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 .
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 .
Applications
FAQ
Q1: What are the primary hazards associated with this compound?
A: 2-Chloro-1,4-benzoquinone is toxic, corrosive, and a strong irritant to the skin, eyes, and respiratory system. It is a suspected mutagen and may cause damage to organs through prolonged or repeated exposure. It must be handled with extreme care using appropriate PPE (gloves, goggles, lab coat) in a certified fume hood.
Q2: How should it be stored to maintain stability?
A: Store in a tightly sealed, light-resistant container under an inert atmosphere (e.g., nitrogen or argon) in a freezer (e.g., -20°C). It is sensitive to moisture, heat, and light, and can degrade or polymerize over time. Keep away from strong reducing agents.
Q3: Why is it a significant concern in drinking water?
A: As a representative and relatively stable halogenated benzoquinone disinfection byproduct (DBP), it is orders of magnitude more cytotoxic and genotoxic than regulated DBPs like trihalomethanes. Its presence, even at low concentrations (ng/L), is a marker for the formation of a broader, highly toxic class of unregulated DBPs, driving research for alternative water treatment methods.
Q4: How does its reactivity differ from 1,4-benzoquinone?
A: The chlorine atom makes it a much stronger electrophile than 1,4-benzoquinone. It undergoes nucleophilic substitution reactions more readily. Its redox potential is also altered, and it often exhibits different (and sometimes enhanced) biological activity due to its ability to form stable covalent adducts with biomolecules.
Q5: Where can this chemical be sourced?
A: It is available as a specialty research chemical from suppliers such as Sigma-Aldrich, TCI Chemicals, and Alfa Aesar. It is typically sold in small quantities (milligrams to grams) for laboratory use and is relatively expensive due to its specialized nature and handling requirements.
Q6: What analytical methods are used to detect it?
A: Common methods include Gas Chromatography-Mass Spectrometry (GC-MS) and Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS), often with derivatization (e.g., using dansylhydrazine) to improve sensitivity and stability for trace analysis in complex matrices like water.
Q7: 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
Q8: 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
Q9: 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
Q10: 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)
Q11: 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).
Q12: 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)
Q13: 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
Q14: 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.
Q15: What documentation is provided?
A:
Safety Data Sheet (GHS compliant)
Stability data and storage recommendations
Reaction protocol examples
Waste disposal guidelines
Q16: 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.
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