This compound belongs to the class of organic compounds known as m-chlorophenols. These are chlorophenols carrying a iodine at the C3 position of the 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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
156.610 g/mol
XLogP3
3.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
1
Exact Mass
156.034 Da
Monoisotopic Mass
156.034 Da
Topological Polar Surface Area
20.200 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
105.000
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic uses, refer to the Reaction Conditions and Synthetic Utility sections for literature-style procedures and optimization guidance.
Biological Roles
Item-specific (from Product Data)
Category: 生命科学 (Life Sciences); For research use only.
Literature/general
No specific endogenous biological role is described for 3-chloro-4-ethylphenol. It is a synthetic, halogenated phenolic derivative used as a chemical intermediate.
Phenolic motifs broadly participate in hydrogen-bonding and redox chemistry in biomolecular contexts; however, halogenated, para-alkyl phenols like this are typically employed as small-molecule fragments or reference standards in analytical or environmental studies rather than as biological co-factors.
Caution: phenolic compounds can interact nonspecifically with proteins and membranes due to amphiphilicity; any bioassay use should include appropriate controls to detect assay interference (e.g., redox cycling, fluorescence quenching). No claims are made for biological activity of this product.
Buffer Applications
This compound is not a buffering reagent. As a hydrophobic, weakly acidic phenol, it is not typically used to prepare biological or analytical buffer systems.
Practical note: If present in buffered media during assays, pH above the phenolic pKa will increase ionization (phenolate formation), affecting solubility and partitioning. Choose organic cosolvents or surfactants appropriately and validate assay controls.
Green Alternatives
Design considerations
Aryl chlorides are attractive from cost and availability but can require stronger catalytic systems versus aryl bromides/iodides. Choosing ligands/solvents that reduce energy input and catalyst loading improves greenness.
Greener choices around this substrate (literature-based; balance benefits/tradeoffs)
Solvents for cross-coupling and O-alkylation
Prefer 2-MeTHF, CPME, or toluene over DMF/DMAc when feasible to reduce reproductive toxicity concerns and ease solvent recovery.
Ethyl acetate or propylene carbonate can replace chlorinated solvents (DCM) for acylations with appropriate bases and temperatures.
Coupling electrophile alternatives
If aryl chloride activation is challenging, consider generating an aryl boronate (via borylation) and using it in convergent couplings, or prepare a sulfonate (aryl triflate) from the phenol to enable milder cross-couplings. Tradeoff: triflates are moisture-sensitive and less atom-economical.
Bases and workup
Use inorganic bases (K2CO3) or carbonate buffers under phase-transfer rather than NaH to reduce hazard and improve scalability.
Energy and catalyst loadings
Modern Pd(0)–biaryl phosphine systems (e.g., XPhos-type) enable room-temperature to mild couplings, reducing heating demand; nickel catalysis may offer earth-abundant alternatives for some transformations.
Comparison snapshot (general)
2-MeTHF vs THF: lower peroxide formation tendency, biorenewable feedstock, higher bp (82–85 °C) enabling higher-temperature couplings; slightly lower polarity can affect solubility.
CPME vs DCM: reduced toxicity and persistence; higher bp requires different evaporation strategy; less dense than water simplifies separations.
Pharmaceutical Uses
Item-specific (from Product Data)
No pharmacopeial or excipient status specified. For research use only.
Literature/general (formulation and process chemistry context; no clinical claims)
Role: synthetic intermediate or fragment in medicinal chemistry campaigns where a phenolic handle and an aryl chloride are leveraged for rapid analog generation (e.g., O-alkyl/aryl diversification and Pd-catalyzed coupling at C–Cl).
Considerations for process development: isomer control, residual halogen and phenolic impurities, and potential for oxidative discoloration. Salt formation is generally not applicable; protect the phenol or cap as needed to meet stability targets.
Regulatory note: halogenated phenols may have specific impurity assessment requirements; ensure route scouting and impurity fate studies early in scale-up.
Physical Properties
Item-specific (from 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.
Density, melting point, boiling point, refractive index, UV cutoff, water content, residual metals: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general (typical for substituted phenols; not item specifications)
Physical state: typically a low–melting solid or high-boiling liquid for mono-alkyl/halo phenols of this ring substitution class.
Acidity: weakly acidic phenol; pKa commonly near 10 for phenols. Electron withdrawal by Cl lowers pKa slightly; ethyl raises it slightly; net expected near phenol values (literature trend).
Solubility profile: sparingly soluble in water; soluble in common organic solvents (EtOAc, THF, MeOH, acetone, DCM, toluene). Phenolic OH enables H-bonding and enhanced solubility in polar organics.
Partitioning: phenolic derivatives with one halogen and one ethyl group generally exhibit moderate hydrophobicity (logP typically >2, literature trend).
Practical implications
Expect limited aqueous solubility; consider cosolvents or base to form the phenolate for aqueous workups/extractions.
Phenolic OH can engage in intramolecular H-bonding with bases; drying over molecular sieves or by azeotropy is typically effective prior to moisture-sensitive reactions.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general)
Research grade materials typically balance assay purity with cost; trace impurity limits (metals, halides, water, residual solvents) vary by supplier and batch.
For cross-coupling or organometallic applications, low halide/metal background and low water are advantageous; review CoA for assay purity, GC/HPLC area %, and residual solvent profile.
For spectroscopy or kinetics, consider lots with low UV-absorbing impurities (HPLC/UV grade if available) to minimize baseline drift.
Practical QC considerations for phenolic building blocks
Isomeric purity: verify positional isomer content by 1H/13C NMR (diagnostic para-ethyl pattern), and GC/MS.
Residual inorganic halides: can elevate background in catalytic reactions; check IC if sensitivity demands.
Water content: phenols may hydrogen-bond to water; Karl Fischer values influence O-alkylation stoichiometry. If not specified, determine in-house before moisture-sensitive use.
Reaction and Applications
3-Chloro-4-ethylphenol is a bifunctional aryl building block combining a nucleophilic phenol and an electrophilic aryl chloride, enabling orthogonal transformations.
O‑Functionalization (nucleophilic at O)
O-alkylation and O-arylation: formation of aryl ethers using base (K2CO3, Cs2CO3) or catalytic systems (CuI with diamine ligands; Pd/Buchwald-type ligands). Protecting-group strategies (silyl, benzyl, carbonate) can be applied to control chemoselectivity.
O-acylation: acyl chlorides/anhydrides in DCM/THF with Et3N, DMAP catalysis for esters and carbonates. Useful for pro-moiety installation or polymer precursors.
C–X and C–C bond formation (electrophilic at aryl chloride)
Cross-coupling at C–Cl: Suzuki–Miyaura (B(OH)2), Buchwald–Hartwig amination (amines), Negishi/Kumada (organozinc/magnesium), with Pd catalysts and electron-rich bulky ligands (e.g., XPhos, SPhos, BrettPhos) to activate the aryl chloride. The para-ethyl and meta-OH directing effects influence regioselectivity in further substitution.
Metal–halogen exchange: directed ortho-metalation adjacent to phenol (after protection) or lithium–halogen exchange can enable formylation, borylation, or electrophile quench.
Electrophilic aromatic substitution (on the ring)
After masking/derivatizing the OH, Friedel–Crafts or nitration/sulfonation can proceed with predictable directing effects (OH activates ortho/para; Cl is ortho/para-directing but deactivating). Control via protecting groups is recommended to avoid O-acylation/alkylation.
Applications
Fragment for ligand and materials synthesis (phenoxy polymers, aryl ether frameworks).
Intermediate toward substituted anisoles/aryl ethers, carbamates, and ureas after O-functionalization.
Handle the two handles sequentially: commonly protect OH, couple at C–Cl, then unveil/react at O.
Note: Reaction families and strategies above are general literature guidance for this substitution pattern; optimize conditions per substrate.
Reaction Conditions
General literature guidance for this substitution pattern (optimize per substrate; not item-specific specifications):
O-Alkylation (Williamson ether synthesis)
Typical: 1.0 equiv substrate, 1.2–2.0 equiv alkyl halide, 1.5–2.5 equiv K2CO3 or Cs2CO3 in acetone, acetonitrile, or DMF; 25–60 °C, 2–16 h. For secondary halides, use stronger base (NaH) in THF at 0–25 °C with careful addition.
O-Arylation (Buchwald–Hartwig or Ullmann-type)
Pd2(dba)3 (1–2 mol %) with XPhos/SPhos (2–4 mol %) or CuI (5–10 mol %) with diamine ligands; base K3PO4/Cs2CO3; solvent toluene, dioxane, or 2-MeTHF; 60–110 °C, 4–24 h.
Suzuki–Miyaura coupling at aryl chloride
Pd(PPh3)4 or Pd-precatalyst (0.5–2 mol %) with bulky electron-rich ligand (e.g., XPhos), base K3PO4 or K2CO3, solvent 1,4-dioxane/H2O or toluene/EtOH/H2O; 60–100 °C, 2–16 h. Aryl boronic acid/ester 1.2–1.5 equiv.
Buchwald–Hartwig amination
Pd2(dba)3 (1 mol %) + BrettPhos or RuPhos, NaOtBu or Cs2CO3, toluene or dioxane; 80–110 °C. Primary/secondary amines 1.2–1.5 equiv.
Alkyl protection: MeI/Na2CO3 (methyl ether); hydrogenolysis for benzyl ethers (BnBr + base; Pd/C, H2 for deprotection).
Workup tips
Neutralize bases before extraction; phenol/phenolate partitioning depends on pH—acidify to pH ~5–6 to recover neutral phenol into organic phase.
Avoid strong acids with silyl-protected intermediates to prevent premature deprotection.
Safety and Handling
Item-specific (from Product Data)
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
Storage conditions: Room temperature.
General safety guidance (literature-based; consult SDS for definitive instructions)
Likely hazards: phenolic compounds can be irritating/corrosive to skin and eyes; chlorinated phenols may be harmful if inhaled or ingested; avoid aerosol generation.
PPE: lab coat, nitrile gloves (change regularly), safety goggles/face shield. Handle in fume hood to minimize vapor and aerosol exposure.
Incompatibilities: strong oxidizers (risk of exotherm), strong bases (forms phenolate; may increase skin penetration), acid chlorides/anhydrides (acylation) without control, reactive metals.
First aid (overview):
Skin: immediate decontamination with copious water and soap; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention.
Inhalation: move to fresh air; monitor respiration; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: combustible organic; use CO2, dry chemical, or foam. Combustion may produce HCl and corrosive fumes—firefighters should use SCBA.
Always refer to the current Aladdin Scientific SDS for authoritative hazard and response information for this specific item.
Solvent Selection
Although 3-chloro-4-ethylphenol is a reagent rather than a solvent, choosing compatible media is critical for its use.
Preferred media: polar aprotic solvents (DMF, DMAc, DMSO, MeCN) for O-alkylation/acylation; ethers (THF, 2-MeTHF) and esters (EtOAc) for neutral transformations; chlorinated solvents (DCM) for extra solubility, if appropriate.
Alcohols (MeOH, EtOH): useful for recrystallization or as cosolvents; note potential for transesterification or ether formation under basic conditions.
Aqueous handling
Water solubility is limited; solubility increases upon deprotonation to the phenolate. Liquid–liquid extraction favors organic phase unless a strong base is present.
Selection guidelines by operation
O-Alkylation: DMF or acetone with K2CO3/Cs2CO3; phase-transfer conditions (toluene/aqueous base) also effective.
O-Acylation: DCM or THF with acyl chloride/anhydride and a non-nucleophilic base (Et3N, DIPEA, pyridine).
Cross-coupling at aryl chloride: toluene, dioxane, or CPME with polar cosolvent (t-BuOH, DMAc) as needed; choose solvent compatible with the ligand system.
Small comparison (general)
DMF vs DMSO: DMF eases workup (washable), DMSO offers higher polarity but is harder to remove.
THF vs 2-MeTHF: 2-MeTHF offers greener profile and higher boiling point, aiding coupling chemistry while improving safety.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (literature-based; not item-specific specifications)
Keep container tightly closed in a dry, well-ventilated place. Protect from moisture; consider storing under inert gas for long-term stability of sensitive phenolic compounds.
Avoid prolonged exposure to light and air to minimize potential oxidative discoloration typical of phenols.
If solid, break up clumps under inert atmosphere if caking occurs; if liquid, store in amber glass with PTFE-lined cap.
Reconstitution/handling
Readily dissolves in common organic solvents (e.g., DCM, THF, EtOAc, MeOH, DMF). Prepare stock solutions fresh when possible; for longer storage, use dry, oxygen-free solvents and inert atmosphere.
Before moisture-sensitive reactions, dry by azeotrope with toluene or co-evaporate with dry acetonitrile; or briefly expose to activated 3 Å molecular sieves.
Always consult the product CoA and SDS for lot-specific stability and handling recommendations.
Structure and Identity
Brief overview: 3-Chloro-4-ethylphenol is a chlorinated, para-ethyl-substituted phenolic building block useful for O-functionalization and cross-coupling chemistry on an aryl chloride scaffold.
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 (general reference; not item specifications)
Putative molecular formula (structure-based): C8H9ClO
Approx. formula weight (calculated): ~156.61 g/mol
Structural features: phenolic OH at C1; chloro substituent meta to OH (C3); ethyl substituent para to OH (C4); planar aromatic ring; one hydrogen-bond donor (phenolic OH) and one acceptor (phenolic O); one aryl chloride leaving group.
2D description: a benzene ring bearing OH at one carbon, an ethyl group directly across the ring (para), and a chlorine adjacent to the para site (meta to OH).
Aryl chloride (electrophilic site): participates in Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira after halogen–metal exchange or direct activation), enabling introduction of aryl, vinyl, alkynyl, or amine substituents.
Directing effects and regiocontrol
The phenolic OH (or its protected form) activates ortho/para positions toward EAS; the chloro substituent is deactivating but ortho/para-directing. Strategic protection (e.g., O-methyl/O-silyl) helps channel reactions to the ring versus the oxygen.
Retrosynthetic flexibility
Can serve as either the nucleophile (via phenolate) or the electrophile (via C–Cl), enabling convergent two-step sequences: protect OH → cross-couple at C–Cl → deprotect → O-functionalize.
Derivatization pathways
Borylation (Miyaaura–Ishiyama) of the aryl chloride followed by Suzuki coupling; or direct Suzuki on the aryl chloride with suitable ligation.
Nucleophilic aromatic substitution is generally unfavorable on simple aryl chlorides lacking strong ortho/para electron-withdrawing groups; employ transition-metal catalysis instead.
These features support rapid library synthesis, materials functionalization, and access to phenoxy scaffolds.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope or species reactivity information applies.
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