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.
Name :
DibutylbenzoquinoneCAS No. :
3383-21-9MF :
C₁₄H₂₀O₂MW :
220.31Purity :
99%Appearance :
Dark green to dark brown solidStorage Condition :
Stable under normal conditions but incompatible with reducing agents and strong oxidizersBasic Information
Chemical Name: 3,5-Di-tert-butyl-o-benzoquinone
CAS Number: 3383-21-9
Molecular Formula: C₁₄H₂₀O₂
Molecular Weight: 220.31 g/mol
EINECS Number: 222-189-0
Synonyms:
3,5-Di-tert-butyl-1,2-benzoquinone
DTBQ (common abbreviation)
3,5-Cyclohexadiene-1,2-dione, 3,5-bis(1,1-dimethylethyl)-
Dibutylbenzoquinone
Chemical Properties
Appearance: Dark green to dark brown solid .
Melting Point: 112–114°C (lit.) .
Boiling Point: ~321.25°C (estimated) .
Density: ~1.01 g/cm³ (rough estimate) .
Solubility: Sparingly soluble in chloroform; very slightly soluble in methanol .
Stability: Stable under normal conditions but incompatible with reducing agents and strong oxidizers .
Applications
FAQ
Q1: What are the main hazards and safety precautions for handling this compound?
A: It is an organic solid that may cause irritation to the eyes, skin, and respiratory system. It is advisable to consult its Safety Data Sheet (SDS). Standard laboratory precautions should be used: wear appropriate personal protective equipment (PPE) including gloves and safety glasses, and handle in a well-ventilated area or fume hood. Avoid inhalation of dust and contact with skin.
Q2: How should it be stored?
A: Store in a cool, dry, and well-ventilated place. Keep the container tightly closed and protected from light. It is best stored under an inert atmosphere (e.g., nitrogen or argon) to prevent slow degradation or reduction over long periods.
Q3: Is it naturally occurring?
A: No, 2,5-di-tert-butyl-1,4-benzoquinone is a synthetic compound and is not known to be produced by living organisms.
Q4: What is the difference between this and the common antioxidant BHT (Butylated Hydroxytoluene)?
A: They are structurally related but functionally different. BHT (2,6-di-tert-butyl-4-methylphenol) is a phenolic antioxidant that acts as a radical scavenger. Dibutylbenzoquinone is the oxidized quinone form derived from the oxidation of a related hydroquinone. BHT is an antioxidant, while dibutylbenzoquinone is redox-active and can participate in oxidation-reduction cycles.
Q5: Where can I purchase this compound?
A: It is available from suppliers of fine chemicals, specialty organic compounds, and research chemical distributors (e.g., TCI Chemical, Alfa Aesar, Sigma-Aldrich/Merck). It is typically sold in gram to kilogram quantities for research purposes.
Q6: What is its main use in polymer chemistry?
A: Its primary role is as a mild polymerization inhibitor or modifier. It can terminate growing polymer chains by reacting with radical intermediates, thereby controlling molecular weight or acting as a short-stop agent during certain polymerization processes.
Q7: What is the main application of this compound?
A: It is primarily used as a ligand in coordination chemistry and a redox-active building block in organic synthesis and catalysis. Its sterically hindered structure makes it ideal for stabilizing metal complexes and studying electron transfer processes.
Q8: How does its stability compare to unsubstituted quinones?
A: It exhibits exceptional stability due to steric protection from the two tert-butyl groups, preventing dimerization and decomposition. It can be stored at room temperature, unlike many simpler quinones.
Q9: What purity grades are available?
A: We offer:
Standard Grade: ≥97% (HPLC)
High Purity Grade: ≥99% (HPLC/NMR verified)
All batches include Certificate of Analysis.
Q10: What safety precautions are required?
A: It may cause eye and skin irritation (GHS Category 2). Use standard PPE (gloves, goggles) in a well-ventilated area. It is not classified as a controlled substance.
Q11: Is it soluble in water?
A: No. It is soluble in organic solvents (ethanol, acetone, toluene) but insoluble in water.
Q12: Can you supply custom quantities?
A: Yes. We provide:
R&D samples (1-5g)
Bulk quantities (up to kg scale)
Custom synthesis of analogous compounds
Q13: What's the typical lead time?
A: Small quantities: 1-2 weeks
Bulk/custom orders: 3-5 weeks
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.
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