3,5-Dichloro-4-[(1E)-3-ethoxy-2-methyl-3-oxo-1-propen-1-yl]benzoic acid
[CAS# 1110767-89-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
• Name: 3,5-Dichloro-4-[(1E)-3-ethoxy-2-methyl-3-oxo-1-propen-1-yl]benzoic acid
• Synonyms: (E)-3,5-Dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-en-1-yl)benzoic acid
• Molecular Formula: C₁₃H₁₂Cl₂O₄
• Molecular Weight: 303.14
• CAS Registry Number: 1110767-89-9
• SMILES: CCOC(=O)/C(=C/C1=C(C=C(C=C1Cl)C(=O)O)Cl)/C

Properties

• Solubility: Practically insoluble (0.022 g/L) (25 °C), Calc.^*
• Density: 1.380±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.593, Calc.^*
• Boiling Point: 442.1±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 221.2±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

3,5-Dichloro-4-[(1E)-3-ethoxy-2-methyl-3-oxo-1-propen-1-yl]benzoic acid is a synthetically derived compound of significant interest in the fields of agrochemistry and pharmaceutical research. Its molecular structure features a dichlorinated aromatic ring attached to a conjugated propenyl chain with an ethoxy group, which grants the molecule unique chemical and biological properties. The synthesis of this compound arose from efforts to develop functionalized benzoic acid derivatives with enhanced activity profiles.

The discovery of 3,5-dichloro-4-[(1E)-3-ethoxy-2-methyl-3-oxo-1-propen-1-yl]benzoic acid is linked to research into herbicidal agents. Benzoic acid derivatives have long been recognized for their potential to inhibit plant growth by targeting specific metabolic pathways. The dichloro substitutions on the aromatic ring increase the molecule’s electron-withdrawing properties, making it more reactive and stable in various environments. The conjugated side chain with a carbonyl group introduces additional binding potential with biological targets, enhancing the molecule's ability to interfere with plant enzyme functions.

In agricultural applications, this compound is being explored as a selective herbicide. Its mechanism of action involves the disruption of key biosynthetic processes in broadleaf weeds, which hampers their growth and proliferation. The structural features allow it to act as a Michael acceptor, making it effective at inhibiting enzymes critical for plant development. This selectivity offers potential advantages in reducing harm to non-target plant species and improving crop yields.

Pharmaceutical research has also investigated the properties of 3,5-dichloro-4-[(1E)-3-ethoxy-2-methyl-3-oxo-1-propen-1-yl]benzoic acid. The benzoic acid framework, combined with the electron-withdrawing chlorine atoms and the α,β-unsaturated carbonyl group, provides opportunities for interactions with proteins and receptors. Researchers are evaluating its potential as a scaffold for developing anti-inflammatory or antimicrobial agents. Structural modifications of this compound have shown promise in enhancing bioactivity, stability, and selectivity toward specific biological targets.

The compound's synthetic versatility makes it valuable for further chemical derivatization. The reactive sites on the molecule enable chemists to design analogs with tailored properties, which can be applied in both agrochemical and pharmaceutical domains. The presence of the propenyl chain and ethoxy group allows for fine-tuning of its lipophilicity and reactivity, supporting the development of more effective compounds for specialized applications.

Ongoing studies continue to explore the full range of applications and potential optimizations for 3,5-dichloro-4-[(1E)-3-ethoxy-2-methyl-3-oxo-1-propen-1-yl]benzoic acid. Its discovery underscores the importance of structural design in achieving desired chemical and biological functions, offering a foundation for innovations in herbicide development and therapeutic research.

References

2019. Lusutrombopag. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-12-0091