2,6-Dimethoxybenzoquinone (CAS 530-55-2) is a naturally occurring, methoxy-functionalized quinone derivative commonly found in various plants and fungal species. This compound serves as a versatile building block in organic synthesis, particularly for constructing complex heterocyclic systems and functionalized aromatic structures, leveraging its electron-deficient quinone core as a reactive handle. Its significance extends into biological contexts, where it demonstrates notable bioactive properties, including antimicrobial, antioxidant, and potential antitumor activities, making it a compound of interest in medicinal chemistry and phytochemical research.
Name :
2,6-DimethoxybenzoquinoneCAS No. :
530-55-2MF :
C₈H₈O₄MW :
168.15Purity :
99%Appearance :
Yellow powder or crystalline solidStorage Condition :
Stable under normal conditions but sensitive to light and oxidizing agentsBasic Information
Chemical Name: 2,6-Dimethoxybenzoquinone
CAS Number: 530-55-2
Molecular Formula: C₈H₈O₄
Molecular Weight: 168.15 g/mol
EINECS Number: 208-484-7
Synonyms:
2,6-Dimethoxy-1,4-benzoquinone
2,6-Dimethoxy-p-benzoquinone
2,6-Dimethoxybenzo-1,4-quinone
Physical and Chemical Properties
Appearance: Yellow powder or crystalline solid .
Melting Point: 253–257°C (decomposition) .
Boiling Point: Not well-defined (sublimes at ~175–180°C under reduced pressure) .
Density: ~1.30 g/cm³ (estimated) .
Solubility:
Slightly soluble in ethanol, ether, and DMSO .
Insoluble in water.
Stability: Stable under normal conditions but sensitive to light and oxidizing agents .
Key Applications
Organic Synthesis:
Intermediate for synthesizing 2-aryl-3,5-dimethoxy-1,4-benzoquinone derivatives .
Used in the preparation of bioactive compounds and pharmaceuticals.
Industrial Uses:
Potential applications in wood preservation (as a preservative) and dye intermediates .
Research:
Studied for antioxidant and antiplatelet aggregation properties
FAQ
Q1: What is the primary source and significance of this compound?
A: It is a naturally occurring quinone, often isolated from plants and fungi. Its natural origin makes it a key compound for studying biological interactions and phytochemistry.
Q2: How do the methoxy groups influence its reactivity?
A: The methoxy (-OCH₃) groups are strong electron-donating groups. This makes the quinone core less electron-deficient and therefore a milder electrophile compared to unsubstituted benzoquinone, directing substitution to specific positions and modifying its redox potential.
Q3: What are its main applications in research?
A: Its main applications include:
Organic Synthesis: As a building block for synthesizing more complex molecules, particularly natural product analogs and heterocycles.
Medicinal Chemistry: As a core scaffold for investigating bioactive compounds with antimicrobial, antioxidant, or antitumor properties.
Biological Studies: Used as a substrate or probe in enzymatic studies and to investigate redox processes in biological systems.
Q4: What are the important handling and storage conditions?
A: Store in a cool, dry, and dark place, preferably under an inert atmosphere such as argon or nitrogen to minimize decomposition and oxidation. It should be kept away from strong light and moisture.
Q5: Is this compound considered a PAIN (Pan-Assay Interference Compound)?
A: The quinone structure can be flagged in PAINS filters due to its potential for redox activity and non-specific binding. However, its specific behavior is highly dependent on the assay system. Appropriate control experiments are essential to validate any observed biological activity.
Dibutylbenzoquinone (CAS 3383-21-9) is a stable, sterically hindered ortho-quinone. This compound serves as a key redox-active building block in catalysis, polymer stabilization, and metal coordination chemistry due to its reversible electron transfer capability.
Details
2,6-Di-tert-butylbenzoquinone (CAS 719-22-2) is a sterically hindered quinone derivative, where the bulky tert-butyl groups ortho to the carbonyl functions enhance stability against dimerization and unwanted side reactions.It serves as a versatile oxidizing agent and key intermediate in organic synthesis, particularly in catalytic systems and the preparation of functionalized quinones or ligands.
Details
2,6-Dimethoxybenzoquinone (CAS 530-55-2) is a naturally occurring, methoxy-functionalized quinone derivative commonly found in various plants and fungal species. This compound serves as a versatile building block in organic synthesis, particularly for constructing complex heterocyclic systems and functionalized aromatic structures, leveraging its electron-deficient quinone core as a reactive handle. Its significance extends into biological contexts, where it demonstrates notable bioactive properties, including antimicrobial, antioxidant, and potential antitumor activities, making it a compound of interest in medicinal chemistry and phytochemical research.
Details
2-Chloro-1,4-benzoquinone (CAS 695-99-8) is a highly reactive chlorinated quinone widely used as a key synthetic intermediate in organic chemistry and pharmaceutical research. It serves as a versatile electrophile for nucleophilic substitution reactions and is notably employed in the synthesis of specialized agrochemicals and dyes. This compound requires careful handling due to its toxicity and sensitivity to light and moisture.
Details
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