Production Method 1

118-90-1

79669-49-1

76006-33-2

Reaction Conditions

1.1 Reagents: Iron chloride (FeCl3) ,  Bromine ;  0 °C

Reference

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety

Saint-Louis, Carl Jacky; et al, Organic & Biomolecular Chemistry, 2017, 15(48), 10172-10183

Production Method 2

118-90-1

79669-49-1

76006-33-2

Reaction Conditions

1.1 Reagents: Iron ,  Bromine ;  10 min, 0 °C
1.2 20 min, 0 °C; 0 °C → rt; 25.5 h, rt

Reference

Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

Lartia, Remy; et al, Journal of Organic Chemistry, 2008, 73(5), 1732-1744

Production Method 3

79669-49-1

79669-49-1

118-90-1

Reaction Conditions

1.1 Solvents: Acetonitrile ,  Water ;  overnight, pH 9.5, rt
1.2 Reagents: Ethanol
1.3 Reagents: Molybdenum hexacarbonyl ,  Cesium hydroxide Catalysts: Palladate(1-), [2′-(amino-κN)[1,1′-biphenyl]-2-yl-κC]chloro[2′-(dicyclohexylphos… Solvents: 1-Methoxy-2-propanol ,  Water ;  15 h, 80 °C

Reference

Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis

Li, Jian-Yuan; et al, Bioconjugate Chemistry, 2019, 30(8), 2209-2215

5-Bromo-2-methylbenzoic acid Raw materials

• O-Toluic acid
• 5-Bromo-2-methylbenzoic acid

5-Bromo-2-methylbenzoic acid Preparation Products

• O-Toluic acid (118-90-1)
• 5-Bromo-2-methylbenzoic acid (79669-49-1)
• 3-bromo-2-methyl-benzoic acid (76006-33-2)

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• 2. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 3. Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe?
  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161
• 4. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 5. Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples?
  Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Halobenzoic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to 5-Bromo-2-methylbenzoic acid (CAS No. 79669-49-1)

5-Bromo-2-methylbenzoic acid, identified by the Chemical Abstracts Service Number (CAS No.) 79669-49-1, is a significant compound in the realm of organic chemistry and pharmaceutical research. This aromatic carboxylic acid derivative features a bromine substituent at the 5-position and a methyl group at the 2-position of the benzene ring, making it a versatile intermediate in synthetic chemistry and a potential candidate for various biological applications.

The structural configuration of 5-Bromo-2-methylbenzoic acid imparts unique chemical properties that make it valuable in multiple domains. The presence of both bromine and methyl groups enhances its reactivity, allowing for further functionalization through cross-coupling reactions, nucleophilic substitutions, and other synthetic transformations. These attributes have positioned this compound as a key building block in the development of more complex molecules, particularly in medicinal chemistry.

In recent years, the pharmaceutical industry has shown increasing interest in aromatic compounds due to their broad spectrum of biological activities. 5-Bromo-2-methylbenzoic acid has been explored as a precursor in the synthesis of novel drug candidates targeting various diseases. Its benzene core is a common motif in many pharmacophores, and modifications at the 2- and 5-positions can fine-tune interactions with biological targets, such as enzymes and receptors.

One of the most compelling areas of research involving 5-Bromo-2-methylbenzoic acid is its application in the development of anticancer agents. Brominated aromatic compounds have demonstrated efficacy in disrupting cancer cell proliferation by inhibiting key signaling pathways. Studies have indicated that derivatives of benzoic acid, including 5-Bromo-2-methylbenzoic acid, can modulate the activity of enzymes like tyrosine kinases, which are overexpressed in many malignancies. The bromine atom, in particular, serves as a handle for further derivatization, enabling the creation of highly specific inhibitors.

Moreover, 5-Bromo-2-methylbenzoic acid has been investigated for its potential antimicrobial properties. The structural features of this compound allow it to interact with bacterial cell walls and membranes, disrupting essential cellular processes. Research has highlighted its efficacy against Gram-positive bacteria, making it a promising candidate for developing new antibiotics or antibiotic adjuvants. The combination of bromine and methyl groups enhances its binding affinity to bacterial targets while minimizing toxicity to human cells.

The synthesis of 5-Bromo-2-methylbenzoic acid typically involves bromination and methylation reactions starting from commercially available benzoic acid derivatives. Advanced synthetic methodologies have been developed to achieve high yields and purity, ensuring that researchers can reliably incorporate this compound into their studies. Techniques such as palladium-catalyzed cross-coupling reactions have further expanded the synthetic possibilities, allowing for the introduction of additional functional groups with precision.

Recent advancements in computational chemistry have also contributed to the understanding of 5-Bromo-2-methylbenzoic acid's reactivity and mechanism of action. Molecular modeling studies have predicted how this compound interacts with biological targets at an atomic level, providing insights into its potential therapeutic applications. These computational approaches complement experimental work by offering rapid screening of derivatives with optimized properties.

In conclusion, 5-Bromo-2-methylbenzoic acid (CAS No. 79669-49-1) represents a fascinating compound with significant implications in pharmaceutical research and organic synthesis. Its unique structural features enable diverse applications, from anticancer drug development to antimicrobial agents. As research continues to uncover new possibilities for this compound, its role in advancing medical science is poised to grow even further.

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