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.
Name :
2-Chloro-1,4-benzoquinoneCAS No. :
695-99-8MF :
C₆H₃ClO₂MW :
142.54Purity :
99%Appearance :
Yellow to brown crystalline solidStorage Condition :
Stable under normal conditions but decomposes when heated, releasing toxic gasesBasic Information
Chemical Name: 2-Chloro-1,4-benzoquinone
CAS Number: 695-99-8
Molecular Formula: C₆H₃ClO₂
Molecular Weight: 142.54 g/mol
EINECS Number: 211-761-3
Synonyms:
Chloroquinone
Monochloroquinone
2-Chloro-p-benzoquinone
Benzoquinone, 2-chloro-
Physical and Chemical Properties
Appearance: Yellow to brown crystalline solid .
Melting Point: 52–57°C .
Boiling Point: ~210°C (decomposition) .
Density: 1.40 g/cm³ .
Solubility:
Slightly soluble in water.
Soluble in organic solvents (e.g., ethanol, ether) .
Flash Point: 83°C .
Stability: Stable under normal conditions but decomposes when heated, releasing toxic gases .
Key Applications
Organic Synthesis:
Acts as an oxidizing agent in reactions involving alcohols, ethers, amines, and thiols .
Used in the degradation of 3,4-dichloroaniline via dielectric barrier discharge plasma .
Industrial Uses:
Fungicide and wood preservative .
Intermediate in pharmaceutical and agrochemical synthesis .
Research:
Studied for its role in lignin peroxidase-catalyzed oxidation of 2-chloro-1,4-dimethoxybenzene .
Safety and Handling
Hazard Classification:
Risk Statements:
R36/37/38: Irritating to eyes, respiratory system, and skin .
R10: Flammable .
Precautionary Measures:
Wear PPE (gloves, goggles, protective clothing).
Use in well-ventilated areas; avoid inhalation or contact with skin/eyes .
Regulatory Status:
Classified under HS Code 2914.70.00 (chlorinated quinones) .
Synthesis Methods
Primary Routes:
Oxidation of 2-Chloroaniline Derivatives: Reacts with strong oxidizing agents (e.g., DDQ) to form the quinone structure .
Electrochemical Synthesis: Generated via electrolysis of chlorinated benzene derivatives .
Purification: Recrystallization from ethanol or sublimation under vacuum .
FAQ
Q1: What is the primary application of this compound?
A: It serves as a versatile electrophilic synthon in organic synthesis, particularly for:
Peptide coupling agents in bioconjugation
Polymerization inhibitor in acrylic monomers
Intermediate for dyes and agrochemicals
Q2: What safety precautions are critical?
A: This compound is highly reactive and toxic:
GHS Classification: Acute Tox. 3, Skin Corr. 1B, Aquatic Acute 1
Mandatory PPE: Acid-resistant gloves, vapor goggles, fume hood
Storage: Store under inert gas at -20°C in sealed amber vials
Q3: How is purity verified?
A: We provide:
HPLC/GC purity (≥97% standard, ≥99% available)
NMR for structural confirmation
Chlorine content assay via ion chromatography
All batches include full Certificate of Analysis
Q4: Why does it require cold storage?
A: It polymerizes exothermically above 10°C and decomposes upon prolonged light exposure. Cold storage prevents:
Loss of reactivity
Formation of hazardous decomposition products
Color degradation (indicator of stability)
Q5: Can it be used in aqueous systems?
A: Not recommended – hydrolyzes rapidly in water (t½ <30 min). Use under strictly anhydrous conditions in aprotic solvents (ACN, THF, DCM).
Q6: What’s the lead time for orders?
A:
Research samples (1-5g): 1-2 weeks (often in stock)
Bulk quantities (>100g): 4-6 weeks (synthesized on demand)
Q7: Do you offer stabilized formulations?
A: Yes. Available as:
10% w/w solid dispersion in KBr (for safer handling)
0.1M solution in dry acetonitrile (ready for reactions)
Custom concentrations available
Q8: Is it compatible with common reagents?
A: Reacts violently with:
Nucleophiles (amines, thiols)
Reducing agents (NaBH₄, Zn)
Strong bases
Test compatibility on small scale first.
Q9: What documentation is provided?
A:
Safety Data Sheet (GHS compliant)
Stability data and storage recommendations
Reaction protocol examples
Waste disposal guidelines
Q10: Can it be used in bioconjugation?
A: Yes – it selectively reacts with:
Cysteine thiols (pH 7-8)
Histidine imidazole groups
Unprotected N-termini
Requires precise stoichiometry control.
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
