Production Method 1

21739-93-5

18107-18-1

81682-38-4

Reaction Conditions

1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide ;  0 °C; 2 h, rt
1.2 Solvents: Diethyl ether ,  Acetonitrile ;  2 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Ethyl acetate ,  Water ;  rt
1.4 Reagents: Silver acetate Solvents: 1,4-Dioxane ,  Water ;  2 h, 0 °C → 70 °C
1.5 Reagents: Sodium carbonate Solvents: Water

Reference

Phosphodiesters as GPR84 Antagonists for the Treatment of Ulcerative Colitis

Chen, Lin-Hai ; et al, Journal of Medicinal Chemistry, 2022, 65(5), 3991-4006

2-(2-bromo-5-chlorophenyl)acetic acid Raw materials

• 2-Bromo-5-chlorobenzoic acid
• (diazomethyl)trimethylsilane

2-(2-bromo-5-chlorophenyl)acetic acid Preparation Products

• 2-(2-bromo-5-chlorophenyl)acetic acid (81682-38-4)

• 1. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
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• 2. Evolution of dealloying induced strain in nanoporous gold crystals?
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• 3. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 4. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 5. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Chlorobenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Chlorobenzenes

Introduction to 2-(2-bromo-5-chlorophenyl)acetic acid (CAS No. 81682-38-4)

2-(2-bromo-5-chlorophenyl)acetic acid, identified by the Chemical Abstracts Service Number (CAS No.) 81682-38-4, is a significant compound in the realm of pharmaceutical and biochemical research. This compound belongs to the class of substituted aromatic carboxylic acids, characterized by its bromo and chloro substituents on a phenyl ring, which contribute to its unique chemical properties and reactivity. The presence of these halogen atoms enhances its utility in synthetic chemistry, particularly in the development of novel therapeutic agents.

The structural motif of 2-(2-bromo-5-chlorophenyl)acetic acid makes it a versatile intermediate in organic synthesis. Its acetic acid moiety provides a reactive site for further functionalization, enabling the construction of more complex molecules. This feature has been exploited in the synthesis of various pharmacologically active compounds, including kinase inhibitors and anti-inflammatory agents. The bromo and chloro substituents on the phenyl ring further enhance its reactivity, making it a valuable building block for medicinal chemists.

In recent years, there has been growing interest in exploring the pharmacological potential of 2-(2-bromo-5-chlorophenyl)acetic acid and its derivatives. Several studies have highlighted its role in modulating biological pathways associated with inflammation, cancer, and neurodegenerative diseases. For instance, researchers have demonstrated that certain analogs of this compound exhibit potent inhibitory effects on specific enzymes implicated in these conditions. These findings underscore the importance of 2-(2-bromo-5-chlorophenyl)acetic acid as a scaffold for drug discovery.

One notable area of research involves the use of 2-(2-bromo-5-chlorophenyl)acetic acid in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and their dysregulation is often associated with various diseases, particularly cancer. By designing molecules that selectively inhibit aberrant kinase activity, researchers aim to develop targeted therapies with improved efficacy and reduced side effects. The halogenated phenyl ring in 2-(2-bromo-5-chlorophenyl)acetic acid provides a scaffold that can be modified to enhance binding affinity to kinase targets.

Another promising application of 2-(2-bromo-5-chlorophenyl)acetic acid is in the field of anti-inflammatory drug development. Chronic inflammation is a hallmark of many diseases, including rheumatoid arthritis and inflammatory bowel disease. Nonsteroidal anti-inflammatory drugs (NSAIDs) are commonly used to manage inflammation, but their long-term use can lead to adverse effects such as gastrointestinal irritation. Novel anti-inflammatory agents that offer similar efficacy but with improved safety profiles are urgently needed. Compounds derived from 2-(2-bromo-5-chlorophenyl)acetic acid have shown promise in preclinical studies as potential alternatives to traditional NSAIDs.

The synthesis of 2-(2-bromo-5-chlorophenyl)acetic acid typically involves multi-step organic reactions starting from commercially available aromatic precursors. The bromination and chlorination steps are critical and require careful optimization to achieve high yields and selectivity. Advanced synthetic techniques such as palladium-catalyzed cross-coupling reactions have also been employed to introduce additional functional groups onto the phenyl ring, further diversifying the chemical space available for drug discovery.

The pharmacokinetic properties of 2-(2-bromo-5-chlorophenyl)acetic acid and its derivatives are also subjects of intense investigation. Researchers aim to develop compounds that exhibit optimal pharmacokinetic profiles, including good solubility, bioavailability, and metabolic stability. Computational methods such as molecular docking and virtual screening have been instrumental in predicting the binding affinity of candidate compounds to biological targets, thereby accelerating the drug discovery process.

In conclusion, 2-(2-bromo-5-chlorophenyl)acetic acid (CAS No. 81682-38-4) is a multifaceted compound with significant potential in pharmaceutical research. Its unique structural features make it a valuable intermediate for synthesizing novel therapeutic agents targeting various diseases. Ongoing research continues to uncover new applications for this compound, reinforcing its importance in the development of next-generation drugs.

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