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.
Name :
2,6-Di-tert-butylbenzoquinoneCAS No. :
719-22-2MF :
C₁₄H₂₀O₂MW :
220.31Purity :
99%Appearance :
Orange to brown crystals or crystalline powderStorage Condition :
Light-sensitive; requires storage under inert atmosphere at -20°CBasic Information
Chemical Name: 2,6-Di-tert-butylbenzoquinone
CAS Number: 719-22-2
Molecular Formula: C₁₄H₂₀O₂
Molecular Weight: 220.31 g/mol
EINECS Number: 211-946-0
Synonyms:
2,6-Di-tert-butyl-p-benzoquinone
BHT-quinone
3,5-Di-tert-butyl-1,4-benzoquinone
2,6-Di-tert-butylcyclohexa-2,5-diene-1,4-dione
Physical and Chemical Properties
Appearance: Orange to brown crystals or crystalline powder .
Melting Point: 65–67°C (lit.) .
Boiling Point: 75–80°C (0.7 mmHg) .
Density: ~1.01 g/cm³ (estimated) .
Solubility:
Slightly soluble in chloroform and methanol .
Insoluble in water .
Stability: Light-sensitive; requires storage under inert atmosphere at -20°C .
Key Applications
Organic Synthesis:
Acts as an oxidizing agent in Diels-Alder reactions and oxidative dehydrogenation .
Used in the synthesis of benzoxazole derivatives and heterocyclic compounds .
Pharmaceuticals:
Investigated as a precursor for antitumor agents and antimicrobial compounds .
Industrial Uses:
Functions as a ligand in coordination chemistry for metal complexation .
Applied in UV-stable polymers and organic electronic materials .
Safety and Handling
Hazard Classification:
Risk Statements: H315 (skin irritation), H319 (serious eye damage), H335 (respiratory irritation) .
Precautionary Measures:
Use P261 (avoid inhalation), P280 (wear protective gloves/eye protection) .
Store in a sealed, dry environment away from strong oxidizers .
Synthesis Methods
Primary Routes:
Oxidation of 2,6-Di-tert-butylphenol: Reacts with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) under controlled conditions .
Cyclization Reactions: Involving substituted cyclohexadienones .
Purification: Recrystallization from methanol or sublimation under vacuum
FAQ
Q1: What is the key functional feature of this quinone?
A: Its key feature is steric hindrance. The bulky tert-butyl groups adjacent to the carbonyls prevent dimerization and unwanted side reactions, making it a more stable and predictable reagent than unsubstituted benzoquinones.
Q2: What is its primary application in synthesis?
A: It is primarily used as a mild oxidizing agent. It is particularly effective in catalytic cycles, such as oxidizing palladium(0) to palladium(II) in aerobic oxidation reactions, and in the synthesis of other sterically hindered compounds.
Q3: How does the steric hindrance benefit its use?
A: The hindrance provides enhanced stability (resistance to decomposition), selectivity in reactions by blocking certain sites, and solubility in common organic solvents.
Q4: What are the important handling and storage considerations?
A: Store in a cool, dry place protected from light and moisture. While more stable than other quinones, long-term integrity is best maintained under an inert atmosphere (e.g., N₂).
Q5: Is this compound suitable for developing antioxidant materials?
A: Ironically, yes. Its quinone structure allows it to participate in redox cycles, making it a useful building block for creating polymer stabilizers and antioxidants, where it acts as a radical scavenger.
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
Contact Us
1st Floor, No. 477, Huancheng West Road, Nanqiao Town, Fengxian District, Shanghai,China
sales@qxscientific.com
+86 -13701740203
IPv6 Network Supported |
Sitemap |
XML |
Blog |
Privacy Policy
Leave A Message
Scan to Wechat/Whatsapp :
English
English
Español
Português
