1,4-Dichlorobenzene - ≥99%, used for Used as an insecticide fumigant, moth repellent, deodorant, preservative, analytical reagent and for organic synthesis. various applications , CAS No.106-46-7

CAS: 106-46-7 Cat. No.: D104676 Formula: C₆H₄Cl₂ Molecular Weight: 147 Beilstein Registry Number: 1680023 EC Number: 203-400-5

GRADE & PURITY ≥99%

Synonyms

paradichlorobenzene | para-Dichlorobenzene | 1,4-Diclorobenzene(ITALIAN) | Paracide | HY-Y0496 | PARADICHLOROBENZENE [WHO-DD] | p-Dichloorbenzeen | p-Diclorobenzene(ITALIAN) | 1,4-chlorobenzene | UNII-D149TYB5MK | CHEBI:28618 | Evola | RCRA waste number U

Storage

Protected from light,Room temperature,Desiccated

Shipped In

Normal

Specifications

Synonyms

paradichlorobenzene | para-Dichlorobenzene | 1,4-Diclorobenzene(ITALIAN) | Paracide | HY-Y0496 | PARADICHLOROBENZENE [WHO-DD] | p-Dichloorbenzeen | p-Diclorobenzene(ITALIAN) | 1,4-chlorobenzene | UNII-D149TYB5MK | CHEBI:28618 | Evola | RCRA waste number U

Specifications & Purity

≥99%

Application

Used as an insecticide fumigant, moth repellent, deodorant, preservative, analytical reagent and for organic synthesis.

Storage

Protected from light,Room temperature,Desiccated

Shipped In

Normal

Purity

≥99%

Names and Identifiers

Pubchem Sid

504750798

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504750798

Canonical Smiles

C1=CC(=CC=C1Cl)Cl

IUPAC Name

1,4-dichlorobenzene

InChIKey

OCJBOOLMMGQPQU-UHFFFAOYSA-N

INCHI

1S/C6H4Cl2/c7-5-1-2-6(8)4-3-5/h1-4H

Isomeric SMILES

C1=CC(=CC=C1Cl)Cl

WGK Germany

1

UN Number

3077

Packing Group

III

Molecular Weight

147

Beilstein

1680023

Reaxy-Rn

1680023

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1680023&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Halobenzenes
        • Level5 Chlorobenzenes
          • Level6 Dichlorobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Chlorobenzenes
• Direct Parent: Dichlorobenzenes
• Alternative Parents: Aryl chlorides Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 1,4-dichlorobenzene - Aryl halide - Aryl chloride - Hydrocarbon derivative - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
• External Descriptors: a chloroaromatic compound

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MAOA Tclin Monoamine oxidase A (11911 Activities)

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CASP3 Tchem Caspase-3 (3632 Activities)

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CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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Associated Targets(non-human)

Cyp2a5 Cytochrome P450 2A5 (126 Activities)

Discover Target: Cyp2a5

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Caenorhabditis elegans (1055 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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ced-3 Cell death protein 3 (4 Activities)

Discover Target: ced-3

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Insoluble in water, soluble in ethanol, ether, and benzene.
• Sensitivity: light sensitive
• Flash Point(°C): 65.56°C
• Boil Point(°C): 174.12°C
• Melt Point(°C): 53.5°C
• Molecular Weight: 147.000 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 145.969 Da
• Monoisotopic Mass: 145.969 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 54.900
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable for this chemical building block. No validated immunoassay or cell-based application protocols are provided for this item.

• General usage examples (literature)
  • For cross-coupling reactions, follow standard Pd-catalyzed coupling protocols as outlined under Reaction Conditions, adapting catalyst/ligand/base to your substrate scope.
  • For purification, recrystallization from ethanol/toluene or sublimation under reduced pressure can be effective (procedure optimization recommended).

Biological Roles

This section summarizes literature knowledge; no biological specifications are provided for this particular item.

• Biological and environmental fate (literature)

  • p-Dichlorobenzene is a hydrophobic, volatile organic compound. In biota and environmental systems, it partitions to lipophilic phases; biodegradation is slow but can occur via oxidative dechlorination pathways in specialized microbes.
  • Metabolism in mammals generally involves cytochrome P450-mediated oxidation to chlorophenols and ring-hydroxylated metabolites, followed by conjugation (e.g., glucuronides/sulfates) and excretion.

• Biochemical interactions (general)

  • Nonpolar aromatic compounds can interact with biological membranes; specific receptor-level interactions are not a primary mode of action for this small molecule.

• Toxicological context (literature; not item-specific and not a medical claim)

  • Reported to display narcotic-like effects at high vapor concentrations (general hydrocarbon effect). Possible carcinogenicity has been evaluated (IARC Group 2B) in the literature.

Note: This product is supplied strictly for research use (per Product Data). No clinical, diagnostic, or in vivo use is implied.

Buffer Applications

1,4-Dichlorobenzene is a nonpolar, water-insoluble aromatic solid and is not used to prepare aqueous buffers or to control pH.

• Practical guidance
  • If introduced into aqueous systems (e.g., partitioning studies), use cosolvents or emulsifiers and maintain separate buffer preparation using standard buffering agents (phosphate, Tris, acetate).

Green Alternatives

Considerations relate to choosing greener reagents, catalysts, and solvents when using 1,4-dichlorobenzene (p-DCB) as an aryl electrophile.

• Greener process choices (literature guidance)

  • Solvents: Replace chlorinated solvents (DCM, chloroform) and dipolar aprotics (DMF, NMP) with 2-MeTHF, CPME, propylene carbonate, or bio-derived esters where compatible with the catalyst system.
  • Catalysts/ligands: Employ ligand systems that enable lower catalyst loadings and milder temperatures for aryl chloride activation (e.g., BrettPhos, tBuBrettPhos, SIPr–Pd for PEPPSI). Lower energy input reduces footprint.
  • Bases: Favor inorganic bases with lower hazard profiles (K3PO4, K2CO3) over strong alkoxides when feasible.

• Comparison snapshot (general)

| Option | Benefit | Trade-offs | |---|---|---| | 2-MeTHF vs THF | Bio-based, higher bp allows lower solvent loss | Can affect catalyst solubility/turnover | | CPME vs toluene | Hydrophobic, forms low peroxides, recyclable | Slightly higher cost; different azeotrope behavior | | Aryl boronic esters vs organostannanes | Lower toxicity, easier workup | Sensitive to base/protodeboronation |

• Environmental notes
  • p-DCB is volatile and persistent; minimize emissions by using closed systems and condensers; capture vapors with activated carbon.
  • Choose energy-efficient heating (e.g., flow or microwave with validated safety) to shorten reaction times.

These are general, literature-based recommendations to improve process sustainability while using 1,4-dichlorobenzene.

Pharmaceutical Uses

No pharmacopeial/excipient status or formulation role is specified for this item.

• General (literature; not item-specific)

  • 1,4-Dichlorobenzene is occasionally encountered as a synthetic intermediate toward para-disubstituted benzene scaffolds but is not used as an excipient. Due to toxicity and environmental concerns, its presence in pharmaceutical manufacturing is typically limited to intermediate or impurity contexts, subject to stringent control and purge strategies.

• Process considerations

  • When used upstream in API or intermediate synthesis, incorporate appropriate purge evaluations and residual solvent/impurity testing (e.g., GC) to meet regulatory expectations.

No therapeutic or clinical claims are made. For research and process development use only (per Product Data).

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/typical values (not item-specific; for reference only)

  • Physical state: crystalline solid (often white needles or flakes)
  • Melting point: ~53–54 °C (literature)
  • Boiling point: ~173–175 °C at 1 atm (literature)
  • Density (solid): ~1.46 g/cm³ at 20–25 °C (literature)
  • Vapor pressure: ~0.6–0.8 mmHg at 25 °C (literature)
  • Water solubility: very low, ~70–90 mg/L at 25 °C; increases slightly with temperature (literature)
  • Organic solubility: miscible with nonpolar/aprotic media (e.g., benzene, toluene, chloroform, dichloromethane); good solubility in ethers and acetone (literature)
  • Log Kow (octanol/water): ~3.3–3.6 (literature)
  • Henry’s law constant: ~2×10⁻³ to 5×10⁻³ atm·m³/mol (literature)
  • Refractive index: typically reported for molten/liquid near the mp; values ~1.56–1.58 (literature)
  • UV characteristics: strong absorption <250 nm; weak tail into near-UV typical of chlorinated benzenes (literature)

• Interpretive notes (general)

  • Low polarity and low aqueous solubility enable liquid–liquid extraction into nonpolar solvents.
  • Sublimation can occur near room temperature under reduced pressure; handle in well-ventilated areas to minimize inhalation of sublimate.

All numerical values above are literature guidance only and are not item specifications.

Quality & Grades

• Item-specific details (from Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades for 1,4-dichlorobenzene (general guidance)

  • Analytical Reagent (AR) or ACS grade: Tight impurity control suitable for quantitative analysis; lower nonvolatile residue; trace-metals screened.
  • GC/Chromatography grade: Low background in GC/LC; minimized UV-absorbing impurities; suitable as a reference standard or matrix component in method development.
  • Technical grade: Adequate for bulk transformations where trace impurities are tolerated; not intended for analytical use.

• Stabilizers and additives

  • 1,4-Dichlorobenzene is typically shipped unstabilized. If a stabilizer were included, it would be disclosed on the CoA/SDS. None are specified for this item.

• Practical quality notes (general)

  • Common impurities: Other dichlorobenzene isomers (o-/m-), monochlorobenzene, chlorinated byproducts, residual solvents. For cross-coupling chemistry, these can influence reactivity and GC/MS profiles.
  • Verification: Confirm identity by mp (~53–54 °C), GC purity, and 1H/13C NMR (singlet pattern consistent with para symmetry: two aromatic signals in 1H NMR, two in 13C NMR).

Always consult the item’s CoA/Spec Sheet for authoritative specifications and impurity profiles.

Reaction & Applications

• General reactivity overview (literature)

  • Aryl chloride electrophile; two equivalent C–Cl bonds enable mono- or bis-functionalization to access para-disubstituted benzenes.
  • Direct SNAr is challenging due to the lack of ring-activating substituents; requires harsh conditions or specific nucleophiles. Modern Pd/Ni catalysis overcomes this limitation.

• Named reaction families (typical for aryl chlorides)

  • Suzuki–Miyaura coupling: Formation of biaryls from boronic acids/esters using Pd catalysts with tailored ligands (e.g., SPhos, XPhos, BrettPhos) to activate aryl chlorides.
  • Buchwald–Hartwig amination: C–N bond formation to anilines using strong bases and bulky electron-rich phosphines.
  • Kumada, Negishi, Stille: C–C bond formation with Grignard, organozinc, or organostannanes; Ni or Pd catalysis.
  • Ullmann-type couplings (Cu or Pd) under more forcing conditions.

• Representative applications (examples; literature)

  • Divergent synthesis: Stepwise, selective mono-coupling followed by a second orthogonal coupling to install two distinct para substituents (e.g., Ar1–C6H4–Ar2).
  • Halogen–lithium exchange on aryl chlorides is generally impractical; instead, metal–halogen exchange is done on bromides/iodides. For p-DCB, directed metalation is not favored; cross-coupling is preferred.
  • Material science: Precursor to para-disubstituted polyaromatics and liquid-crystalline cores.

• Practical notes (general)

  • Ensure anhydrous, oxygen-limited conditions for cross-coupling. Choose strong bases (K3PO4, Cs2CO3, tBuONa) and high temperatures (80–120 °C) as needed for aryl chloride activation.
  • Use a high-boiling solvent (toluene/xylene/chlorobenzene/1,4-dioxane) and robust catalysts (Pd-PEPPSI, Pd2(dba)3/XPhos).

No manufacturer-specific applications are provided in the Product Data.

Reaction Conditions

The following are literature-derived, non-item-specific examples for aryl chloride activation in 1,4-dichlorobenzene. Optimize per substrate and scale.

• Suzuki–Miyaura biaryl coupling (aryl chloride)

  • Catalyst: Pd2(dba)3 (1–2 mol% Pd) + XPhos/SPhos (2–4 mol%) or a precatalyst (e.g., Pd-PEPPSI-IPr 1 mol%).
  • Base: K3PO4 (2–3 equiv) or Cs2CO3 (2–3 equiv).
  • Solvent: Toluene, 1,4-dioxane, or mixed toluene/H2O; concentration 0.1–0.5 M.
  • Temperature/time: 90–120 °C, 4–16 h. Typical isolated yields for mono-coupling 60–90% with optimized systems; bis-coupling may require higher catalyst loadings.

• Buchwald–Hartwig amination

  • Catalyst/ligand: Pd2(dba)3 (1–2 mol% Pd) + BrettPhos/tBuBrettPhos (2–4 mol%); or Pd-precatalysts (e.g., XPhos Pd G2).
  • Base: NaOtBu or Cs2CO3 (2–3 equiv).
  • Solvent: Toluene, tAmOH, or dioxane.
  • Temperature: 90–110 °C; 6–18 h. Anilines typically obtained in good yields under optimized conditions.

• Sonogashira coupling (to aryl alkynes)

  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%).
  • Base: Et3N or iPr2NH.
  • Solvent: Toluene/Et3N or DMF.
  • Temperature: 60–90 °C; 6–16 h. For aryl chlorides, more active ligands or higher temperature may be required.

• Notes

  • Use rigorously anhydrous conditions and degassed solvents. Aryl chloride activation is ligand-sensitive; screen ligands and bases early.
  • For bis-functionalization, perform sequential couplings with careful control of conversion to avoid over- or under-substitution.

Safety & Handling

• Item-specific safety fields (from Product Data)

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety information (literature; not item-specific — always defer to the SDS for authoritative guidance)

  • Hazard profile: Chlorinated aromatic hydrocarbon; harmful if swallowed or inhaled; may cause skin/eye irritation; environmentally hazardous to aquatic life; possible carcinogenicity has been discussed in the literature (IARC 2B for p-dichlorobenzene).
  • Special risks: Volatile/sublimes; vapors heavier than air; combustible solid. Avoid dust generation and heating in confined spaces.
  • Peroxide formation: Not a peroxidizable solvent (unlike ethers), but can slowly chlorinate/oxidize under harsh conditions; avoid strong oxidizers.
  • Incompatibilities: Strong oxidizing agents, strong bases at elevated temperature (can promote substitution/elimination), nitrating mixtures.

• Handling & PPE (general best practice)

  • Work in a fume hood; avoid inhalation of vapor/sublimate.
  • Wear safety glasses or goggles, lab coat, and suitable chemical-resistant gloves (e.g., nitrile). For bulk handling, consider a dust mask/respirator per risk assessment.
  • Prevent release to the environment; collect waste in halogenated-organic streams.

• First aid (overview — consult SDS)

  • Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms persist.
  • Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; get medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Fire-fighting (general)

  • Use dry chemical, CO2, or foam; water spray to cool containers. Combustion may produce HCl and phosgene; firefighters should wear SCBA.

Solvent Selection

This product is a solid aromatic building block, not a solvent. Solvent selection therefore refers to choosing appropriate media to dissolve or react 1,4-dichlorobenzene.

• Solubility-driven choices (literature)

  • Highly soluble in nonpolar and moderately polar aprotic solvents: toluene, xylene, chlorobenzene, DCM, chloroform, THF, 1,4-dioxane, acetone.
  • Very low solubility in water; aqueous systems are generally unsuitable without a cosolvent or surfactant.

• Polarity and dielectric considerations (general)

  • As a nonpolar aromatic, p-DCB dissolves best in solvents with aromatic character (toluene, chlorobenzene) via π–π and dispersion interactions.

• Practical guidance (general)

  • For Pd-catalyzed cross-couplings of aryl chlorides, high-boiling aromatic solvents (toluene, xylene, chlorobenzene) or polar aprotics (DMF, NMP, dioxane) are commonly used.
  • For recrystallization, ethanol or methanol mixed with a nonpolar solvent can effect purification by differential solubility; toluene/ethanol systems are common.

Note: No item-specific solvent data are provided; select media based on reaction requirements and literature precedent.

Storage & Reconstitution

• Item-specific storage (from Product Data)

  • Storage Conditions: Protected from light; Room temperature; Desiccated; Cool.
  • Shipped In: Normal.

• Practical guidance (general)

  • Keep tightly closed in a dry, well-ventilated place. Store in an amber container or within secondary light protection to minimize photolytic degradation and volatilization.
  • Minimize headspace to limit sublimation/volatilization; consider cold-room storage for long-term retention, consistent with “Cool” and room-temperature allowance in Product Data.
  • Use desiccant to maintain dryness; moisture is not a primary degradation pathway but dryness benefits many coupling reactions.

• Reconstitution

  • Not applicable: product is a solid organic compound, typically weighed directly. If a solution stock is desired, dissolve in a suitable anhydrous organic solvent (e.g., toluene, THF, DCM) at the required concentration and store in sealed, light-protected vials at controlled temperature. Validate solution stability by GC before extended storage.

Always follow your institution’s SDS and safety protocols when handling and storing this material.

Structure & Identity

Brief description: 1,4-Dichlorobenzene (p-DCB) is a symmetric para-disubstituted chlorinated benzene; two chlorine atoms occupy para positions on a benzene ring.

• Item-specific (from Product Data)

  • SKU: D104676
  • Product Name: 1,4-Dichlorobenzene
  • CAS: 106-46-7
  • PubChem CID: 4685
  • InChIKey: 254183
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (non-item-specific)

  • Common synonyms: p-Dichlorobenzene; p-DCB; 1,4-DCB
  • Molecular formula (literature): C6H4Cl2
  • Exact mass (calculated): 146.969 g/mol; average MW ~147.00 g/mol (literature)
  • SMILES (literature): Clc1ccc(cc1)Cl
  • InChIKey (literature): YMWUJEATGCHHMB-UHFFFAOYSA-N

• Structural features (general)

  • Aromatic ring: planar benzene with delocalized π-system
  • Substitution pattern: para-1,4-dichloro; C2v symmetry; two equivalent C–Cl aryl bonds
  • Functional groups: two aryl chlorides (deactivated toward SNAr; suitable for Pd-catalyzed cross-coupling with appropriate ligands)
  • 2D description: a six-membered aromatic ring with chlorine atoms at positions 1 and 4; remaining positions 2,3,5,6 are unsubstituted hydrogens; no stereocenters or E/Z isomerism due to ring substitution

Notes: Item-specific identifiers above reflect the provided Product Data; literature identifiers are supplied for context only.

Synthetic Utility

• Symmetry-enabled diversification

  • Two equivalent aryl chloride sites enable stepwise or tandem bis-functionalization, affording para-disubstituted products with high regiochemical control.

• Key transformations (literature)

  • Pd-catalyzed cross-couplings at aryl chlorides using electron-rich, bulky phosphines or NHC ligands: Suzuki–Miyaura (to biaryls), Buchwald–Hartwig (to anilines), Sonogashira (to aryl alkynes), and Negishi/Kumada/Stille (to diverse C–C bonds).
  • Radical or photoredox strategies can activate aryl chlorides under milder conditions (e.g., dual Ni/photoredox for C–N or C–C couplings), though optimization is substrate- and ligand-dependent.

• Retrosynthetic value

  • p-DCB serves as a convergent hub for building symmetric or unsymmetric para-disubstituted benzenes: Ar1–C6H4–Ar2, R–C6H4–X, etc. Choice of sequence (which C–Cl reacts first) can be tuned via steric/electronic effects and catalyst/ligand selection.

• Practical points

  • Aryl chlorides are less reactive than bromides/iodides; compensate via higher temperature, optimized ligands, or switching to aryl bromide analogs if necessary.
  • Monitor for isomeric impurities (o-/m-DCB) that can complicate chromatographic separation; verify with GC and 2D NMR if needed.

Target Specificity

Not applicable. This product is a small-molecule chemical, not a biological affinity reagent (e.g., antibody, enzyme inhibitor with defined biological target for this listing). No target, clone, isotype, or species reactivity information is relevant.