• 1. CCLXXIII.—Nitrosation of phenols. Part III. Nitrosation of 4-halogeno-o- and -m-cresols and oximation of the 4-halogeno-2 : 5-toluquinones
  Herbert Henry Hodgson,Francis Harry Moore J. Chem. Soc. 1926 129 2036
• 2. Organic chemistry
  J. Chem. Soc. Abstr. 1915 108 i765
• 3. 70. Syntheses in the phenanthrene series. Part II. 7-Methoxy-1-methylphenanthrene and a new route to phenanthrene
  W. F. Short,H. Stromberg,A. E. Wiles J. Chem. Soc. 1936 319
• 4. Synthesis and liquid-crystalline properties of novel laterally connected twins: the influence of the connecting topology and the length of the rigid core
  Jens Andersen,Carsten Tschierske,Siegmar Diele,Dirk Lose J. Mater. Chem. 1996 6 1297

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Meta cresols
• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Cresols Meta cresols
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

Professional Introduction to 4-Bromo-3-methylphenol (CAS No. 14472-14-1)

4-Bromo-3-methylphenol, with the chemical identifier CAS No. 14472-14-1, is a significant compound in the realm of organic chemistry and pharmaceutical research. This aromatic hydroxyl compound, featuring both bromine and methyl substituents, has garnered considerable attention due to its versatile applications in synthetic chemistry and medicinal chemistry. The unique structural properties of 4-Bromo-3-methylphenol make it a valuable intermediate in the synthesis of various pharmacologically active molecules.

The molecular structure of 4-Bromo-3-methylphenol consists of a benzene ring substituted with a hydroxyl group at the 3-position and a bromine atom at the 4-position, along with a methyl group at the 3-position. This configuration imparts distinct reactivity patterns, making it a useful building block for further functionalization. The presence of both electron-withdrawing (bromine) and electron-donating (methyl) groups allows for diverse chemical transformations, including nucleophilic aromatic substitution, electrophilic aromatic substitution, and metal-catalyzed coupling reactions.

In recent years, 4-Bromo-3-methylphenol has been extensively studied for its potential applications in drug development. Its structural motif is found in several bioactive compounds, including antimicrobial agents, anti-inflammatory drugs, and even in the synthesis of more complex molecules such as kinase inhibitors. The bromine atom, in particular, serves as a handle for further derivatization, enabling chemists to introduce additional functional groups or linkages as needed.

One of the most compelling aspects of 4-Bromo-3-methylphenol is its role in the synthesis of heterocyclic compounds. Heterocycles are essential scaffolds in medicinal chemistry due to their prevalence in biologically active natural products. By incorporating CAS No. 14472-14-1 into the synthesis pathway, researchers can efficiently construct nitrogen-containing heterocycles that exhibit enhanced pharmacological properties. For instance, studies have demonstrated its utility in the preparation of quinoline derivatives, which are known for their antimicrobial and antitumor activities.

The pharmaceutical industry has also explored the use of 4-Bromo-3-methylphenol in the development of novel therapeutic agents. Its ability to serve as a precursor for more complex molecules has led to its incorporation into various drug discovery programs. Researchers have leveraged its reactivity to develop inhibitors targeting specific enzymes involved in metabolic pathways relevant to diseases such as cancer and inflammation. The compound's structural features allow for fine-tuning of drug-like properties, including solubility, bioavailability, and metabolic stability.

Beyond pharmaceutical applications, CAS No. 14472-14-1 finds utility in materials science and agrochemical research. Its aromatic nature makes it a candidate for developing advanced materials with specific electronic properties. Additionally, derivatives of this compound have been investigated for their potential as pesticides or herbicides due to their ability to interact with biological targets in plants and pests.

The synthesis of 4-Bromo-3-methylphenol itself is an area of active research. Several methods have been reported for its preparation, ranging from traditional organic synthesis techniques to more modern approaches involving catalytic processes or flow chemistry. These methods often focus on improving yield, purity, and scalability, which are critical factors for industrial applications. Recent advancements have also emphasized greener synthetic routes that minimize waste and reduce environmental impact.

In conclusion, 4-Bromo-3-methylphenol (CAS No. 14472-14-1) is a multifaceted compound with broad applications across multiple scientific disciplines. Its unique structural features make it an invaluable intermediate in pharmaceutical research, enabling the development of novel therapeutic agents with diverse biological activities. Furthermore, its utility in materials science and agrochemicals underscores its importance beyond traditional medicinal chemistry contexts. As research continues to uncover new synthetic strategies and applications, the significance of this compound is expected to grow even further.

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