• 1. Phenolic cyclisation. Part X. Isoquinoline cyclisation under basic conditions
  T. Kametani,K. Kigasawa,M. Hiiragi,H. Ishimaru J. Chem. Soc. C 1971 2632
• 2. Design, eco-friendly synthesis, molecular modeling and anticancer evaluation of thiazol-5(4H)-ones as potential tubulin polymerization inhibitors targeting the colchicine binding site
  Abeer M. El-Naggar,Ibrahim H. Eissa,Amany Belal,Amira A. El-Sayed RSC Adv. 2020 10 2791
• 3. Highly efficient one-pot multi-component synthesis of α-aminophosphonates and bis-α-aminophosphonates catalyzed by heterogeneous reusable silica supported dodecatungstophosphoric acid (DTP/SiO2) at ambient temperature and their antitubercular evaluation against Mycobactrium Tuberculosis
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives
• Pesticide Chemicals Pesticides Disinfectant
• Solvents and Organic Chemicals Organic Compounds Aldehyde/Ketone
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons
• Pesticide Chemicals Pesticide Intermediates
• Pharmaceutical and Biochemical Products Pharmaceutical Intermediates
• Pharmaceutical and Biochemical Products Pharmaceutical Active Ingredients

4-Chlorobenzaldehyde (CAS No. 104-88-1): Chemical Properties, Applications, and Recent Research Developments

4-Chlorobenzaldehyde, with the chemical formula C?H?ClO and CAS number 104-88-1, is an important aromatic aldehyde that has garnered significant attention in the field of organic chemistry and pharmaceutical research. This compound serves as a versatile intermediate in the synthesis of various fine chemicals, pharmaceuticals, and agrochemicals. Its unique structural properties, characterized by the presence of a chloro substituent on a benzaldehyde backbone, make it a valuable building block for further functionalization and derivatization.

The chemical structure of 4-Chlorobenzaldehyde consists of a benzene ring substituted with a formyl group (CHO) at one position and a chlorine atom (Cl) at the para position relative to the formyl group. This arrangement imparts distinct reactivity patterns, allowing for diverse chemical transformations. The aldehyde group (CHO) is highly reactive and participates in condensation reactions, oxidation processes, and reduction to form primary alcohols. Meanwhile, the chloro substituent enhances electrophilic aromatic substitution reactions, making it a preferred precursor for synthesizing more complex aromatic compounds.

In terms of physical properties, 4-Chlorobenzaldehyde is typically found as a colorless to pale yellow liquid with a characteristic almond-like odor. It exhibits moderate solubility in organic solvents such as ethanol, ether, and acetone but has limited solubility in water due to its non-polar nature. These solubility characteristics make it suitable for various applications where solvent-based reactions are required.

The industrial significance of 4-Chlorobenzaldehyde lies in its role as a key intermediate in the synthesis of pharmaceuticals. For instance, it is widely used in the preparation of antihistamines, analgesics, and other therapeutic agents. The chloro group on the benzaldehyde ring facilitates further functionalization through nucleophilic aromatic substitution or directed electrophilic substitution reactions, enabling the construction of more complex molecular architectures.

Recent research has highlighted the utility of 4-Chlorobenzaldehyde in medicinal chemistry. One notable area of investigation involves its use as a precursor for the synthesis of bioactive molecules targeting neurological disorders. Studies have demonstrated its potential in developing novel compounds that interact with specific neurotransmitter receptors. The structural motif present in 4-Chlorobenzaldehyde, particularly the combination of an aldehyde and chloro group, has been shown to enhance binding affinity and selectivity in drug design.

In addition to pharmaceutical applications, 4-Chlorobenzaldehyde plays a crucial role in agrochemical research. It serves as a starting material for synthesizing herbicides and fungicides that exhibit potent activity against various plant pathogens. The reactivity of the aldehyde group allows for modifications that can improve the bioavailability and environmental stability of these agrochemicals.

The synthesis of 4-Chlorobenzaldehyde can be achieved through several routes. One common method involves the chlorination of ortho-hydroxybenzaldehyde using reagents such as phosphorus oxychloride (POCl?). Alternatively, Friedel-Crafts acylation followed by hydrolysis can also yield this compound efficiently. Advances in catalytic processes have further refined these synthetic pathways, improving yields and reducing byproduct formation.

The chemical reactivity of 4-Chlorobenzaldehyde makes it an attractive candidate for exploring new synthetic methodologies. Researchers have been investigating its use in cross-coupling reactions, such as Suzuki-Miyaura coupling, to introduce aryl groups at specific positions on the benzene ring. These transformations have opened up new avenues for constructing heterocyclic compounds with potential pharmaceutical applications.

In conclusion, 4-Chlorobenzaldehyde (CAS No. 104-88-1) is a multifaceted compound with broad utility across multiple industries. Its role as an intermediate in pharmaceutical synthesis underscores its importance in drug development efforts aimed at treating neurological disorders and other health conditions. Furthermore, its applications in agrochemicals highlight its contribution to sustainable agricultural practices. As research continues to uncover new synthetic strategies and applications for this compound, its significance is expected to grow further.

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• 105511-08-8(5-Chloroisophthalaldehyde)
• 214746-56-2(6-chloronaphthalene-2-carbaldehyde)
• 286013-17-0(Benzaldehyde-formyl-13C,4-chloro- (9CI))
• 103426-20-6(3-Chloro-5-methylbenzaldehyde)
• 10203-08-4(3,5-Dichlorobenzaldehyde)
• 139502-80-0(4'-chloro-[1,1'-biphenyl]-3-carbaldehyde)
• 58966-34-0(5-Chloro-2-methylbenzaldehyde)