2,4-Dichlorobenzaldehyde
[CAS# 874-42-0]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: 2,4-Dichlorobenzaldehyde
• Synonyms: 2,4-DCAD; 2,4-Dichlorobenzaldehyde
• Molecular Formula: C₇H₄Cl₂O
• Molecular Weight: 175.01
• CAS Registry Number: 874-42-0
• EC Number: 212-861-1
• SMILES: C1=CC(=C(C=C1Cl)Cl)C=O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 64-69 °C
• Index of Refraction: 1.601, Calc.^*
• Boiling Point: 233.0±0.0 °C (760 mmHg), Calc.^*, 233 °C
• Flash Point: 100.2±22.3 °C, Calc.^*, 135 °C
• Water solubility: <0.1 g/100 mL at 24 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS09 Danger
• Risk Statements: H314-H318-H411
• Safety Statements: P260-P264-P264+P265-P273-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

2,4-Dichlorobenzaldehyde is an organic compound that has garnered attention in various fields, particularly in pharmaceuticals, agriculture, and chemical synthesis. This compound, with the molecular formula C7H4Cl2O, is characterized by a benzaldehyde functional group attached to a benzene ring that has chlorine substituents at the 2 and 4 positions. The discovery of 2,4-dichlorobenzaldehyde can be traced back to the systematic study of chlorinated aromatic compounds in the late 19th and early 20th centuries. Researchers sought to understand the chemical properties and reactivities of chlorobenzaldehydes, leading to the synthesis of various derivatives, including 2,4-dichlorobenzaldehyde.

The synthesis of 2,4-dichlorobenzaldehyde is typically achieved through the chlorination of benzaldehyde or through the Friedel-Crafts acylation reaction using appropriate chlorinated aromatic compounds. The introduction of chlorine atoms into the benzene ring alters the reactivity of the compound, making it a valuable intermediate in the synthesis of pharmaceuticals and agrochemicals.

In the pharmaceutical industry, 2,4-dichlorobenzaldehyde serves as a key building block for the synthesis of various biologically active compounds. Its versatility allows it to be used in the development of drugs targeting a range of conditions, including anti-inflammatory and antimicrobial applications. The presence of chlorine atoms enhances the lipophilicity and metabolic stability of the resulting compounds, making them more effective in therapeutic contexts.

Additionally, 2,4-dichlorobenzaldehyde is utilized in the synthesis of dyes and pigments. The compound's ability to form stable complexes with metal ions makes it suitable for creating colorants used in textiles, plastics, and other materials. The application of this compound in dye synthesis highlights its importance beyond the pharmaceutical realm, contributing to various industries.

Moreover, in organic synthesis, 2,4-dichlorobenzaldehyde acts as a valuable reagent for the preparation of diverse chemical compounds. It is often involved in nucleophilic addition reactions, where nucleophiles can attack the electrophilic carbon of the aldehyde group, leading to the formation of alcohols or amines. This property makes it an essential component in synthetic routes aimed at producing complex organic molecules.

The environmental impact of chlorinated compounds, including 2,4-dichlorobenzaldehyde, has raised concerns. Regulatory agencies have scrutinized the use and disposal of chlorinated organic compounds due to their potential toxicity and persistence in the environment. Therefore, ongoing research focuses on developing safer alternatives and green chemistry approaches to mitigate these concerns while utilizing the advantageous properties of compounds like 2,4-dichlorobenzaldehyde.

In summary, 2,4-dichlorobenzaldehyde is a significant compound in organic chemistry with diverse applications in pharmaceuticals, agriculture, and chemical synthesis. Its discovery has paved the way for the development of various products that enhance human health and industrial processes. Ongoing research and advancements in synthetic methodologies continue to explore its potential while addressing environmental considerations.

References

2024. New N-amino-5-cyano-6-pyridones as antimicrobial small molecules endowed with DNA gyrase a inhibitory activity: design, one-pot synthesis, biological assessment and in silico insights. BMC Chemistry, 18(1).
DOI: 10.1186/s13065-024-01342-9

2022. Synthesis, in silico molecular docking analysis, pharmacokinetic properties and evaluation of antibacterial and antioxidant activities of fluoroquinolines. BMC Chemistry, 16(1).
DOI: 10.1186/s13065-022-00795-0

2021. Synthesis, antibiotic modifying activity, ADMET study and molecular docking of chalcone (E)-3-(2,4-dichlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one in strains of Staphylococcus aureus carrying MepA efflux pumps. Archives of Microbiology, 204(1).
DOI: 10.1007/s00203-021-02666-z