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
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
207.010 g/mol
XLogP3
2.900
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
205.954 Da
Monoisotopic Mass
205.954 Da
Topological Polar Surface Area
57.500 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
185.000
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
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Application Protocols
No application protocols are specified for this SKU. As a small-molecule building block, procedures will depend on your synthetic objective.
General starting points (guidance only):
Preparing the methyl ester (analytical reference standard): Dissolve the acid in methanol with a catalytic drop of conc. H2SO4; stir at 60–65 °C for 4–6 h; neutralize, extract with EtOAc, wash, dry, and concentrate; purify by silica.
EDC-mediated amidation (library synthesis): In dry DMF, combine acid (1.0 eq), amine (1.2 eq), EDC·HCl (1.2 eq), Oxyma (1.2 eq), and DIPEA (3 eq) at rt for 12 h; quench with water and extract; or precipitate the product by water addition if applicable.
Pd-catalyzed diversification (after ester protection): For Suzuki, combine aryl chloride (1.0 eq), boronic acid (1.3 eq), Pd-precatalyst (1 mol% Pd) with SPhos (2 mol%), K3PO4 (3 eq), 2‑MeTHF/H2O (9:1), 90 °C for 8 h; work up and saponify the ester if free acid is desired.
Always tailor stoichiometry, temperature, and purification to your substrate scope and consult primary literature for analogous salicylate derivatives.
Biological Roles
Item-specific biological/biochemical roles are not provided for this SKU and, as a synthetic research chemical, it is supplied strictly for laboratory use.
General context (literature):
Salicylate motif: The 2‑hydroxybenzoate framework is known to form chelates with metal ions and to participate in hydrogen‑bond networks, properties often exploited in biochemical probes and coordination chemistry. Chlorination alters lipophilicity and acidity relative to salicylic acid.
Ionization behavior: At physiological pH, the carboxylate is favored; phenolic OH may remain largely unionized (pKa >> 7). This can influence membrane interaction in model systems, but no endogenous role is established for this dichloro derivative.
Enzyme binding (general observations): Salicylates can associate with proteins via H-bonding and ionic interactions; however, specific target engagement for 4,5-dichloro-2-hydroxybenzoic acid has not been established in the public literature.
Use limitations:
This material is not intended for clinical, diagnostic, or in vivo therapeutic use. Any biological experiments should be conducted under appropriate approvals and controls, and results interpreted with caution due to potential off-target effects of halogenated aromatics.
Buffer Applications
This compound is not commonly employed as a laboratory buffer. Its principal pKa (carboxylic acid) is expected in the ~2.2–2.6 range for dichloro-salicylates (literature estimate), which lies outside the conventional buffering windows used for most biochemical assays.
Practical notes:
If used at all, buffering capacity would be confined to acidic ranges near pH 2–3, which is rarely desirable for biological systems.
For low‑pH buffering, consider established systems such as glycine/HCl, citrate, or phosphate mixtures depending on the target pH window.
The compound may be used as an analyte or additive in buffer systems (e.g., to probe binding or solubility), but it is not a standard buffer component.
Conclusion: Select buffering agents with well‑characterized pKa values in your experimental pH range and documented compatibility with your biological or analytical method.
Green Alternatives
While the substrate itself is fixed, you can reduce process impact by selecting greener reagents, solvents, and activation strategies when working with 4,5-dichloro-2-hydroxybenzoic acid.
Greener choices (general guidance):
Solvents: Favor 2‑MeTHF or Cyrene/EtOAc over DMF/NMP where feasible. For esterifications, MeOH/EtOH are preferable to chlorinated solvents. For extractions/crystallizations, use EtOAc/IPA in place of DCM.
Coupling reagents: Replace DCC/HOBt (sensitizer/explosive risk) with EDC·HCl + Oxyma Pure or CDI. These reduce urea waste and hazard.
Catalysis: For aryl chloride couplings (after acid protection), deploy ligand-optimized Pd catalysts at low loadings (≤1 mol%) and consider aqueous micellar media (TPGS-750-M) to cut organic solvent use.
Energy: Perform room-temperature couplings where possible; use flow or microwave to shorten times and improve selectivity.
Trade-offs:
2‑MeTHF/EtOAc may offer lower solubility for the neutral acid than DMF/DMSO—optimize temperature or employ a base to form soluble carboxylates transiently.
CDI and EDC routes can be moisture-sensitive; enforce good drying practices.
Greener: 2‑MeTHF or EtOAc + EDC/Oxyma or CDI → comparable yields, simpler workup, reduced hazard profile.
Always confirm that greener substitutions meet your reaction performance, impurity, and scalability targets.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation grade is specified for this item. It is supplied for research use only.
General context (non-clinical, literature):
Synthetic intermediate: The salicylate core and aryl chlorides make this compound a useful building block for preparing salicylamides, esters, and diversified aryl derivatives that can be screened in medicinal chemistry. Any such use remains at the discovery/research stage unless supported by appropriate regulatory data.
Salt forms: Carboxylate salts (e.g., sodium/potassium) may be generated to increase aqueous solubility for process operations, not for administration.
Impurity profiling: For potential GMP trajectories, control of residual metals (from Pd catalysis), chlorinated byproducts, and coupling reagent residues would be essential, but no such controls are specified for this SKU.
Compliance note:
Do not use in human or veterinary applications. For any work toward regulated use, source GMP-grade starting materials and establish full analytical controls per ICH guidelines; this catalog item does not claim such status.
Physical Properties
Item-specific physico-chemical specifications (mp, bp, density, UV cutoff, metal content, etc.) are not provided here. Always consult the item’s CoA/Spec Sheet for definitive values.
Literature/general expectations for 4,5-dichloro-2-hydroxybenzoic acid and close analogs (for guidance only; verify experimentally):
Physical state: Typically a crystalline solid (literature; specific appearance for this item not specified).
Melting point: Halogenated salicylic acids commonly melt in the ~200–230 °C range; reported values for dichloro derivatives often lie near the lower half of this band (literature/approximate; confirm before use).
Boiling point: Not meaningful due to decomposition; salicylic-type acids generally decompose before boiling at 1 atm (literature).
Acidity (pKa): Salicylic acid pKa1 ~2.97; ring chlorination increases acidity. Dichloro substitution at 4,5 is expected to lower pKa into roughly ~2.2–2.6 (literature estimate for related compounds).
LogP/partitioning: Electron-withdrawing chlorines increase hydrophobicity; unionized form expected to have moderate logP, while the carboxylate is water-soluble at basic pH (literature trend).
Solubility: Sparingly soluble in water at neutral pH; improved solubility in alcohols (MeOH, EtOH), acetone, acetonitrile, ethyl acetate, and in aqueous base via deprotonation (literature behavior). Intramolecular H-bonding can reduce polarity of the neutral form.
Refractive index/density/vapor pressure: Not generally reported for solids of this type (not specified for this item).
Practical note: For preparative work, measure an experimental solubility and pKa under your conditions; halogenation and intramolecular H-bonding can shift these parameters appreciably.
Quality and Grades
Item-specific grade/purity and stabilizer information are not provided for this SKU. Do not assume assay, metal content, water content, or chromatography suitability; consult the CoA/Spec Sheet for definitive quality attributes.
Guidance on typical grades and what they imply (general):
Analytical/AR grade: Suitable for analytical workflows; tighter controls on inorganic and organic impurities.
Synthesis grade: Intended for routine organic synthesis where minor impurities are acceptable.
HPLC/UV grades (solvents): Not applicable to this solid; for solids, a “>98%” or “>99%” assay is more typical when specified.
Considerations specific to halogenated salicylic acids:
Residual halides and metals: If cross-couplings or metal-catalyzed steps are planned, low metal background can matter; request ICP data if relevant to your process.
Water content: Moisture can impact coupling efficiency (EDC/DIC) and acyl chloride generation. If Karl Fischer is critical to your application, request a measured value.
Particle size: Crystallinity and particle size can affect dissolution and filtration; ask for sieve data when scale-up or formulation is planned.
Recommendation: For sensitive transformations (e.g., Buchwald coupling on aryl chloride, or amide coupling destined for impurity-critical routes), obtain the latest CoA and, if necessary, request a lot reservation with accompanying analytical package (NMR, HPLC, KF, ICP) aligned to your internal specifications.
Reaction and Applications
As a dichloro-substituted salicylic acid, this compound serves as a versatile building block combining an aryl chloride manifold, a phenolic OH, and a carboxylic acid. Typical research applications include:
Esterification and Amidation: Convert the acid to esters (Fischer or Steglich) and amides (EDC/HOBt, DIC/Oxyma) to generate salicylate derivatives. The ortho-OH permits intramolecular H-bonding in products, influencing conformation and binding.
Acyl Chloride Intermediate: Activation with SOCl2 or (COCl)2 (cat. DMF) furnishes the acid chloride for downstream acylations under mild conditions.
Metal Coordination/Materials: The o-hydroxybenzoate motif is a classic chelating ligand (O,O′ donor). Deprotonated forms can build coordination complexes and metal–organic frameworks; chloro substituents modulate electronics and packing.
Cross-Coupling at Aryl Chlorides: After masking the acid (e.g., methyl/tert-butyl ester), the 4,5-dichloro ring can undergo Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira couplings using Pd catalysts/ligands optimized for aryl chlorides (e.g., SPhos/XPhos systems), enabling rapid diversification.
Protection/Functional Group Interplay: The phenol can be protected (e.g., benzyl, MOM, silyl) to steer chemoselectivity during cross-couplings or electrophilic steps.
SNAr Considerations: The ring is deactivated; without additional strong EWGs (e.g., –NO2), SNAr at chloro positions is generally disfavored.
Practical tips:
Dry solvents and control moisture for coupling efficiency. For cross-coupling, esterify the acid first to avoid base-promoted decarboxylation or catalyst inhibition. Monitor intramolecular H-bond effects on NMR and chromatographic behavior.
Reaction Conditions
Representative literature-style conditions for common transformations of 4,5-dichloro-2-hydroxybenzoic acid (verify and optimize for your system):
Fischer Esterification: Acid + ROH (5–10 eq), H2SO4 (cat.) or p‑TsOH, 60–80 °C, 4–16 h. Remove water (Dean–Stark for higher alcohols). Typical isolated yields: 70–90% for salicylates.
Steglich Esterification: Acid, alcohol/phenol (1.1–1.5 eq), DCC or DIC (1.1–1.5 eq), DMAP (5–10 mol%), CH2Cl2 or EtOAc, 0 °C → rt, 2–12 h. Filter urea byproduct; 70–95%.
Amide Coupling: Acid, amine (1.1–1.5 eq), EDC·HCl (1.1–1.5 eq) + Oxyma/HOAt, DIPEA (2–3 eq), DMF/MeCN, rt–40 °C, 2–18 h. 70–95%.
Acid Chloride Formation:SOCl2 (3–5 eq), catalytic DMF, reflux 1–3 h; remove volatiles, quench to isolate acid chloride or carry forward in situ.
Buchwald–Hartwig Amination (on aryl chloride, ester-protected acid): Aryl chloride (1.0 eq), amine (1.2 eq), Pd2(dba)3 (1–2 mol% Pd), SPhos (2–4 mol%), base NaOtBu or K3PO4, solvent 1,4‑dioxane or toluene, 90–110 °C, 6–16 h. 60–90% typical for activated systems.
Suzuki–Miyaura (ester-protected): Aryl chloride (1.0 eq), boronic acid/ester (1.2–1.5 eq), Pd(PPh3)4 or Pd-precatalyst + XPhos/SPhos (1–2 mol% Pd), base K3PO4 or Cs2CO3, solvent 2‑MeTHF or dioxane/H2O (9:1), 80–100 °C, 4–12 h. 60–90%.
Notes:
Protect or convert the acid to an ester prior to strong base/coupling to avoid salt formation and catalyst inhibition.
Intramolecular H‑bonding can affect reactivity; DMAP or stronger bases may be needed to activate the phenol for O‑acylation/alkylation.
Safety and Handling
Item-specific GHS classification, H-statements, and pictograms are not provided here. Defer to the product SDS for authoritative safety data and regulatory classification.
General safety considerations for halogenated salicylic acids (informational guidance only):
Hazard profile: Organic acids can be irritating to skin, eyes, and respiratory tract. Halogen substitution may increase lipophilicity and irritation potential. Avoid dust formation and inhalation.
PPE: Wear lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use a dust mask/respirator if airborne particulate may be generated (per SDS/OSHA guidance).
Engineering controls: Handle powders in a fume hood or ventilated enclosure. Employ closed transfer or dampen solid to minimize dust.
First aid (overview): Flush eyes/skin with water for 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention. Follow SDS instructions.
Storage incompatibilities: Keep away from strong bases (will form carboxylate salts), strong oxidizers, and acylation/halogenating reagents unless intended. Avoid contact with reactive acyl chloride-forming agents without controls.
Thermal stability: Aromatic acids are generally thermally robust but may decompose on strong heating; avoid grinding-induced heating.
Environmental note: Prevent release to the environment; halogenated aromatics can be persistent.
Emergency response and waste: Collect spills with inert absorbent; dispose of waste following local regulations for halogenated organic solids. Always prioritize the SDS for this specific SKU.
Solvent Selection
This product is a solid aromatic carboxylic acid, not a solvent. Solvent selection revolves around dissolving the substrate for synthesis, crystallization, or analysis.
General solvent compatibility (literature guidance):
Water: Low solubility at neutral pH; readily soluble as the carboxylate in basic aqueous media (e.g., NaHCO3/Na2CO3/NaOH).
Polar protic:Methanol, ethanol, isopropanol often dissolve the neutral form upon heating; useful for Fischer esterification and recrystallization selections.
Polar aprotic:DMF, DMSO, NMP, acetonitrile provide strong solvating power for coupling reactions (EDC/DIC) and for NMR (DMSO‑d6).
Moderately polar aprotic/ethers/esters:Acetone, ethyl acetate, 2-MeTHF, CPME can dissolve the neutral form to varying extents; EtOAc and 2-MeTHF are good workup/recrystallization choices.
Selection tips:
Couplings (amide/ester): DMF/MeCN (homogeneous), or 2‑MeTHF/EtOAc with carbodiimides if solubility allows.
Acyl chloride formation: Use neat thionyl chloride or oxalyl chloride with catalytic DMF; product often precipitates upon quench.
Cross-coupling on aryl chloride (after protecting the acid as an ester):1,4-dioxane, toluene, 2‑MeTHF with aqueous base are common media.
Crystallization: Explore EtOAc/hexane, IPA/water, or EtOAc/MTBE systems to tune purity and particle size.
Always confirm actual solubility for your lot and temperature; intramolecular H-bonding can lower apparent polarity of the neutral form and affect solvent choice.
Storage and Reconstitution
Item-specific storage condition: Room temperature (as provided). Shipment: Normal (as provided). No stabilizers or reconstitution instructions are specified for this SKU.
Best practices for solids of this class:
Container: Store in a tightly closed container to minimize moisture uptake and contamination. Use amber glass if prolonged light exposure is expected, although the compound is not highly photosensitive.
Environment: Keep in a cool, dry place. A desiccator or dry cabinet is recommended for long-term storage to preserve assay and handling characteristics.
Handling: Allow the sealed container to equilibrate to room temperature before opening to avoid condensation. Reseal promptly after use.
Solution preparation: Dissolve in a suitable dry organic solvent (e.g., DMSO, DMF, MeOH, EtOAc) or in aqueous base to form the carboxylate as needed. Filter sterilize through 0.22 µm if a sterile solution is required for assay setups.
Shelf life: Not specified for this item; refer to CoA/Spec Sheet. If preparing stock solutions, store aliquots at low temperature (e.g., 2–8 °C for short term or −20 °C for longer term) and avoid repeated freeze–thaw cycles.
Always refer to the product’s label and CoA/SDS for definitive storage guidance and any lot-specific precautions.
Structure and Identity
A halogenated salicylic acid derivative featuring a phenolic OH and a carboxylic acid on an ortho-related benzene ring substituted with two chlorines.
Product name (item-specific): 4,5-Dichloro-2-hydroxybenzoic acid
CAS (item-specific): 50274-58-3
CID (item-specific): 23046755
InChIKey (item-specific): 203499 (as provided)
SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (literature/computed): C7H4Cl2O3 (salicylic acid core with two ring chlorines)
Core ring system: Benzene ring bearing adjacent (ortho) functionalities: a phenolic hydroxyl (–OH) at C-2 and a carboxylic acid (–CO2H) at C-1 (salicylic acid motif).
Halogen substituents:Chloro groups at C-4 and C-5, rendering the ring deactivated toward electrophilic substitution and enabling potential cross-coupling at aryl chloride positions under appropriate Pd catalysis.
Functional group topology: The o-hydroxy–carboxylic acid arrangement supports intramolecular O–H···O=C hydrogen bonding, influencing acidity, tautomer preferences, and solid-state packing.
Canonical identifiers beyond those listed are not specified for this item. A representative literature SMILES for this structure is typically reported for 4,5-dichloro-salicylic acid; verify against the product CoA/SDS if needed.
Synthetic Utility
The molecule’s combination of a carboxylic acid, phenolic OH, and two aryl chlorides provides multiple orthogonal handles for divergent synthesis:
Acid transformations:
Esterification: Fischer (alcohol + acid catalyst) or Steglich (DCC or DIC + DMAP) to give salicylate esters.
Amidation: EDC·HCl/Oxyma or HATU for amide libraries; intramolecular H‑bonding often stabilizes conformers.
Acid chloride: SOCl2/(COCl)2 to access acylations and peptide couplings.
Phenol chemistry:
Protection: MOM, benzyl, or silyl groups to control selectivity and improve cross-coupling performance.
O‑alkylation/acylation: Williamson ether synthesis (after deprotonation) or acylations to modulate electronics and solubility.
Aryl chloride diversification:
Suzuki–Miyaura: With boronic acids/esters; SPhos/XPhos or BrettPhos ligands facilitate activation of aryl chlorides.
Buchwald–Hartwig amination: Formation of anilines/diarylamines under Pd catalysis (protect acid first to avoid base incompatibility).
Sonogashira/Heck: Alkyne or olefin installation to access extended π-systems; again, protect/esterify the acid.
Directed strategies: Carboxylate and phenol can direct ortho‑metalation or C–H activation in advanced methods (often requiring temporary protection/derivatization).
Retrosynthetic value: As a readily available dichloro-salicylate node, it enables late‑stage diversification while leveraging intramolecular H‑bonding for conformational control, useful in both small‑molecule probe and ligand design.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biologic or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
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