This compound belongs to the class of organic compounds known as dichlorobenzoic acids. These are benzoic acids having two chlorine atoms attached to the carboxylated benzene ring.
External Descriptors
dichlorobenzene - chlorobenzoic acid
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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Recensioni
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Application Protocols
Not applicable to this product type
No WB/IHC/IF/FC or related biological assay protocols are defined for this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Application notes above.
General laboratory usage tips (chemistry)
Prepare concentrated stock solutions in DMSO, DMF, MeOH, or EtOAc if needed; record exact concentrations gravimetrically.
For acid chloride preparations or couplings, perform small-scale trials to optimize ligand/base/solvent prior to scale-up. Monitor by TLC/HPLC at 254 nm.
Biological Roles
Scope of this section
This product is a small-molecule aromatic carboxylic acid intended for research and synthesis. No medical or clinical uses are implied.
General biochemical context (literature/general)
Benzoic acid derivatives can interact with biological membranes depending on lipophilicity and pKa. The 2,6-dichloro substitution increases hydrophobicity and lowers pKa relative to benzoic acid, which can affect partitioning between aqueous and lipid phases and the degree of ionization at physiological pH.
Carboxylic acids are typically metabolized via conjugation pathways (e.g., glucuronidation, glycine conjugation) in biological systems. Chlorinated aromatics may display slower biodegradation than non-halogenated analogs, with environmental persistence considerations.
No specific role as a metabolite, cofactor, or ligand is commonly assigned to 2,6-dichlorobenzoic acid in biochemistry literature; it is primarily a synthetic intermediate or probe molecule in physico-chemical studies.
Usage note
If used in biological assays, ensure appropriate solubilization (e.g., DMSO stocks diluted into buffer), minding final DMSO content and pH-dependent ionization. Validate potential assay interference from aromatic acids (e.g., UV absorbance at 210–254 nm) and consider vehicle-only controls.
Buffer Applications
Not typically applicable
2,6-Dichlorobenzoic acid is not commonly used as a buffer component. Its relatively low pKa (~2.7–2.9, literature) and limited aqueous solubility at neutral pH make it unsuitable for most biological buffer ranges.
Practical guidance
For buffer systems near pH 2–3, standard buffer components (e.g., citrate, phosphate at lower pH limits) are strongly preferred due to well-characterized buffering capacity and compatibility.
If the compound is included in an assay matrix, prepare it as a DMSO or ethanol stock and dilute into the desired buffer, verifying that final pH and cosolvent content meet your assay specifications.
Green Alternatives
Green chemistry perspective (general)
Halogenated aromatics have potential persistence and higher EHS footprints. Where feasible, consider non-halogenated or mono-halogenated analogs if they meet performance criteria. However, the 2,6-dichloro motif is often function-critical (sterics/electronics), limiting substitution.
Alternatives and tradeoffs (literature/general)
Benzoic acid (non-halogenated): Greener, widely available, lower environmental impact. Tradeoff: Loss of electron-withdrawing character and steric hindrance; different reactivity and physicochemical properties (higher pKa, greater water solubility of salts, lower logP).
2-Chlorobenzoic acid (mono-chloro): Intermediate compromise on EHS and properties; still less steric hindrance than 2,6-dichloro and altered reactivity/selectivity.
Process intensification: If the dichloro acid is essential, emphasize greener solvents (e.g., 2-MeTHF, CPME, bio-ethanol) for esterification/coupling, and adopt catalytic, room-temperature coupling protocols (micellar catalysis, photoredox) to cut energy and solvent use.
Function retention: 2,6-dichloro > mono-chloro > benzoic acid (steric/electron-withdrawing effects)
Practical guidance
Optimize atom economy via decarboxylative couplings or direct C–H functionalization to reduce prefunctionalization steps.
Employ solvent recycling and salt-minimizing workups (e.g., solvent swaps over aqueous neutralizations) where compatible with downstream specifications.
Pharmaceutical Uses
Formulation/manufacturing context (no therapeutic claims)
Role: Primarily a synthetic intermediate for generating 2,6-dichlorobenzoyl derivatives (acid chlorides, esters, amides) used in medicinal chemistry campaigns and fine chemical synthesis.
Excipient status: Not commonly used as a pharmaceutical excipient. No pharmacopeial monograph is cited here for this specific dichloro isomer; consult compendia if required.
Process considerations (general)
Upstream building block: Facilitates structure–activity exploration where ortho sterics/electron withdrawal are essential. Conversion to the acid chloride enables acylation of amines/alcohols to furnish target APIs/intermediates.
Purification: The acid/base properties aid in phase-split workups, improving throughput in medicinal chemistry platforms. Crystalline nature supports robust isolation and solid form control for intermediates.
Residuals and control: If used in GMP-related routes, establish tight specifications for assay, related substances (including isomeric chlorobenzoic acids), residual chlorinating reagents (if acid chloride used), and neutralization byproducts. Analytical methods typically include HPLC-UV and GC for solvents.
Green/process safety
Consider greener coupling conditions (aqueous micellar catalysis, enzymatic esterifications) when compatible. Account for potential environmental persistence of chlorinated aromatic residues in waste streams; implement appropriate treatment and solvent recovery.
Physical Properties
Item-specific (Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Computed/Literature values (for reference; not item-specific specifications)
Melting point: Typically ~196–200 °C (literature range for 2,6-dichlorobenzoic acid; crystalline solid)
Boiling point: Not commonly reported due to decomposition; benzoic acids generally decompose before distillation at atmospheric pressure (literature note)
pKa (carboxyl): ~2.7–2.9 in water at 25 °C (literature; electron-withdrawing Cl groups lower pKa vs. benzoic acid ~4.2)
LogP (neutral acid): Expected in the ~2.5–3.0 range (literature/estimations for dichloro-substituted benzoic acids)
Solubility: Sparingly soluble in water at neutral pH (carboxylic acid form); increased solubility as the benzoate salt at basic pH; readily soluble in polar organic solvents such as acetone, acetonitrile, ethyl acetate, methanol, ethanol, isopropanol, DMSO, and DMF (literature, qualitative).
Vapor pressure: Very low for a polyfunctional aromatic acid; not typically significant at room temperature (literature expectation).
Refractive index: Not applicable to a crystalline solid.
Notes for practitioners
The ortho dichloro substitution raises lattice energy and melting point compared with benzoic acid.
Salt formation with bases (e.g., NaHCO3, NaOH) is a practical way to enhance aqueous handling and purification (acid-base extraction).
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on quality considerations (general)
Identity confirmation: For aromatic acids, identity is routinely verified by 1H/13C NMR (characteristic downfield carboxyl proton if not exchanged), IR (broad O–H stretch ~2500–3300 cm−1, C=O ~1680–1725 cm−1), and HRMS/GC-MS/LC-MS. Melting point is a useful orthogonal check for crystalline materials like 2,6-dichlorobenzoic acid.
Purity assessment: HPLC/UPLC with UV detection at 210–230 nm and 254 nm typically provides clean profiling. Residual solvents and volatile impurities can be assessed by GC; water content by Karl Fischer (for hydrate/moisture assessment if relevant). Halide-containing impurities and isomeric chlorobenzoic acids may be potential related substances.
Stabilizers: Not typically required for benzoic acids; none specified for this item. If stabilizers are present in other offerings, they are intended to maintain long-term assay or inhibit polymorphic changes—always check the CoA.
Heavy metals/halide content: If your method is sensitive to trace metals or halides (e.g., in cross-coupling catalysis), request trace analysis data. Inhibitory chloride is inherent to structure but trace metal contamination should be minimal with high-quality lots.
Suitability by application: For demanding synthesis (e.g., pharmaceutical intermediates), specify assay, related substances profile, and residual solvent limits. For analytical uses, consider an assay ≥99% with well-defined impurity thresholds and a tight MP range. Always confirm lot-specific specifications on the CoA.
Reaction and Applications
Typical uses in synthesis (literature/general)
Precursor to acyl derivatives: Conversion to 2,6-dichlorobenzoyl chloride using SOCl2 or (COCl)2 provides a hindered acylating agent useful in selective acylations where sterics are beneficial.
Ester and amide formation: Employed in Fischer esterifications (acidic alcoholysis) and in peptide/amide couplings (EDC/HATU/DCC). The ortho dichloro pattern influences conformations and can modulate amide rotational barriers.
Decarboxylative functionalization: Benzoic acids participate in decarboxylative cross-couplings (photoredox/Ni dual catalysis, Ag-assisted, or electrochemical) to generate aryl radicals leading to C–C or C–heteroatom bond formation. Electron-deficient, chloro-substituted arenes often show favorable reactivity profiles.
Cross-coupling at aryl chloride sites: The two aryl chlorides serve as handles for Pd- or Ni-catalyzed transformations (Suzuki–Miyaura, Buchwald–Hartwig, Buchwald etherification). Modern ligand systems enable coupling of aryl chlorides; the carboxyl group can be protected (as ester or converted to acid chloride/anhydride) depending on conditions.
Directed ortho chemistry: Although 2,6-dichloro deactivates EAS, the carboxyl group can direct metalation under strong bases (e.g., LDA, s-BuLi with TMP) to access further substitution, acknowledging steric congestion.
Application domains (non-clinical)
Fine/intermediate synthesis: Building block for agrochemical and materials intermediates where steric and electronic tuning from o,o-dichloro substitution is desired.
Crystalline derivatives: Used to engineer solid-state properties (melting points, cocrystals) through halogen bonding and hydrogen-bond donor/acceptor interplay.
Reaction Conditions
General conditions (literature guidance; adjust per substrate/scope)
Acid chloride formation: SOCl2 (3–5 equiv) with catalytic DMF, 0–25 °C to reflux (65–80 °C) for 1–3 h; or oxalyl chloride (2–3 equiv) in DCM at 0–25 °C. Off-gas HCl/CO/CO2 as appropriate; employ a scrubber. Typical isolations are high-yielding for benzoic acids.
Steglich esterification: Alcohol (1.5–3 equiv), DCC (1.1–1.5 equiv), catalytic DMAP in DCM (0–25 °C), 2–16 h. Filter DCU; 70–95% yields commonly reported for benzoic acids bearing EWG substituents.
Fischer esterification: Acid-catalyzed (H2SO4 or p-TsOH), refluxing toluene or neat alcohol with Dean–Stark or drying agent, 4–24 h. Equilibrium-driven; remove water for high conversion.
Amidation (carbodiimide/uronium): EDC·HCl (1.1–1.5 equiv) with HOBt analog or Oxyma and base (DIPEA) in DMF/DCM, 0–25 °C, 1–12 h. HATU/HBTU variants offer faster kinetics.
Suzuki–Miyaura coupling (aryl Cl): Pd(0/II) with bulky, electron-rich phosphines (e.g., XPhos, SPhos, t-Bu3P) or NHC ligands; base (K3PO4, K2CO3), toluene/dioxane/IPA–water (60–110 °C). The 2,6-dichloro pattern may require elevated temperature or tailored ligands; sequential mono-coupling often achievable.
Decarboxylative coupling: From NHPI ester under photoredox/Ni dual catalysis (e.g., Ir[dF(CF3)ppy]2(dtbbpy)PF6 + NiCl2·glyme, blue LEDs), EtOAc/DMF or MeCN, rt to 40 °C, 4–24 h; productivity substrate-dependent.
Workup/purification
Exploit acid/base extraction for acid vs. neutral products. For acyl chlorides, quench cautiously. Recrystallization affords high purity; chromatographic purification may require base-deactivated silica for acid-sensitive derivatives.
Safety and Handling
Item-specific (Product Data)
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
Hazard (H-) Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
Research Use Note: For research use only.
General safety information (literature/best practice; not a substitute for the SDS)
Likely hazards: Aromatic carboxylic acids and chlorinated arenes are commonly classified as irritants; avoid inhalation of dust and contact with skin/eyes. Some chlorinated aromatics may be hazardous to aquatic environments—prevent environmental release.
PPE: Wear lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (nitrile commonly suitable). Use a dust mask/respirator if dust generation cannot be controlled (consult SDS for limits).
Handling: Minimize dust; handle in a fume hood during weighing, transfers, and especially during conversion to acid chloride (if performed) due to evolved HCl.
Incompatibilities: Strong bases will form benzoate salts (heat generation possible on neutralization). Avoid contact with strong oxidizers. If preparing acyl derivatives, thionyl chloride/oxalyl chloride reagents require anhydrous conditions and proper off-gas scrubbing.
First aid (overview): Skin/eye contact—rinse with water for ≥15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical advice. Always follow facility SOPs and SDS instructions.
Fire response: Solid combustible organic; use CO2, dry chemical, or foam. Thermal decomposition may release HCl and other corrosive fumes.
Spill response: Avoid dust; sweep up gently, place in suitable container; wash area with detergent while preventing entry to drains.
Solvent Selection
Relevance to this compound type
2,6-Dichlorobenzoic acid is a moderately lipophilic aromatic carboxylic acid. Solvent choice drives solubility, reaction rates (particularly for acylation/esterification/amidation), and crystallization behavior.
Limited in: Water at neutral pH. Forms soluble benzoate salts in basic aqueous media (e.g., NaHCO3, Na2CO3, NaOH).
Crystallization: Frequently crystallized from EtOAc/hexanes, toluene, or alcohol/water mixtures. Ortho-dichloro substitution favors higher MP and good crystallinity.
Choosing solvents by task
Coupling/Amidation: DMF, NMP, or DCM with carbodiimide (EDC, DCC) or uronium reagents (HATU, TBTU). Add bases like DIPEA; include HOAt/HOBt analogs per safety policies.
Esterification: Fischer conditions in toluene or benzene surrogates (e.g., toluene) with azeotropic water removal; or DCM/DMF under Steglich conditions.
Acid chloride formation: Anhydrous DCM, toluene, or neat SOCl2/oxalyl chloride; catalytic DMF often accelerates.
Purification: Acid-base extraction using bicarbonate/carbonate for benzoate formation (aqueous), then re-acidify and extract into an organic phase; final trituration or recrystallization.
Comparison with alternatives
Relative to benzoic acid, the dichloro analog requires stronger or more polar solvents to achieve similar solubility; however, it often provides cleaner crystallization and higher recovery due to hydrophobicity and higher lattice energy.
Storage and Reconstitution
Item-specific (Product Data)
Storage Conditions: Room temperature.
Shipped In: Normal.
General guidance (literature/best practice)
Container: Store in a tightly closed container, protected from moisture to prevent caking and from base vapors that could lead to salt formation on the surface. Amber glass is prudent to limit any long-term photochemical discoloration, although the compound is generally photostable as a solid.
Shelf life: Aromatic carboxylic acids are typically stable for years at ambient conditions when kept dry and sealed. Verify lot-specific retest/expiry on the CoA.
Reconstitution/solubilization: Dissolve in organic solvents such as DMSO, DMF, acetone, acetonitrile, ethyl acetate, methanol, ethanol, isopropanol, THF, or dichloromethane. For aqueous work, first dissolve in a miscible organic solvent or form the benzoate salt by adjusting to basic pH (e.g., NaHCO3/NaOH), then dilute. Avoid strong bases if the free acid must be preserved.
Freeze–thaw: Not applicable to a solid. If preparing stock solutions, store aliquots to minimize freeze–thaw; DMSO or MeOH solutions are commonly kept at 2–8 °C or −20 °C per method needs.
Compatibility: Keep away from oxidizers and strong bases. If converting to acid chloride, conduct under anhydrous conditions with appropriate scrubbing of acidic off-gases.
Disposal: Follow institutional procedures for halogenated organic waste; avoid release to the environment.
Structure and Identity
Item-specific (Product Data)
SKU: D107594
Product Name: 2,6-Dichlorobenzoic Acid
CAS: 50-30-6
PubChem CID: 5758
Storage Conditions: Room temperature (as supplied)
Shipped In: Normal
Category Path: 全部 / 可售 / 化学和生化试剂
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/Literature identity (for reference; not item-specific specifications)
Core scaffold: A monosubstituted benzoic acid bearing two chloro substituents in the 2- and 6- (ortho, ortho) positions relative to the carboxyl group.
Functional groups: Arene (benzene ring), carboxylic acid (–CO2H), two aryl chlorides (–Cl) that are deactivating and ortho/para directing.
Sterics: The 2,6-dichloro substitution creates significant ortho crowding around the carboxyl, influencing reactivity (e.g., slower acylation, modified hydrogen-bonding, and altered crystallinity) and conferring hindered acyl derivatives when converted to acid chloride/anhydride.
Electronic effects: Each chlorine is moderately electron-withdrawing by induction and weakly donating by resonance, overall deactivating the ring toward electrophilic substitution while enabling metal-catalyzed cross-coupling from aryl chloride sites under appropriate conditions.
2D description in words: A benzoic acid ring with the –CO2H at position 1 and chlorine atoms at positions 2 and 6 (both ortho to the acid).
Synthetic Utility
Functional group leverage
Carboxylic acid: Versatile handle for esterification (Fischer, Steglich), amidation (EDC/HATU/DCC), anhydride and acid chloride formation, decarboxylative couplings, and late-stage diversification via Curtius/Schmidt-type rearrangements (from the corresponding acyl azide; observe safety rigor).
Aryl chlorides (2,6-positions): Serve as electrophilic sites for Pd/Ni-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig amination, Buchwald etherification). The 2,6-pattern induces steric hindrance that can promote mono-selectivity and influence catalyst/ligand choice.
Strategic value
Steric steering: The ortho dichloro motif provides a hindered benzoyl unit useful for tuning conformation, metabolic stability (in medicinal chemistry), and solid-state behavior. The hindered acid chloride can show altered reactivity/selectivity in acylations.
Protection/activation: Temporary masking as methyl/benzyl esters can enable orthogonal manipulations (e.g., cross-coupling on the ring) followed by deprotection (saponification or hydrogenolysis).
Decarboxylative routes: Redox-active esters (e.g., NHPI esters) derived from this acid engage in photoredox/Ni dual catalysis for C(sp2)–C and C(sp2)–heteroatom bond formation, bypassing preformed aryl organometallics.
Analytical/processing tips
Acid/base extraction streamlines removal of neutral/aromatic impurities. Recrystallization from EtOAc/hexanes or toluene/alcohol mixtures is effective; seed for consistent polymorph outcomes when required.
Monitor couplings at 254 nm; the dichloro arene exhibits strong UV absorbance, aiding HPLC tracking.
Target Specificity
Not applicable to this product type
This item is a small-molecule chemical reagent, not a biological macromolecule or antibody. No antigen/epitope, clone, isotype, or species reactivity data apply.
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