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
Not available
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.
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Application Protocols
Not applicable for assay protocols such as WB, IHC, IF, or FC. This item is a chemical intermediate used in organic synthesis. For practical use, consult the Reaction Conditions section for representative coupling/derivatization procedures, and confirm exact stoichiometry and conditions with current literature and your internal SOPs.
Biological Roles
Item is a small halogenated aromatic used as a synthetic intermediate. No physiological “role” is expected.
General information (literature):
Xenobiotic profile: Polyhalogenated benzenes are not endogenous metabolites. If introduced to biological systems, they are typically metabolized slowly, involving oxidative pathways (e.g., cytochrome P450-mediated aromatic hydroxylation) followed by conjugation (glucuronidation/sulfation). Dehalogenation can occur but is substrate- and enzyme-dependent.
Physicochemical properties (logP ~3–3.5, low aqueous solubility) suggest membrane partitioning and potential bioaccumulation concerns typical of halogenated aromatics; hence appropriate environmental controls are advised in research settings.
Bioreactivity: Without strong electron-withdrawing groups, the aryl C–Cl and C–F bonds are relatively inert in aqueous biochemical contexts. Reactivity is generally observed only under engineered catalytic/chemical conditions.
Use context: This compound is intended for laboratory synthesis of more complex molecules that may be screened in biochemical assays. Any biological data would pertain to downstream derivatives rather than the starting material itself.
Compliance note: For research use only; not intended for diagnostic, therapeutic, or other clinical applications.
Buffer Applications
Not typically applicable. 2,5-Dichlorofluorobenzene is a nonionic, water-insoluble aromatic and does not participate in acid/base equilibria relevant to buffering.
Practical note: When used in aqueous-organic systems (e.g., Suzuki couplings), buffers or bases (K3PO4, Cs2CO3) may be present to support catalysis, but the compound itself is not a buffer component.
Green Alternatives
Because this product is a substrate rather than a process solvent, “green alternatives” relate to how you use it:
Greener coupling media (literature):
Prefer 2-MeTHF, CPME, or toluene over dioxane/DMF when compatible. These reduce peroxide risk (vs ethers like THF) and improve EHS/egress characteristics.
Use aqueous micellar catalysis (e.g., TPGS-750-M) for Suzuki couplings under mild conditions to minimize organic solvent usage.
Chloride vs bromide/iodide electrophiles (literature comparison):
Using aryl chlorides (this item) avoids reliance on scarcer, higher-toxicity bromides/iodides and often lowers cost and halogenated waste burden, at the expense of higher activation energy (requiring optimized ligands and higher temperatures).
Energy and waste reduction (literature):
Employ highly active Pd precatalysts (Buchwald-type, PEPPSI) to reduce catalyst loading and temperature.
Telescoping sequences (e.g., in situ boronation then coupling) can minimize isolations and solvent swaps.
Note: If your route allows, consider introducing fluorine later via electrophilic fluorination or deoxyfluorination on a partially built scaffold to reduce handling of polyhalogenated starting materials; trade-off is step count/chemoselectivity.
Pharmaceutical Uses
No excipient or compendial role is expected for this material. It is best viewed as a research intermediate/building block in synthetic routes.
Process chemistry context (literature):
Role: Halogenated aryl electrophile for constructing substituted phenyl motifs via cross-coupling or nucleophilic substitution (rare) en route to candidate APIs, agrochemicals, or materials.
Advantages: Orthogonal C–Cl and C–F bonds allow stepwise diversification and late-stage modifications while maintaining a fluoro handle for electronic tuning.
Considerations: Residual aryl halides can be genotoxic impurities in drug substances. If used in GMP settings, rigorous purge studies and appropriate analytical controls (GC/HPLC with selective detectors or HRMS) are required. Any pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet.
Regulatory note: For research use only. Not for human or veterinary use. No therapeutic claims are made or implied.
Physical Properties
Note: Specific item-level specifications (e.g., density, UV cutoff) are not provided for this SKU. Values below are typical literature data for 2,5-dichlorofluorobenzene and are offered for general guidance only—verify with CoA/Spec Sheet and SDS before use.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Phase at RT: typically a colorless to pale yellow liquid (literature, halogenated benzenes of this MW)
Acidity/basicity: no titratable functional group; not a buffer component (literature)
Item-specific numerical specifications (water/peroxides/UV cutoff/trace metals): Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
For halogenated aryl building blocks used in cross-coupling, impurities such as hydrodehalogenated benzenes, isomeric halides, or residual halogenated solvents can impact reactivity and selectivity. Review the CoA for assay (GC) and key impurity profiles when optimizing metal-catalyzed couplings.
Low water content is usually beneficial for moisture-sensitive transformations (e.g., metal–halogen exchange, Grignard formation). If water specification is critical to your application, confirm on the CoA or request Karl Fischer data. Item-specific water content: Not specified for this item; refer to CoA/Spec Sheet.
For use in photoredox or high-sensitivity applications, UV absorbance and metal trace limits may matter. UV cutoff and trace metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Batch-to-batch consistency: Check retention time by GC and identity by MS/NMR on receipt when stringent reproducibility is required (e.g., multistep route intermediates). Retain a sample of each lot for route requalification.
Reaction and Applications
As a tri-halogenated arene, 2,5-dichlorofluorobenzene provides orthogonal C–X bonds enabling stepwise functionalization. Typical research applications (literature) include:
Selective cross-coupling at C–Cl positions (literature):
Pd-catalyzed Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira, and Negishi couplings can target aryl chlorides using modern ligand sets (e.g., SPhos, XPhos, BrettPhos, RuPhos). The aryl C–F bond commonly remains intact under these conditions, serving as a latent handle for later transformations or as an electronic modulator.
SNAr considerations (literature):
Aryl fluorides are typically the preferred leaving group in SNAr, but activation requires strong ring electron withdrawal (–NO2, –CN). With only halogens present, SNAr is generally unproductive; cross-coupling strategies are preferred.
Orthogonal derivatization (literature):
Regiodivergent sequences: first functionalize one C–Cl (e.g., amination), then address the second C–Cl or, with specialized catalysts, attempt C–F activation.
Metal–halogen exchange (literature):
Halogen–magnesium exchange on aryl chlorides is feasible with i-PrMgCl·LiCl (Turbo Grignard) in THF at low temperature, enabling subsequent trapping with electrophiles. Halogen–lithium exchange is far less favorable on C–Cl/C–F and generally requires harsh conditions; proceed with caution.
Applications in discovery and materials (literature):
Intermediate for agrochemical and specialty monomer synthesis, fluorinated arene scaffolds for OLED/OPV materials, and SAR exploration in medicinal chemistry programs (as a building block—no clinical claims).
Tip: Exploit differential reactivity of the two C–Cl sites by ligand/catalyst choice and sterics; 2-position (ortho to F) may display subtly different rates than 5-position depending on conditions.
Reaction Conditions
General literature guidance for transformations of aryl chlorides in this scaffold (optimize per substrate and scale):
Suzuki–Miyaura coupling (Ar–Cl to Ar–C(sp2))
Catalyst/ligand: Pd2(dba)3 (0.5–1 mol% Pd) with SPhos/XPhos (1–2 mol%); or precatalysts like Pd-PEPPSI-IPr (0.5–1 mol%).
Base: K3PO4 (2–3 equiv) or Cs2CO3; aqueous base often beneficial.
Solvent: 1,4-dioxane/H2O (3:1) or toluene/H2O; 80–110 °C; 2–12 h.
Notes: The C–F bond typically survives. Sterics can differentiate 2- vs 5-chloro positions.
Buchwald–Hartwig amination (Ar–Cl to Ar–NR2)
Catalyst/ligand: Pd(OAc)2 (1–2 mol%) with BrettPhos or RuPhos; or XPhos-based precatalysts.
Base: NaOtBu or Cs2CO3 (2–3 equiv).
Solvent: toluene or dioxane; 90–120 °C; 4–16 h.
Notes: Bulky ligands improve oxidative addition to Ar–Cl.
Sonogashira coupling (Ar–Cl to Ar–C≡CR)
Catalyst: PdCl2(PPh3)2 (1–2 mol%) + CuI (2–5 mol%); or copper-free with Buchwald ligands.
Base: i-Pr2NH/Et3N; Solvent: toluene/THF; 60–100 °C.
Halogen–magnesium exchange (Turbo Grignard)
Reagents: i-PrMgCl·LiCl (2–3 equiv) in THF.
Conditions: −78 to 0 °C, 0.5–2 h, then electrophile quench (e.g., DMF for formylation).
Notes: Strictly anhydrous; validate feasibility on this substrate due to lower exchange rates of Ar–Cl.
C–F activation (advanced)
Nickel or photoredox/nickel dual catalysis for borylation or defluorinative coupling; often requires specialized ligands, high temperatures, or light-driven setups.
These are representative literature conditions; tailor to your setup. Always conduct small-scale feasibility before scale-up.
Safety and Handling
Item-specific hazard statements, pictograms, and GHS classification: Not specified for this item; refer to the product SDS for authoritative information.
General safety guidance for halogenated aromatics (literature/typical):
Hazards: May cause skin/eye irritation and respiratory irritation. Many halogenated aromatics are harmful if swallowed or inhaled and may be hazardous to aquatic environments. Combustible but generally higher flash points than light solvents.
PPE: Use chemical-resistant gloves (e.g., nitrile), safety goggles/face shield, lab coat. Work in a fume hood to avoid inhalation.
Handling: Avoid breathing vapors or mist. Prevent release to the environment. Use only with adequate ventilation. Keep away from strong bases and strong nucleophiles that could lead to undesired reactions; avoid strong oxidizers and reducing agents.
Storage: As per Product Data, store at room temperature. Keep container tightly closed, in a cool, well-ventilated area, away from heat/sparks/open flames. Protect from moisture ingress; store segregated from oxidizers.
First aid (overview; defer to SDS): If inhaled, move to fresh air. In case of skin contact, wash with soap and water. For eye contact, rinse cautiously with water for several minutes and seek medical attention. If swallowed, rinse mouth; seek medical advice—do not induce vomiting unless directed by medical personnel.
Spill/Fire: For small spills, absorb with inert material and dispose per regulations. For fire, use dry chemical, CO2, or foam; avoid water jets on organic liquid fires.
Solvent Selection
This product is a halogenated aromatic building block, not a solvent. Solvent choice pertains to its use in synthesis.
Sparingly soluble in water; readily soluble in nonpolar to moderately polar organics (toluene, xylene, CPME, MTBE, THF, dioxane, DMF/DMAc/NMP, and chlorinated solvents).
Low dielectric constant media (toluene, dioxane, ethers) often favored for Pd-catalyzed cross-couplings of aryl chlorides; polar aprotics (DMF/DMAc) can accelerate reactions but complicate workup.
Selection guidance by transformation (literature):
Suzuki–Miyaura: 1,4-dioxane/water or toluene/water biphasic with base (K3PO4, Cs2CO3). Add TBAB or PEG phase-transfer if needed.
Buchwald–Hartwig amination: toluene or xylene with bulky phosphine ligands (SPhos/XPhos/BrettPhos); or dioxane and tert-amines as base.
Halogen–magnesium exchange (Turbo Grignard): THF at −78 to 0 °C; rigorously anhydrous.
Lithiation/metalation: ethers (THF, MTBE) at cryogenic temperatures if feasible.
Practical comparisons (literature):
Toluene vs dioxane: toluene is easier to remove and greener score can be better; dioxane often increases rates for aryl chlorides.
THF vs 2-MeTHF: 2-MeTHF provides similar reactivity with better safety/green metrics and easier phase splits.
Always pre-test solvent compatibility with catalysts/ligands and confirm substrate solubility at target concentrations.
Storage and Reconstitution
Storage (item-specific): Store at room temperature (as provided in Product Data). Ship under normal conditions.
Container: Keep tightly closed in a compatible, chemically resistant container (e.g., amber glass) to minimize vapor loss and prevent contamination.
Atmosphere: Typically stable in air; for moisture- or oxygen-sensitive applications (e.g., metalation), dispense and store under dry inert gas after opening to maintain low water content.
Light: Standard laboratory lighting is acceptable; optional light protection is prudent for long-term storage of halogenated aromatics.
Stability: Halogenated benzenes are generally stable; avoid prolonged exposure to strong UV, strong bases, or reactive metals unless intended.
Reconstitution: Not applicable—use neat as a liquid. If material becomes viscous or partially solid at low temperatures, gently warm to ambient and mix before use.
Handling after opening: To maintain quality for sensitive reactions, consider aliquoting under inert atmosphere and storing in a desiccator or dry cabinet. Record open date and lot for traceability.
Disposal: Treat as halogenated organic waste; dispose according to institutional and regulatory requirements.
For any item-specific specifications (assay, water, inhibitors), and shelf-life/expiry, consult the CoA/Spec Sheet and SDS.
Structure and Identity
Brief description: 2,5-Dichlorofluorobenzene is a polyhalogenated benzene bearing two chloro substituents and one fluoro substituent on an aromatic ring; useful as an orthogonally reactive aryl halide building block.
Item-specific (from Product Data)
Product name: 2,5-Dichlorofluorobenzene
CAS: 348-59-4
PubChem CID: 136173
InChIKey: 26650 (as provided)
Storage conditions: Room temperature; shipped under normal conditions
Research use: For research use only
Literature/Computed identifiers and features (general reference; not item specifications)
SMILES (one of several valid depictions): Fc1cc(Cl)ccc1Cl (literature)
Structural features: planar benzene ring with three deactivating, o/p-directing halogens; F at position 1, Cl at positions 2 and 5 (1,2,5-substitution pattern). No stereocenters; aromatic π-system.
Functional groups: aryl C–F and two aryl C–Cl bonds; no heteroatoms beyond halogens; nonpolar/aromatic core.
2D structure description in words (literature)
Take a benzene ring; place F at position 1. Adjacent (ortho) to F at position 2 is Cl; across the ring at position 5 (para to position 2, meta to F) is another Cl. The remaining ring positions are unsubstituted hydrogens.
Synthetic Utility
Key reactivity features (literature):
Dual aryl chlorides: amenable to Pd-catalyzed cross-coupling (Suzuki, Buchwald–Hartwig, Sonogashira, Negishi, Kumada) with suitable ligands (SPhos/XPhos/RuPhos/BrettPhos). Allows sequential or differential functionalization.
Aryl fluoride: Relatively inert under many coupling conditions, serving as a protecting/retentive handle or for later activation via specialized catalysis (e.g., Ni, photoredox) or directed metalation/trifluoromethylation strategies.
Strategic applications (literature):
Regioselective diversification: Exploit steric/electronic differences between 2- and 5-chloro positions to install amines/aryl/alkyl groups in a controlled order.
Late-stage transformations: Attempt C–F borylation or defluorinative functionalization with bespoke catalysts, or convert C–F to C–H via hydrodefluorination in which C–Cl remains protected (or vice versa under orthogonal conditions).
Metalation chemistry: Halogen–magnesium exchange (i-PrMgCl·LiCl in THF) or directed ortho-metalation relative to F can generate arylmetals for electrophile trapping; conditions must be rigorously anhydrous and temperature-controlled.
Limitations (literature):
SNAr generally poor without strong ring activation; base-promoted substitutions usually fail or require extreme conditions.
Direct Grignard formation from aryl chlorides can be sluggish; activating metals (Rieke Mg), ultrasound, or halogen–magnesium exchange strategies are preferred.
Analytical: Monitor reactions by GC or LC–MS; characteristic isotope pattern from two chlorines aids MS identification (M, M+2, M+4).
Target Specificity
Not applicable. This product is a small-molecule building block and does not exhibit biomolecular target specificity, nor does it have attributes such as clone, isotype, or species reactivity associated with biologics. Refer instead to the Synthetic Utility and Reaction & Applications sections for relevant use information.
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