3-Chlorocinnamaldehyde (CAS 56578-37-1): Synthetic Applications and Research Profile
3-Chlorocinnamaldehyde (CAS:
56578-37-1), (E)-3-(3-chlorophenyl)prop-2-enal,
characterized by the molecular formula C9H7ClO and a molecular weight of 166.6 g/mol. As a structural
derivative of cinnamaldehyde, the substitution of a chlorine atom at the
meta-position of the phenyl ring significantly alters its electronic profile,
making it a highly sought-after intermediate in medicinal chemistry, materials
science, and fine chemical synthesis.
At finetech
Industry limited, we provide high-purity 3-Chlorocinnamaldehyde
specifically curated for advanced laboratory research and industrial scaling.
Core Applications in Chemical Research
1. Building Block for Heterocyclic
Synthesis
3-Chlorocinnamaldehyde serves as a
primary precursor for the construction of diverse heterocyclic frameworks. The
presence of the reactive aldehyde group and the conjugated double bond allows
for various cyclization reactions. Research indicates its utility in
synthesizing substituted quinolines and pyridines, which are foundational
structures in pharmacological agents.
·
Key Reaction:
The Friedländer synthesis or Hantzsch-type reactions often utilize chlorinated
cinnamaldehydes to introduce specific regioselectivity in the resulting
polycyclic compounds.
2. Intermediate in Medicinal Chemistry
The meta-chloro substitution is often a
strategic choice in drug design to enhance metabolic stability or increase
lipophilicity. 3-Chlorocinnamaldehyde is frequently employed in the synthesis
of:
·
Antifungal Agents: Derivatives of cinnamaldehydes have shown significant inhibitory
effects against various fungal strains by interfering with cell wall synthesis.
·
Enzyme Inhibitors: Its derivatives are studied for their potential in inhibiting beta-HSD1
or as Michael acceptors in covalent bonding with specific protein targets.
3. Catalyst and Ligand Development
In organometallic chemistry,
3-Chlorocinnamaldehyde is used to synthesize specialized ligands. The
electron-withdrawing nature of the chlorine atom influences the coordination
chemistry of the resulting Schiff bases when reacted with primary amines.
Academic References and Literature
Context
To support rigorous academic and
industrial research, the following literature highlights the chemical behavior
and utility of related cinnamaldehyde derivatives:
·
On Reactivity: Journal of
Organic Chemistry – Studies on the 1,4-addition (Michael addition) to alpha,beta-unsaturated
aldehydes emphasize how aryl substitutions (like the 3-chloro group) affect the
electrophilicity of the beta-carbon.
·
On Biological Activity: Bioorganic
& Medicinal Chemistry – Documentation regarding the antimicrobial
properties of substituted cinnamaldehydes suggests that chloro-derivatives
often exhibit enhanced potency compared to unsubstituted counterparts.
·
On Synthetic Methodologies: Tetrahedron
Letters – Various reports detail the use of 3-Chlorocinnamaldehyde in the
synthesis of cinnamyl alcohols and acids via reduction or oxidation processes,
crucial for flavor and fragrance chemistry.
Technical Specifications (Finetech
Industry limited)
|
Property |
Value |
|
Chemical
Name |
3-Chlorocinnamaldehyde |
|
CAS Number |
56578-37-1 |
|
Molecular
Formula |
C9H7ClO |
|
Molecular
Weight |
166.6 |
|
Purity
(GC/HPLC) |
95% |
|
Appearance |
yellow solid
|
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56578-37-1, finetech Industry limited ensures a streamlined supply chain
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