Cas no 850568-07-9 (2-Borono-5-chlorobenzoic acid)

2-Borono-5-chlorobenzoic acid is a boronic acid derivative with the molecular formula C?H?BClO?. This compound features a boronic acid group (–B(OH)?) and a carboxylic acid (–COOH) functionality, making it a versatile intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. The presence of the chloro substituent enhances its reactivity and selectivity in palladium-catalyzed transformations. Its stability under standard conditions and compatibility with various reaction conditions make it a valuable building block for pharmaceutical and agrochemical applications. The compound is typically used in the preparation of biaryl structures, contributing to the development of complex organic molecules. Proper handling and storage are recommended to maintain its integrity.
2-Borono-5-chlorobenzoic acid structure
2-Borono-5-chlorobenzoic acid structure
Product Name:2-Borono-5-chlorobenzoic acid
CAS No:850568-07-9
MF:C7H6BClO4
MW:200.38414144516
MDL:MFCD06659869
CID:720003
PubChem ID:23005367
Update Time:2025-10-25

2-Borono-5-chlorobenzoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Borono-5-chlorobenzoic acid
    • 2-Carboxy-4-chlorobenzeneboronic acid
    • 2-Carboxy-4-chlorophenylboronic acid
    • Benzoic acid,2-borono-5-chloro- (9CI)
    • 5-chloro-2-(dihydroxyboranyl)benzoic acid
    • OR1202
    • FCH1326828
    • AB26513
    • (2-Carboxy-4-chloro)benzeneboronic acid
    • AX8044163
    • 5-chloranyl-2-(dihydroxyboranyl)benzoic acid
    • X2401
    • 2-Carboxy-4-chlorobenzeneboronic acid, AldrichCPR
    • A
    • 2-Borono-5-chlorobenzoicacid
    • AKOS004113829
    • DTXSID70629641
    • 850568-07-9
    • SCHEMBL9937971
    • CS-0174038
    • AS-55277
    • D93222
    • XH0416
    • MFCD06659869
    • MDL: MFCD06659869
    • Inchi: 1S/C7H6BClO4/c9-4-1-2-6(8(12)13)5(3-4)7(10)11/h1-3,12-13H,(H,10,11)
    • InChI Key: RENDEFHQQIYNJL-UHFFFAOYSA-N
    • SMILES: ClC1C=CC(B(O)O)=C(C(=O)O)C=1

Computed Properties

  • Exact Mass: 200.00500
  • Monoisotopic Mass: 200.005
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 199
  • 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: 77.8

Experimental Properties

  • Density: 1.552
  • Melting Point: 300
  • Boiling Point: 423.797°C at 760 mmHg
  • Flash Point: 210.105°C
  • Refractive Index: 1.604
  • PSA: 77.76000
  • LogP: -0.28200

2-Borono-5-chlorobenzoic acid Security Information

  • Hazard Statement: Irritant/Keep Cold
  • Hazard Category Code: 41
  • Safety Instruction: 26-39
  • Hazardous Material Identification: Xi
  • Storage Condition:Keep cold

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Additional information on 2-Borono-5-chlorobenzoic acid

Introduction to 2-Borono-5-chlorobenzoic acid (CAS No. 850568-07-9)

2-Borono-5-chlorobenzoic acid, with the chemical formula C?H?BClO?, is a versatile intermediate in organic synthesis and pharmaceutical research. This compound has garnered significant attention in the scientific community due to its unique structural properties and potential applications in drug development. The presence of both a boronic acid group and a chloro substituent makes it a valuable building block for constructing more complex molecules, particularly in the synthesis of boron-containing heterocycles and bioactive compounds.

The CAS number 850568-07-9 provides a unique identifier for this compound, ensuring consistency and accuracy in scientific literature and industrial applications. As a key intermediate, 2-Borono-5-chlorobenzoic acid plays a crucial role in the development of novel therapeutic agents. Its reactivity allows for the formation of stable boronate esters, which are widely used in pharmaceuticals, particularly in targeted cancer therapies such as boron neutron capture therapy (BNCT). This approach leverages the ability of boronated compounds to selectively accumulate in tumor tissues, enhancing the efficacy of radiation treatment while minimizing damage to healthy cells.

Recent advancements in medicinal chemistry have highlighted the importance of 2-Borono-5-chlorobenzoic acid in the design of small-molecule inhibitors. Researchers have demonstrated its utility in synthesizing potent inhibitors targeting various biological pathways, including kinases and other enzymes involved in metabolic disorders. The boronic acid moiety facilitates coordination with metal ions, which is often exploited in catalytic systems to improve reaction yields and selectivity. This property makes it particularly useful in cross-coupling reactions, such as Suzuki-Miyaura couplings, where it serves as a precursor for constructing biaryl structures.

In addition to its role in drug discovery, 2-Borono-5-chlorobenzoic acid has been explored for its potential applications in materials science. The combination of electronic and steric effects from the boronic acid and chloro groups allows for fine-tuning of material properties, making it suitable for developing organic electronic components. For instance, derivatives of this compound have been investigated as precursors for conductive polymers and organic semiconductors, which are essential for flexible electronics and optoelectronic devices.

The synthesis of 2-Borono-5-chlorobenzoic acid typically involves multi-step organic transformations, starting from readily available benzoic acid derivatives. Advanced synthetic methodologies have been developed to enhance yield and purity, ensuring that researchers can obtain high-quality material for their studies. Techniques such as halogenation followed by boronation are commonly employed, with careful optimization to minimize side reactions. The growing demand for this compound underscores its significance in both academic research and industrial applications.

One notable application of 2-Borono-5-chlorobenzoic acid is in the field of protease inhibition. Proteases are enzymes that play critical roles in various biological processes, including inflammation and cancer progression. By designing molecules that mimic the structure of natural substrates but incorporate pharmacophores like the boronic acid group, researchers can develop selective protease inhibitors. These inhibitors have shown promise in preclinical studies as potential treatments for diseases such as rheumatoid arthritis and certain types of cancer.

The structural flexibility of 2-Borono-5-chlorobenzoic acid also allows it to serve as a scaffold for drug design targeting neurological disorders. For example, modifications at the benzylic position can introduce functional groups that interact with specific neurotransmitter receptors or ion channels. Such interactions may lead to the development of novel therapeutics for conditions like Alzheimer's disease or Parkinson's disease, where modulation of neuronal activity is crucial.

Recent studies have also explored the use of 2-Borono-5-chlorobenzoic acid in combinatorial chemistry approaches. By generating libraries of derivatives through automated synthesis techniques, researchers can rapidly screen large numbers of compounds for biological activity. This high-throughput screening has accelerated the discovery process for new drug candidates, enabling more efficient translation from bench to bedside.

The environmental impact of synthesizing and handling 2-Borono-5-chlorobenzoic acid is another area of growing interest. Efforts are being made to develop greener synthetic routes that minimize waste and reduce energy consumption. These sustainable practices align with broader trends in pharmaceutical manufacturing aimed at improving efficiency while reducing ecological footprints.

In conclusion, 2-Borono-5-chlorobenzoic acid (CAS No. 850568-07-9) is a multifaceted compound with significant potential across multiple scientific disciplines. Its unique structural features make it an invaluable tool for synthetic chemists, pharmacologists, and materials scientists alike. As research continues to uncover new applications for this intermediate, its importance is likely to grow further, driving innovation in both academic laboratories and industrial settings.

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