Cas no 183158-32-9 (Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI))

Boronic acid, (6-hydroxy-1-naphthalenyl)- (9CI), is a naphthalene-based boronic acid derivative featuring a hydroxyl group at the 6-position. This compound is primarily utilized as a versatile intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, owing to its stable boronic acid functionality. The hydroxyl group enhances its solubility in polar solvents and allows for further functionalization, making it valuable in pharmaceutical and materials science applications. Its well-defined structure and reactivity profile ensure consistent performance in forming carbon-carbon bonds. The compound is typically handled under inert conditions to preserve its stability and reactivity. Suitable for research and industrial applications requiring precise boronic acid reagents.
Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI) structure
183158-32-9 structure
Product Name:Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI)
CAS No:183158-32-9
MF:C10H9BO3
MW:187.987663030624
MDL:MFCD18417840
CID:113999
PubChem ID:45116882
Update Time:2025-08-05

Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI) Chemical and Physical Properties

Names and Identifiers

    • Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI)
    • (6-hydroxynaphthalen-1-yl)boronic acid
    • Boronic acid, (6-hydroxy-1-naphthalenyl)- (9CI)
    • starbld0018430
    • DTXSID00668508
    • 183158-32-9
    • 6-HYDROXY-1-NAPHTHALENYLBORONIC ACID
    • SCHEMBL4794960
    • 6-HYDROXYNAPHTHALEN-1-YLBORONIC ACID
    • 6-Hydroxynaphthalene-1-boronic acid
    • G67026
    • MDL: MFCD18417840
    • Inchi: 1S/C10H9BO3/c12-8-4-5-9-7(6-8)2-1-3-10(9)11(13)14/h1-6,12-14H
    • InChI Key: OBNCFKAITIDEMR-UHFFFAOYSA-N
    • SMILES: OC1C=CC2=C(B(O)O)C=CC=C2C=1

Computed Properties

  • Exact Mass: 187.06807
  • Monoisotopic Mass: 188.0644743g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 198
  • 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
  • Surface Charge: 0
  • Tautomer Count: 3
  • XLogP3: nothing
  • Topological Polar Surface Area: 60.7?2

Experimental Properties

  • PSA: 60.69

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Additional information on Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI)

Comprehensive Overview of Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI) (CAS No. 183158-32-9)

Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI), with the CAS number 183158-32-9, is a specialized organic compound that has garnered significant attention in the fields of medicinal chemistry, materials science, and catalysis. This compound belongs to the class of arylboronic acids, which are widely recognized for their versatility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The presence of both a hydroxyl group and a naphthalene ring in its structure enhances its reactivity and potential applications in designing advanced materials and pharmaceuticals.

In recent years, the demand for boronic acid derivatives has surged due to their pivotal role in drug discovery and bioconjugation. Researchers are particularly interested in 183158-32-9 for its potential as a building block in the synthesis of targeted therapeutics, such as protease inhibitors and kinase modulators. Its unique structure allows for selective binding to biomolecules, making it a valuable tool in chemical biology and diagnostic assays. Additionally, the compound's fluorescence properties have sparked interest in bioimaging applications, where it can be used to track cellular processes in real-time.

The synthesis of Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI) typically involves the lithiation-borylation of 6-hydroxy-1-bromonaphthalene, followed by oxidation. This method ensures high purity and yield, which are critical for its use in high-throughput screening and combinatorial chemistry. The compound's stability under physiological conditions further enhances its appeal for biomedical research, where it is often employed as a probe or ligand in studying enzyme mechanisms.

From an industrial perspective, CAS 183158-32-9 is gaining traction in the development of organic electronic materials. Its conjugated aromatic system and boronic acid moiety make it a promising candidate for OLEDs (organic light-emitting diodes) and sensors. The compound's ability to form stable complexes with diols and other Lewis bases also opens doors for its use in molecular recognition systems, such as glucose sensors for diabetes management.

Environmental and safety considerations are paramount when handling Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI). While it is not classified as hazardous under standard regulations, proper storage in a cool, dry place and the use of personal protective equipment (PPE) are recommended to ensure safe laboratory practices. The compound's biodegradability and low toxicity profile align with the growing emphasis on green chemistry principles in industrial applications.

In summary, Boronic acid,(6-hydroxy-1-naphthalenyl)- (9CI) (183158-32-9) is a multifaceted compound with broad utility in pharmaceuticals, materials science, and biotechnology. Its unique structural features and reactivity continue to inspire innovations across multiple disciplines, making it a subject of ongoing research and development. As the scientific community explores new frontiers in precision medicine and smart materials, this compound is poised to play an increasingly vital role.

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