This compound belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.
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. No immunoassay or bioanalytical application protocols (WB, IHC, IF, FC) are provided for this small-molecule reagent.
For synthetic use, see the Reaction Conditions and Synthetic Utility sections for representative procedures and condition sets.
For analytical characterization, typical methods include 1H/13C NMR, GC/GC–MS, LC–MS, and IR; specific test methods and acceptance criteria should be taken from the CoA/Spec Sheet (not provided here).
Biological Roles
This product is provided for research use as a chemical building block; no biological/clinical uses are claimed for the SKU.
General notes (literature context):
Phenolic compounds can engage in hydrogen bonding and π–π interactions with biomolecules, but 2-chloro-6-methylphenol is primarily used as a synthetic intermediate rather than a biochemical reagent.
Halogenated phenols are sometimes studied as reference compounds for environmental fate, sorption, or biodegradation due to their amphiphilic nature and acidity; care should be taken to avoid extrapolating these general observations to specific biological effects.
The ortho-substituted phenolic motif can influence acidity, lipophilicity, and membrane partitioning, which are parameters of interest in medicinal chemistry design; however, no pharmacological activity is asserted here.
If biological assays are contemplated, ensure appropriate containment and waste handling pursuant to institutional EHS policies and consult the SDS for exposure limits and acute toxicity information if available.
Buffer Applications
Not typically used as a buffering agent. As a hydrophobic phenolic building block, it does not form defined buffer systems in the biological pH range.
Practical note: If present in aqueous systems (e.g., environmental partitioning studies), pH control should be achieved with standard buffers (phosphate, HEPES, acetate). The phenolic pKa of related compounds lies near neutral-to-basic pH, but this compound is not recommended as a buffer component.
For laboratory work with this reagent, refer instead to the sections on Reaction & Applications and Synthetic Utility.
Green Alternatives
While the compound itself is a building block, greener choices can be made in the solvents, reagents, and catalysts employed with it.
Greener solvent options (literature guidance):
Replace chlorinated solvents (e.g., DCM) with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
For polar aprotic needs, consider propylene carbonate or dimethyl carbonate as partial substitutes for DMF/DMSO/MeCN when compatible with the reaction.
Base and reagent selection:
Favor inorganic carbonates (K2CO3, K3PO4) over strong, hazardous bases where possible.
Use carbonate activation (e.g., organic carbonates) or enzymatic acylations as alternatives to acid chlorides for esterification when appropriate.
Catalysis improvements:
Employ highly active Pd catalysts/ligands that operate at lower loadings and temperatures to reduce energy and metal usage; explore Ni-catalyzed couplings for aryl chlorides as a lower-Pd alternative.
Aqueous micellar catalysis (TPGS-750-M or similar) can enable cross-coupling in water or minimal organic cosolvent, reducing solvent footprint.
Comparative considerations:
DCM vs. EtOAc: EtOAc offers lower toxicity and better environmental profile but may require temperature control due to lower boiling point.
THF vs. 2-MeTHF: 2-MeTHF is biorenewable and forms fewer peroxides; solubility and rate can be similar, though 2-MeTHF is less polar.
Implement green metrics (E-factor, PMI) tracking for campaigns involving this intermediate to quantify improvements.
Pharmaceutical Uses
No therapeutic or clinical claims are made for this item. It is supplied for research and laboratory use only.
Formulation/excipient status: Not typically used as a pharmaceutical excipient. Phenolic, halogenated aromatics are generally avoided as inactive ingredients due to irritancy and reactivity.
Process chemistry relevance (general): As a building block, 2-chloro-6-methylphenol may appear in synthetic routes to APIs or intermediates where an ortho-halophenol motif is required. In such cases, process-grade specifications, impurity control, and residual solvent/metal limits must be established per internal quality systems; these are not specified for this catalog item.
For any GMP or clinical manufacturing context, source material specifications, change control, and regulatory filings must be addressed independently; this SKU is designated for research use only per Product Data.
Physical Properties
Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for 2-chloro-6-methylphenol (for reference only; not item specifications):
Physical state/appearance: Typically a crystalline solid or low-melting solid/liquid depending on purity and temperature (phenolic halocresols often have moderate melting points). Exact appearance for this SKU is not specified.
Acidity: Phenolic pKa typically in the ~9–10 range; ortho-chloro substitution can slightly increase acidity (literature trend for halophenols), placing expected pKa modestly below unsubstituted cresols.
Polarity/partitioning: Moderately hydrophobic aromatic core with a polar OH; expected to exhibit low water solubility and good solubility in common organic solvents (ethers, esters, chlorinated solvents, aromatics, alcohols) per general behavior of halogenated cresols.
Hydrogen bonding: Capable of intramolecular H-bonding (o-substituted phenols) which can influence melting point and volatility relative to para/meta isomers.
Volatility: Lower volatility than non-hydrogen-bonding aromatics of similar MW due to phenolic association; heated handling should use appropriate ventilation.
Note: Specific numeric values (bp, mp, density, refractive index, solubility, logP) are not provided for this catalog item. Consult the CoA/Spec Sheet or SDS for verified numbers if required for process design.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general information for professional selection):
Analytical/Reagent grade: Typically specifies tight limits on non-volatile residue, trace metals, and well-defined purity suitable for analytical work.
Synthesis grade/Technical grade: Suited for routine synthetic transformations; may have broader impurity profiles but generally acceptable for many organic reactions.
HPLC/UV grade (for solvents): Emphasizes low UV-absorbing impurities and particulates; typically not applicable to solid building blocks like this compound.
Considerations for this compound type (halogenated phenol):
Trace metal content can impact Pd-catalyzed cross-couplings at the aryl chloride; for sensitive catalysis, verify trace metals (if specification is available) or employ catalyst pre-treatment/filtration.
Peroxide content is not typically relevant to phenolic solids but residual acidic/neutral impurities (e.g., phenolic isomers) may influence reactivity or odor; assess by GC or HPLC if process-critical.
Water content can affect base-mediated O-alkylation/acylation equilibria; Karl Fischer data, if available on the CoA, is helpful for reproducibility.
For this SKU, consult the CoA/Spec Sheet for actual assay, impurity profile, and any stabilizer information (none stated in Product Data).
Reaction and Applications
2-Chloro-6-methylphenol is a bifunctional aryl building block combining a phenolic OH and an aryl chloride handle, enabling orthogonal transformations.
Functional diversification via the phenolic OH:
Ether formation: Williamson ether synthesis under basic conditions (e.g., K2CO3/DMF with alkyl halides). Mitsunobu etherification is also possible for difficult alkyl partners.
Ester/carbonate/urethane formation: Using acyl chlorides/anhydrides (DMAP catalysis), carbonyl diimidazole (CDI), or chloroformates to access carbonates; reaction conditions tune leaving group ability for subsequent cross-couplings.
Protective groups: Formation of benzyl or silyl (TBDMS, TIPS) ethers to mask phenolic acidity during metal-catalyzed coupling at C–Cl.
Cross-coupling at the aryl chloride (literature precedents):
Suzuki–Miyaura: Coupling with aryl/alkenyl boron reagents using Pd(0/II) catalysts and bulky electron-rich ligands (e.g., SPhos, XPhos) to activate aryl chlorides; bases such as K3PO4 or Cs2CO3 in toluene/dioxane/H2O.
Buchwald–Hartwig amination: Formation of aryl amines with primary/secondary amines; BrettPhos/XantPhos-type ligands often effective for aryl chlorides.
Sonogashira: Coupling with terminal alkynes (Pd/Cu co-catalysis) to introduce ethynyl units; protect phenol if necessary.
Borylation (Miyaura–Ishiyama): Conversion to the corresponding aryl boronate ester (e.g., with B2pin2) as a versatile intermediate.
Electrophilic aromatic substitution (EAS): The phenolic OH strongly directs ortho/para substitution; the existing ortho substituents (Cl, Me) bias further substitution to the para position relative to OH.
Applications:
Useful intermediate for agrochemical and materials targets where halogenated cresol motifs are required.
Scaffold for ligand development and polymer precursors via ether/ester linkages.
Always adjust protecting group strategy to maintain selectivity between O-functionalization and C–Cl activation.
Reaction Conditions
General literature guidance for transforming 2-chloro-6-methylphenol (not item-specific specifications):
O-alkylation (Williamson ether synthesis):
Base: K2CO3 or Cs2CO3 (1.5–2.0 equiv) in DMF, MeCN, or acetone.
Electrophile: Primary alkyl halide or sulfate (1.1–1.5 equiv).
Temp/time: 25–60°C, 2–16 h. Monitor by TLC/LC-MS. Minimize water content.
O-acylation (ester/carbonate):
Reagents: Acyl chloride/anhydride (1.1–1.5 equiv) with Et3N or pyridine; catalytic DMAP (5–10 mol%).
Solvent: DCM or toluene.
Temp: 0–25°C for exotherm control; 1–4 h typical.
Suzuki–Miyaura coupling at C–Cl:
Catalyst/ligand: Pd2(dba)3 (1–2 mol% Pd) with SPhos or XPhos (2–4 mol%) or precatalysts (e.g., Pd-PEPPSI). For Ni, NiCl2(dppp) (5–10 mol%) can be considered.
Base: K3PO4, Cs2CO3, or Na2CO3 (2–3 equiv).
Solvent: Toluene, 1,4-dioxane, or THF with 5–20% H2O.
Temp/time: 70–110°C, 4–18 h. Protect or neutralize phenol to reduce catalyst inhibition.
Buchwald–Hartwig amination:
Catalyst/ligand: Pd(OAc)2 (1–3 mol%) with BrettPhos or RuPhos (2–6 mol%).
Base: NaOtBu or Cs2CO3 (2–3 equiv).
Solvent: Toluene or dioxane.
Temp: 80–110°C.
Sonogashira coupling:
Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%), Et3N or iPr2NH as base, THF or toluene, 25–80°C.
Expected yields are substrate- and condition-dependent; verify on small scale. Phenolic OH may require protection or in situ base to avoid catalyst deactivation.
Safety and Handling
Item-specific hazard fields (GHS, H-statements, pictograms) are not provided in the Product Data. Always consult the SDS for authoritative classification and first-aid instructions.
General safety profile for halogenated phenols (literature/analogous compounds):
Likely hazards: Skin and eye irritation or burns (phenols are corrosive/irritant), respiratory irritation if vapors/aerosols are generated, and toxicity if ingested or absorbed through skin. Aryl chlorides may add irritation potential.
PPE: Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. Handle in a fume hood to minimize inhalation exposure. Avoid skin contact; phenols can be absorbed dermally.
Handling: Prevent contact with strong oxidizers and strong bases/acids that can lead to exothermic neutralization or oxidation. Keep containers tightly closed to limit moisture and air exposure (phenols can slowly oxidize/discolor on air/light exposure).
First aid (summary; defer to SDS):
Skin: Immediate decontamination with copious water and soap; remove contaminated clothing.
Eyes: Rinse cautiously with water for at least 15 minutes; seek medical attention.
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Combustible organic. Use CO2, dry chemical, or foam. Phenolic compounds may produce irritating or toxic fumes (HCl, CO/CO2) on thermal decomposition.
Storage per Product Data: Room temperature; keep container closed. As good practice, store in a cool, dry, well-ventilated area away from incompatible reagents and direct light.
Solvent Selection
This product is a small, moderately hydrophobic aromatic phenol; solvent choice depends on the transformation (as reagent/building block) rather than its use as a solvent.
Polarity/miscibility (general behavior):
Low water solubility; miscible or highly soluble in organic solvents such as dichloromethane (DCM), ethyl acetate, toluene, THF, acetone, and alcohols (literature trend for halogenated cresols).
Phenolic OH can engage in hydrogen bonding; protic solvents (MeOH, EtOH) may shift equilibria in O-alkylation/acylation.
Typical solvent choices by application:
O-alkylation/acylation of phenol: Polar aprotic solvents (DMF, DMSO, MeCN, acetone) with a suitable base (K2CO3, Cs2CO3, NaH). For acylations, DCM or toluene with acid chlorides/anhydrides and base (pyridine, triethylamine).
Pd-catalyzed cross-coupling at C–Cl: Toluene, dioxane, THF, or tert-amyl alcohol with bases like K3PO4, Cs2CO3. Aqueous-organic biphasic systems (toluene/H2O) can be effective with phase-transfer.
Protection as silyl/benzyl ether: DCM, THF, or DMF.
Selection tips:
If intramolecular H-bonding hinders reactivity, choose more polar solvents and/or add a soluble base to disrupt association.
For chromatographic purification, use hexanes/EtOAc or toluene/EtOAc gradients; aromatic character aids in normal-phase separations.
Note: No item-specific solubility specs are provided for this SKU; validate solvent choices on small scale.
Storage and Reconstitution
Item-specific storage: Room temperature (per Product Data). Shipped under normal conditions.
General handling for phenolic building blocks:
Store tightly closed in a cool, dry, well-ventilated area. Protect from moisture, air, and light to minimize slow oxidation/discoloration typical of phenols.
If long-term storage is anticipated, consider using amber containers and minimizing headspace exposure; optional inert gas blanket can help preserve quality (general best practice; not a requirement of this SKU).
Reconstitution/solubilization:
Not applicable as a biological reagent. For solution preparation in synthesis or analysis, dissolve in a compatible organic solvent (e.g., DCM, EtOAc, toluene, THF, MeOH/EtOH) at desired concentration. Filter if particulate is present.
For quantitative NMR or HPLC sample prep, use deuterated solvents (e.g., CDCl3, DMSO-d6) or HPLC-grade solvents; exact solvent choice depends on the method.
Stability notes:
Avoid prolonged exposure to strong bases or oxidants during storage. Trace acids/bases can catalyze side reactions; use clean, dry glassware.
Refer to the product’s CoA/Spec Sheet and SDS for any item-specific stability data and detailed handling guidance.
Structure and Identity
A halogenated cresol (o-substituted phenol) featuring an ortho-chloro and an ortho-methyl group flanking the phenolic hydroxyl.
Item-specific identifiers (from Product Data):
SKU: C134880
Product name: 2-Chloro-6-methylphenol
CAS: 87-64-9
CID: 6898
InChIKey: 443550 (as provided)
Storage: Room temperature; shipped under normal conditions
Literature/computed identity details (general reference data; not item-specific specifications):
2D structure in words: A benzene ring with an OH at position 1; immediately adjacent on one side (position 2) is chlorine; adjacent on the other side (position 6) is a methyl group. No stereocenters; planar aromatic system.
Resonance/inductive effects: Phenolic oxygen donates electron density into the ring (activating/ortho–para directing), while the chloro substituent is inductively withdrawing but resonance donating; the net directs electrophilic substitution to the remaining ortho/para sites relative to OH.
Synthetic Utility
Key reactivity stems from the orthogonal handles:
Phenolic OH (nucleophile/weak acid):
Alkylation to aryl ethers (Williamson) offers modular diversification; benzyl ethers enable later deprotection (hydrogenolysis) after C–Cl couplings.
Acylation to esters/carbonates provides leaving groups convertible to phenoxides in subsequent steps or serves as masked phenols.
Silylation (TBDMS/TIPS) protects the OH during metal-catalyzed couplings, reducing catalyst poisoning.
Aryl chloride (electrophile in cross-coupling):
Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings introduce aryl, amine, and alkyne moieties respectively. Use ligands tailored for aryl chlorides (e.g., BrettPhos, SPhos) and consider base/solvent combinations that tolerate phenols or their protected variants.
Direct borylation (e.g., Pd or Ni catalysis with B2pin2) creates a boronate for further C–C bond construction.
Alternatively, derivatize the phenol to a sulfonate (e.g., tosylate) as an aryl electrophile in certain cross-couplings or SNAr-like reactions (with appropriately activated partners).
Regioselectivity/EAS planning:
With ortho positions occupied, electrophilic substitution typically targets the para site relative to OH, enabling selective nitration, halogenation, or Friedel–Crafts under controlled conditions (protecting OH often required).
This dual-function scaffold is valuable for step-efficient assembly of densely substituted aromatics.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting reagent (e.g., antibody, ligand with defined biomolecular target profile). No antigen, epitope, clone, isotype, or species reactivity applies.
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