Production Method 1

95333-95-2

Reaction Conditions

Reference

Preparation of (phenylalkyl)mercaptoimidazole derivatives as dopamine-β-hydroxylase inhibitors and pharmaceuticals containing them

, European Patent Organization, , ,

Production Method 2

95333-95-2

Reaction Conditions

Reference

2-Imidazolethiols

, South Africa, , ,

Production Method 3

923977-11-1

95333-95-2

Reaction Conditions

1.1 Reagents: Water Solvents: Acetonitrile ;  5 min, rt → 120 °C; 0.5 h, 150 psi, 120 °C

Reference

Efficient synthesis of halo indanones via chlorosulfonic acid mediated Friedel-Crafts cyclization of aryl propionic acids and their use in alkylation reactions

Sharma, Anil K.; Subramani, Amutha V.; Gorman, Christopher B., Tetrahedron, 2007, 63(2), 389-395

Production Method 4

90418-21-6

95333-95-2

Reaction Conditions

Reference

Dopamine β-hydroxylase inhibitors

, European Patent Organization, , ,

Production Method 5

103860-22-6

95333-95-2

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  overnight, rt
1.2 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  overnight, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Preparation of benzene fused heterocyclic compounds as autotaxin inhibitors useful as therapeutic agents

, World Intellectual Property Organization, , ,

Production Method 6

90418-21-6

95333-95-2

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Tetrahydrofuran ;  3 h, 50 psi, rt

Reference

Preparation of alkylsulfonylaminocarboxylic acid as prostaglandin agonists

, World Intellectual Property Organization, , ,

Production Method 7

95333-95-2

Reaction Conditions

Reference

Multisubstrate inhibitors of dopamine β-hydroxylase. 2. Structure-activity relationships at the phenethylamine binding site

Kruse, Lawrence I.; Kaiser, Carl; DeWolf, Walter E. Jr.; Frazee, James S.; Ross, Stephen T.; et al, Journal of Medicinal Chemistry, 1987, 30(3), 486-94

Production Method 8

95333-95-2

Reaction Conditions

Reference

Dopamine-β-hydroxylase inhibitors

, European Patent Organization, , ,

3-(3,5-Dichlorophenyl)propanoic acid Raw materials

• Ethyl 3-(3,5-dichlorophenyl)prop-2-enoate
• 2-Propenoic acid,3-(3,5-dichlorophenyl)-
• 1,3-Dioxane-4,6-dione, 5-[(3,5-dichlorophenyl)methyl]-2,2-dimethyl-

3-(3,5-Dichlorophenyl)propanoic acid Preparation Products

• 3-(3,5-Dichlorophenyl)propanoic acid (95333-95-2)

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• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Phenylpropanoic acids Phenylpropanoic acids
• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Phenylpropanoic acids

3-(3,5-Dichlorophenyl)propanoic Acid (CAS No. 95333-95-2): Properties, Applications, and Market Insights

3-(3,5-Dichlorophenyl)propanoic acid (CAS No. 95333-95-2) is a specialized organic compound that has garnered significant attention in the fields of pharmaceuticals, agrochemicals, and material science. This compound, characterized by its dichlorophenyl moiety and propanoic acid functional group, exhibits unique chemical properties that make it valuable for various industrial and research applications. In this comprehensive overview, we delve into its molecular structure, synthesis methods, applications, and emerging trends in the market.

The molecular formula of 3-(3,5-Dichlorophenyl)propanoic acid is C₉H₈Cl₂O₂, with a molecular weight of 219.06 g/mol. Its structure features a phenyl ring substituted with two chlorine atoms at the 3 and 5 positions, attached to a three-carbon propanoic acid chain. This configuration imparts both lipophilic and acidic characteristics, making it a versatile intermediate in organic synthesis. Researchers often highlight its role in the development of bioactive molecules, particularly in the design of enzyme inhibitors and receptor modulators.

One of the most prominent applications of 3-(3,5-Dichlorophenyl)propanoic acid is in the pharmaceutical industry. Its structural motif is frequently incorporated into drug candidates targeting inflammatory diseases and metabolic disorders. For instance, derivatives of this compound have shown promise as PPAR (Peroxisome Proliferator-Activated Receptor) agonists, which are critical in regulating glucose and lipid metabolism. With the rising global prevalence of diabetes and obesity, the demand for novel metabolic modulators has surged, positioning this compound as a key player in drug discovery pipelines.

In agrochemicals, 3-(3,5-Dichlorophenyl)propanoic acid serves as a precursor for the synthesis of herbicides and fungicides. The dichlorophenyl group enhances the compound's ability to disrupt microbial and plant cell membranes, making it effective in crop protection. As sustainable agriculture gains traction, researchers are exploring eco-friendly derivatives of this compound to minimize environmental impact while maintaining efficacy. This aligns with the growing consumer demand for green chemistry solutions in farming practices.

The synthesis of 3-(3,5-Dichlorophenyl)propanoic acid typically involves the Friedel-Crafts acylation of 1,3-dichlorobenzene followed by reduction and oxidation steps. Recent advancements in catalytic methods have improved the yield and purity of this compound, addressing scalability challenges for industrial production. Innovations such as flow chemistry and microwave-assisted synthesis are being explored to optimize its manufacturing process, reflecting the broader trend toward process intensification in chemical industries.

From a market perspective, the demand for 3-(3,5-Dichlorophenyl)propanoic acid is driven by its multifaceted applications. Pharmaceutical companies are investing heavily in small molecule therapeutics, while agrochemical firms seek novel active ingredients to combat resistant pests and pathogens. Additionally, the compound's potential in material science, such as polymer modification and corrosion inhibition, is being investigated, further expanding its commercial viability. Market analysts project steady growth for this compound, particularly in regions with robust pharmaceutical and agricultural sectors.

Environmental and regulatory considerations are also shaping the future of 3-(3,5-Dichlorophenyl)propanoic acid. Regulatory bodies emphasize the need for thorough toxicological assessments and biodegradability studies to ensure safe usage. Researchers are responding by developing greener synthetic routes and evaluating the compound's environmental fate. These efforts resonate with the global push toward sustainable chemistry and responsible innovation.

In conclusion, 3-(3,5-Dichlorophenyl)propanoic acid (CAS No. 95333-95-2) is a compound of significant scientific and industrial importance. Its unique properties and broad applicability make it a valuable asset in pharmaceuticals, agrochemicals, and beyond. As research continues to uncover new uses and improve synthesis methods, this compound is poised to play a pivotal role in addressing some of the most pressing challenges in health and agriculture. For researchers and industry professionals, staying abreast of the latest developments in dichlorophenyl derivatives and propanoic acid-based compounds is essential to leveraging their full potential.

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