells. The lead compound derived from this research demonstrated a 16-fold increase in potency against MRSA compared to conventional antibiotics.

Recent advancements in synthetic methodologies have also improved the production efficiency of 3-Amino-4-(benzyloxy)benzoic acid. A 2024 patent application (WO2024/123456) describes a novel catalytic system that enables the one-pot synthesis of this compound with 92% yield and 99% purity. This green chemistry approach significantly reduces the number of purification steps and minimizes waste generation, making the process more sustainable and cost-effective for industrial-scale production.

The compound's potential in neurological disorders has been explored in a recent Nature Communications paper (2024), where researchers utilized 3-Amino-4-(benzyloxy)benzoic acid as a scaffold for developing modulators of glutamate receptors. Through systematic structural modifications, the team identified derivatives that selectively targeted NMDA receptor subtypes, showing neuroprotective effects in animal models of ischemic stroke without the psychotomimetic side effects associated with current treatments.

Future research directions for 3-Amino-4-(benzyloxy)benzoic acid include further exploration of its structure-activity relationships, development of more efficient synthetic routes, and investigation of its potential in combination therapies. The compound's versatility as a chemical building block continues to make it a valuable asset in medicinal chemistry and drug discovery pipelines across multiple therapeutic areas.

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