Production Method 1

7147-90-2

96385-49-8

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Water

Reference

Application of the Hofmann reaction to the synthesis of heterocyclic compounds. III. Synthesis of 3-alkyl-2,4-diketo-1, 2, 3, 4-tetrahydroquinazolines from N-alkylphthalamides

Spring, F. S.; Woods, J. C., Journal of the Chemical Society, 1945, 625, 625-8

Production Method 2

7147-90-2

96385-49-8

Reaction Conditions

1.1 Reagents: Ammonium hydroxide

Reference

Kinetics and equilibrium in the ammonolysis of substituted phthalimides

McClelland, Robert A.; Seaman, N. Esther; Duff, James M.; Branston, R. E., Canadian Journal of Chemistry, 1985, 63(1), 121-8

4-Chlorophthalamide Raw materials

• 5-chloro-2,3-dihydro-1H-isoindole-1,3-dione

4-Chlorophthalamide Preparation Products

• 4-Chlorophthalamide (96385-49-8)

• 1. An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode
  Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. Killard Analyst, 2008,133, 391-399
• 2. Aggregation-induced emission leading to two distinct emissive species in the solid-state structure of high-dipole organic chromophores?
  Felix Witte,Philipp Rietsch,Nithiya Nirmalananthan-Budau,Florian Weigert,Jan P. G?tze,Ute Resch-Genger,Siegfried Eigler,Beate Paulus Phys. Chem. Chem. Phys., 2021,23, 17521-17529
• 3. An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells?
  Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang Cheng Food Funct., 2020,11, 10635-10644
• 4. An analysis of the WTC fires using CIB correlations and simple modeling
  JGQuintiere
• 5. An investigation into the origin of variations in photovoltaic performance using D–D–π–A and D–A–π–A triphenylimidazole dyes with a copper electrolyte?
  Govind Reddy Mol. Syst. Des. Eng., 2021,6, 779-789

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

Comprehensive Overview of 4-Chlorophthalamide (CAS No. 96385-49-8): Properties, Applications, and Industry Insights

4-Chlorophthalamide (CAS No. 96385-49-8), a specialized organic compound, has garnered significant attention in agrochemical and pharmaceutical research due to its unique molecular structure and functional versatility. This chlorinated derivative of phthalamide features a benzene ring substituted with both a chloro group and an amide moiety, enabling interactions with biological systems and materials. Its systematic IUPAC name, 4-chlorobenzene-1,2-dicarboxamide, reflects its precise chemical configuration, while alternative designations like NSC 348948 highlight its historical use in screening programs.

In modern applications, 4-Chlorophthalamide serves as a key intermediate for synthesizing advanced crop protection agents. Researchers have explored its potential as a precursor for herbicide safeners, which mitigate damage to crops while enhancing weed control efficiency—a critical concern given rising global food demand. The compound’s mechanism of action, involving interference with auxin-like growth regulators, aligns with sustainable agriculture trends seeking low-residue agrochemicals. Analytical studies utilizing HPLC-MS and NMR spectroscopy confirm its stability under physiological pH ranges, supporting formulations for targeted delivery systems.

Environmental considerations surrounding 96385-49-8 have prompted rigorous biodegradability assessments. Recent OECD 301F testing demonstrates moderate persistence in aerobic soils (DT50 = 32–45 days), positioning it favorably compared to traditional chlorinated analogues. This data addresses growing consumer inquiries about eco-friendly chemical alternatives, particularly in the EU where REACH compliance drives innovation. Patent analyses reveal novel applications in photovoltaic materials, where its electron-withdrawing properties enhance organic semiconductor performance—an intersection of chemistry and renewable energy technologies frequently searched in academic databases.

The synthesis of 4-Chlorophthalamide typically proceeds through controlled chlorination of phthalic anhydride derivatives, followed by amidation. Process optimization studies published in Organic Process Research & Development emphasize atom economy improvements, reducing stoichiometric waste by 22% through catalytic amidation techniques. Such advancements respond to industry demands for green chemistry metrics, a trending topic in ESG (Environmental, Social, and Governance) reporting. Supply chain data indicates growing API (Active Pharmaceutical Ingredient) applications, with cGMP manufacturers offering >99.5% purity grades for orphan drug formulations targeting rare metabolic disorders.

Market intelligence platforms note increased searches for "4-Chlorophthalamide suppliers" and "CAS 96385-49-8 price trends," reflecting procurement interest from Asian specialty chemical hubs. Regulatory filings show approved uses in Japan’s positive list system for agricultural additives, while USPTO records disclose its incorporation into biodegradable polymer plasticizers. These diverse applications underscore the compound’s adaptability to circular economy principles—a priority for investors analyzing sustainable chemical portfolios.

From a technical perspective, 96385-49-8 exhibits notable crystallinity (mp 208–210°C) and limited solubility in polar aprotic solvents, necessitating specialized formulation technologies for commercial products. Collaborative research between academic and industrial teams has developed nanocrystalline suspensions to overcome bioavailability challenges, a solution frequently cited in recent drug delivery system patents. Safety assessments classify the compound as non-mutagenic in Ames tests, with LD50 values >2000 mg/kg (oral, rat), supporting its inclusion in low-toxicity chemical inventories.

Emerging studies investigate 4-Chlorophthalamide’s role in enzyme inhibition, particularly against carbonic anhydrase isoforms relevant to glaucoma therapy. This pharmacological potential aligns with PubMed’s rising search terms like "chlorinated amides drug discovery." Concurrently, material scientists utilize its rigid aromatic core to engineer metal-organic frameworks (MOFs) for gas storage—addressing energy sector queries about hydrogen storage materials. Such interdisciplinary applications demonstrate how traditional agrochemical intermediates evolve to meet cutting-edge technological demands.

Quality control protocols for CAS 96385-49-8 emphasize residual solvent monitoring via GC-FID, particularly for DMF and DMAc traces below ICH Q3C limits. Analytical method development papers highlight UHPLC-DAD techniques achieving 0.05% impurity detection, crucial for pharmaceutical grade material. These technical specifications directly respond to frequent purchaser inquiries about "4-Chlorophthalamide analytical standards" and "HPLC purity certificates" observed in chemical database search logs.

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