Production Method 1

434-75-3

79455-63-3

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Ethyl acetate ;  8 h, reflux

Reference

Synthesis and biological activities of 2-fluoro-6-chlorobenzoylpyrimidinylthioureas

Xue, Si-Jia; Wang, Jie-Ping, Youji Huaxue, 2003, 23(10), 1162-1164

Production Method 2

434-75-3

79455-63-3

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Acetonitrile ;  2 h, reflux

Reference

Synthesis and bioactivity of N'-tert-butyl-N-substituted acyl(thio)urea derivatives

Xue, Si-Jia; Ke, Shao-Yong; Duan, Li-Ping, Youji Huaxue, 2004, 24(2), 227-230

Production Method 3

434-75-3

79455-63-3

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  1 h, rt

Reference

Discovery of Potent OTUB1/USP8 Dual Inhibitors Targeting Proteostasis in Non-Small-Cell Lung Cancer

Tan, Lingli; Shan, Hengyue; Han, Chao ; Zhang, Zhenfeng; Shen, Jiali; et al, Journal of Medicinal Chemistry, 2022, 65(20), 13645-13659

Production Method 4

434-75-3

79455-63-3

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Toluene ;  3 h, reflux

Reference

Discovery of [1,2,4]triazolo[4,3-a]pyridines as potent Smoothened inhibitors targeting the Hedgehog pathway with improved antitumor activity in vivo

Tian, Nannan; Wu, Huanxian; Zhang, Huiwu; Yang, Danni; Lv, Lin; et al, Bioorganic & Medicinal Chemistry, 2020, 28(16),

2-chloro-6-fluorobenzoyl chloride Raw materials

• 2-chloro-6-fluoro-benzoic acid

2-chloro-6-fluorobenzoyl chloride Preparation Products

• 2-chloro-6-fluorobenzoyl chloride (79455-63-3)

• 1. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
• 2. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
• 3. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 4. Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications
  Partha Laskar,Christine Dufès Nanoscale Adv., 2021,3, 6007-6026
• 5. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341

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

Professional Introduction to 2-Chloro-6-Fluorobenzoyl Chloride (CAS No. 79455-63-3)

2-Chloro-6-fluorobenzoyl chloride, with the chemical formula C?H?ClF?O? and CAS number 79455-63-3, is a highly versatile and significant compound in the field of organic synthesis and pharmaceutical research. This compound belongs to the class of benzoyl chlorides, which are widely recognized for their utility in the synthesis of various bioactive molecules, including pharmaceuticals and agrochemicals. The presence of both chloro and fluoro substituents on the benzene ring imparts unique reactivity and electronic properties, making it a valuable intermediate in multiple synthetic pathways.

The 2-chloro-6-fluorobenzoyl chloride is particularly notable for its role in the development of novel therapeutic agents. In recent years, there has been a growing interest in fluorinated compounds due to their enhanced metabolic stability, improved binding affinity, and increased bioavailability. The chloro group in this molecule acts as a good leaving group, facilitating various nucleophilic substitution reactions, which are crucial in constructing complex molecular architectures. This characteristic has made it a preferred choice for medicinal chemists seeking to develop new drugs with improved pharmacokinetic profiles.

One of the most compelling applications of 2-chloro-6-fluorobenzoyl chloride is in the synthesis of peptide mimetics and protease inhibitors. Peptide-based drugs have gained significant traction in recent decades due to their high specificity and efficacy. However, their susceptibility to enzymatic degradation often limits their therapeutic utility. The introduction of fluorine atoms into peptide mimetics has been shown to enhance their resistance to proteolytic enzymes, thereby prolonging their half-life in vivo. The benzoyl chloride moiety in 2-chloro-6-fluorobenzoyl chloride serves as an effective tool for introducing this protective group, enabling the design of more stable and potent peptide analogs.

Recent advancements in computational chemistry have further highlighted the importance of 2-chloro-6-fluorobenzoyl chloride in drug discovery. Molecular modeling studies have demonstrated that fluorinated benzoyl chlorides can exhibit favorable interactions with biological targets, leading to improved drug-like properties. For instance, studies have shown that the presence of a fluoro group can modulate the electronic distribution around the benzene ring, enhancing binding affinity to enzymes and receptors. This insight has guided the design of novel inhibitors targeting diseases such as cancer, inflammation, and infectious disorders.

In addition to its role in peptide chemistry, 2-chloro-6-fluorobenzoyl chloride has found applications in the synthesis of heterocyclic compounds. Heterocycles are a cornerstone of modern pharmaceuticals, with many drugs containing nitrogen-containing rings exhibiting remarkable biological activity. The compound's reactivity allows for facile introduction of fluorinated benzoyl groups into heterocyclic frameworks, which can then be further functionalized to produce complex scaffolds. Such modifications often lead to compounds with enhanced pharmacological properties, making 2-chloro-6-fluorobenzoyl chloride an indispensable tool in synthetic organic chemistry.

The industrial production of 2-chloro-6-fluorobenzoyl chloride typically involves the chlorination and fluorination of appropriately substituted benzene derivatives. Advances in green chemistry have led to the development of more sustainable methods for these transformations, minimizing waste and reducing environmental impact. For example, catalytic processes using transition metals have been explored as alternatives to traditional halogenation methods. These innovations not only improve efficiency but also align with global efforts to promote sustainable chemical manufacturing.

Another area where 2-chloro-6-fluorobenzoyl chloride has made significant contributions is in materials science. Fluorinated compounds are known for their unique material properties, such as low friction coefficients and high thermal stability. The incorporation of 2-chloro-6-fluorobenzoyl chloride into polymer matrices has been shown to enhance the performance of advanced materials used in electronics, coatings, and aerospace applications. The ability to fine-tune electronic properties through fluorine substitution makes this compound a valuable asset for developing next-generation materials with tailored functionalities.

The future prospects for 2-chloro-6-fluorobenzoyl chloride are promising, with ongoing research exploring its potential in emerging fields such as nanotechnology and biomedicine. Nanoparticles functionalized with fluorinated benzoyl groups have shown promise in targeted drug delivery systems, where they can enhance cellular uptake and reduce off-target effects. Similarly, bioimaging probes incorporating these motifs have demonstrated improved sensitivity and specificity in diagnostic applications. As our understanding of molecular interactions continues to evolve, the utility of 2-chloro-6-fluorobenzoyl chloride is expected to expand even further.

In conclusion, 2-chloro-6-fluorobenzoyl chloride (CAS No. 79455-63-3) is a multifaceted compound with broad applications across pharmaceuticals, materials science, and beyond. Its unique structural features make it an invaluable intermediate for synthesizing bioactive molecules with enhanced pharmacological properties. As research progresses and new methodologies are developed, the importance of this compound will only continue to grow, solidifying its place as a cornerstone of modern chemical synthesis.

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