3,5-Dichlorobenzaldehyde is an organic compound that is a derivative of benzaldehyde. It is a colourless liquid with a pungent odour and is used as a precursor for a variety of chemicals, including dyes, fragrances, and pharmaceuticals.
CAT No: 10-101-233
CAS No:10203-08-4
Synonyms/Alias:3,5-Dichlorobenzaldehyde;10203-08-4;Benzaldehyde, 3,5-dichloro-;3,5-Dichloro-benzaldehyde;M74YU7SE79;EINECS 233-499-0;NSC 109095;NSC-109095;UNII-M74YU7SE79;DTXSID2064997;2,6-DICHLORO-4-BENZALDEHYDE;MFCD00003352;NSC109095;3,5-dichlorobezaldehyde;Benzaldehyde,5-dichloro-;SCHEMBL42392;CHEMBL4577243;DTXCID6032699;3,5-Dichlorobenzaldehyde, 97%;AKOS004905911;AB00316;CS-W017471;PS-6064;AC-23850;D2012;NS00023101;EN300-45020;F2191-0162;Z452409804;
3,5-Dichlorobenzaldehyde is an aromatic aldehyde featuring two chlorine atoms substituted at the 3 and 5 positions of the benzene ring. As a halogenated benzaldehyde, it is recognized for its unique electronic properties and reactivity, which make it a valuable intermediate in organic synthesis and chemical research. The compound's electron-withdrawing dichloro substituents confer distinct reactivity patterns, enabling its use in the construction of more complex molecules, investigation of reaction mechanisms, and development of functionalized materials. Its structural motif is relevant in various domains, including analytical chemistry, material science, and the synthesis of heterocyclic compounds, underscoring its significance in both academic and industrial research settings.
Synthetic intermediate: 3,5-Dichlorobenzaldehyde serves as an important building block in the synthesis of diverse organic molecules. Its aldehyde functional group readily participates in condensation reactions, such as the formation of Schiff bases, oximes, and hydrazones, facilitating the generation of structurally varied intermediates. The dichloro substitution pattern enhances selectivity in electrophilic aromatic substitution and cross-coupling reactions, making it a versatile starting material for the preparation of pharmaceuticals, agrochemicals, and specialty chemicals within research and development laboratories.
Heterocyclic compound synthesis: The reactivity of this aromatic aldehyde is exploited in the construction of heterocyclic frameworks, particularly those containing nitrogen or oxygen atoms. By acting as a key precursor in cyclization reactions, it enables the formation of benzoxazoles, benzothiazoles, and related heterocycles, which are of significant interest in medicinal chemistry, materials science, and chemical biology. The presence of electron-withdrawing chlorine atoms modulates the reactivity, allowing for controlled synthesis and functionalization of these heterocyclic systems.
Analytical chemistry applications: In analytical laboratories, 3,5-dichlorobenzaldehyde is employed as a derivatization reagent to facilitate the detection, quantification, or separation of primary amines and other nucleophilic analytes. Through the formation of imines or related derivatives, it enhances the sensitivity and selectivity of chromatographic and spectroscopic analyses. This utility is particularly valuable in complex sample matrices, where precise identification and measurement of trace compounds are critical for method development and validation.
Material science research: The dichlorinated aromatic scaffold of this compound is leveraged in the development of advanced materials, including functional polymers, resins, and organic electronic components. Its incorporation into polymer backbones or as a crosslinking agent imparts desirable physical and chemical properties, such as increased thermal stability, altered solubility, and enhanced electronic characteristics. Research in this area focuses on tailoring material properties for specific applications in coatings, sensors, and electronic devices.
Mechanistic studies in organic chemistry: Owing to its well-defined structure and predictable reactivity, 3,5-dichlorobenzaldehyde is frequently used as a model substrate for mechanistic investigations. Researchers utilize it to probe the effects of halogen substitution on reaction pathways, kinetics, and selectivity in various organic transformations. These studies contribute to a deeper understanding of structure-activity relationships and inform the rational design of new synthetic methodologies, thereby advancing the field of organic synthesis.
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