2-Chloro-4-(2-hydroxyethyl)phenol - ≥95% , CAS No.50972-63-9

CAS: 50972-63-9 Cat. No.: C1036424 Formula: C₈H₉ClO₂ Peso molecolare: 172.610 Numero EC: 821-189-3

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: C1=CC(=C(C=C1CCO)Cl)O
• IUPAC Name: 2-chloro-4-(2-hydroxyethyl)phenol
• InChIKey: ZGAMFWSQAUCSGB-UHFFFAOYSA-N
• INCHI: 1S/C8H9ClO2/c9-7-5-6(3-4-10)1-2-8(7)11/h1-2,5,10-11H,3-4H2
• Peso molecolare: 172.610

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenols
      • Subclass Tyrosols and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenols
• Subclass: Tyrosols and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Tyrosols
• Alternative Parents: O-chlorophenols Chlorobenzenes 1-hydroxy-2-unsubstituted benzenoids Aryl chlorides Primary alcohols Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Tyrosol - 2-halophenol - 2-chlorophenol - 1-hydroxy-2-unsubstituted benzenoid - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Primary alcohol - Hydrocarbon derivative - Organic oxygen compound - Alcohol - Organooxygen compound - Organohalogen compound - Organochloride - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as tyrosols. These are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 172.610 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 172.029 Da
• Monoisotopic Mass: 172.029 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 119.000
• 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

Application Protocols

No application protocols are specified for this item in the Product Data. As a small-molecule building block, typical “assay protocols” do not apply. For synthetic usage, refer to the Reaction Conditions and Synthetic Utility sections for general guidance.

Research Use Note

• For research use only. Not for human or veterinary use.

Biological Roles

No inherent biological role is assigned to 2-chloro-4-(2-hydroxyethyl)phenol; it is a synthetic small molecule used as a building block.

General biochemical context (literature/general)

• Phenolic groups can engage in hydrogen bonding and π–π interactions with proteins and nucleic acids; the additional primary alcohol increases polarity and can modulate membrane permeability in analog design.
• Aryl chlorides are common synthetic handles; in biological settings, the C–Cl bond on an aromatic ring is typically metabolically stable but may undergo oxidative metabolism after other modifications.
• Phenolic functionalities are often subject to phase II metabolism (glucuronidation/sulfation) in vivo; the presence of two hydroxyl groups could increase conjugation potential in theoretical pharmacokinetic studies.

Note: Any discussion of metabolism/biological interaction is provided as general chemical biology context. This product is supplied strictly for research use only and is not intended for diagnostic, therapeutic, or any clinical use.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare defined buffer systems. Its phenolic OH (weak acid) does not provide a practical, narrow pH buffering range at typical laboratory concentrations.

Practical note

• If dissolved in buffered media for assays, be aware that phenols can interact with proteins and plastics; include appropriate controls. Adjust pH with standard buffers (phosphate, HEPES, TRIS) rather than relying on this compound for pH control.

Green Alternatives

While this entry is a discrete building block rather than a solvent or reagent class, greener choices pertain to the processes using it.

• Greener solvents for processing (literature/general)

  • Favor EtOAc, IPA, MeOH, or 2‑MeTHF over chlorinated solvents when feasible. For cross‑couplings, alcoholic solvents or aqueous micellar media (e.g., TPGS‑750‑M) can reduce organic solvent usage.
  • For extractions, MTBE or CPME can substitute for DCM where partitioning allows.

• Greener oxidation/reduction

  • Oxidize the side‑chain alcohol using TEMPO/bleach (NaOCl, aqueous biphasic) or O2/NOx catalysts in place of chromium(VI) reagents. For aldehyde formation, Dess–Martin or catalytic TEMPO/NaClO2 alternatives minimize heavy-metal waste compared to Swern/Cr(VI).

• Catalysis choices

  • Employ modern ligand systems that enable Ar–Cl activation at lower catalyst loadings (e.g., biaryl phosphines, Pd‑NHC) and explore nickel catalysis for reduced precious-metal footprint.

• Energy and protection economy

  • Consider telescoping steps (e.g., in situ protection–coupling–deprotection) and room‑temperature couplings under aqueous conditions. Evaluate carbonate or carbonate‑free protecting strategies to cut auxiliary waste.

Comparison snapshot (general)

• Using 2‑MeTHF or CPME vs DCM: lower toxicity, renewable origin (2‑MeTHF), but higher boiling points; may lengthen concentration times. Aqueous micellar media reduce solvent volumes but may require surfactant removal downstream.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided in the Product Data for this item.

Context (general, non-clinical)

• As a bifunctional aromatic intermediate, 2-chloro-4-(2-hydroxyethyl)phenol could serve in medicinal chemistry and process development as a starting material for more complex molecules via O‑derivatization and cross‑coupling. Any such use remains strictly in preclinical research and development settings.

Note: This product is for research use only and is not intended for human or veterinary use, formulation, or clinical applications.

Physical Properties

Item-specific specifications (for this catalog item)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed properties (for reference only; not product specifications)

• Molecular formula: C8H9ClO2 (computed from name/structure)
• Molecular weight: ~172.61 g/mol (computed)
• Acid–base character: contains a phenolic OH (weak acid) and a primary aliphatic alcohol (very weak acid/neutral). Phenolic pKa values typically ~9–10 in water (literature, unsubstituted phenol ~9.9); ortho-chloro substitution can modestly increase acidity; exact pKa for this compound not found in standard references.
• Polarity/solubility (qualitative, literature/general): amphipathic; expected to be soluble in polar organic solvents (e.g., alcohols, acetone, acetonitrile, DMF, DMSO) and sparingly to moderately soluble in water due to the presence of two OH groups balanced by an aromatic ring and aryl chloride.
• Partitioning (qualitative): aryl chloride plus phenyl ring confer hydrophobicity; two OH groups increase hydrogen-bonding capacity; overall moderate polarity.

Not available in the Product Data (do not treat the following as specifications)

• Melting point, boiling point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet and SDS.

Quality and Grades

• Grade/Purity for this specific item: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on grades (for context)

• Research-grade organic intermediates are typically supplied at ≥95% purity unless otherwise stated, sufficient for most synthetic and screening workflows. If trace metals, water, or UV cutoffs matter (e.g., for catalysis or photochemical studies), request the detailed specification/CoA.
• Stabilizers: None listed in the Product Data. If ultra-low peroxide, metal, or water content are required for your application (e.g., sensitive cross-couplings or moisture-intolerant steps), confirm via CoA or pre-dry/purify prior to use.
• Lot-specific documentation: For NMR purity, residual solvents, and Karl Fischer water content (if measured), consult the lot CoA. If you require particular analytical criteria (GC/HPLC area %, qNMR, chiral purity if applicable), specify at time of order.

Fit-for-purpose considerations

• Phenolic content can influence assay backgrounds (UV absorbance ~270–290 nm region for many phenolics; exact spectrum item-specific). For chromatographic detection or photochemical work, consider HPLC/UV screening on receipt.
• If the compound will be used as a coupling partner in Pd-catalyzed reactions, trace metal content in the reagent is usually not critical; however, dryness and absence of inhibitors can be important for downstream transformations.

Reaction and Applications

Use this reagent as a multifunctional aromatic synthon combining: (i) a phenolic OH (nucleophile/acid), (ii) a benzylic primary alcohol (oxidation/derivatization handle), and (iii) an aryl chloride (cross-coupling/activation site).

Representative application families (literature/general)

• Protective group chemistry: Selective protection of either the phenolic OH (e.g., as silyl ether, benzyl ether, carbonate) or the primary alcohol (e.g., as TBDMS/TBDPS ether) enables orthogonal manipulations. Phenolic protection can be crucial to avoid undesired O‑acylation/alkylation.
• O‑functionalization: Phenolic O‑alkylation/acylation to access aryl ethers and aryl esters; Mitsunobu conditions can invert a chiral coupling partner onto the phenol. Benzylic alcohol can be esterified, carbamoylated, or converted to halides (e.g., via Appel) for further elaboration.
• Oxidation/reduction: Side‑chain primary alcohol oxidation (e.g., TEMPO/bleach, Dess–Martin, Swern) to aldehyde or acid (Pinnick), enabling homologation or cyclization strategies.
• Cross‑coupling via Ar–Cl: Pd‑catalyzed Suzuki–Miyaura, Buchwald–Hartwig (after phenol protection or as Ar–OTf if phenol pre-activated), Sonogashira, and Negishi couplings are feasible; Ar–Cl typically requires optimized ligands (e.g., dialkylbiaryl phosphines) and bases.
• Nucleophilic aromatic substitution (SNAr): The 2‑chloro group is weakly activated by the ortho phenol; activation increases upon conversion to an aryl triflate or under strong conditions if additional electron-withdrawing groups are introduced.
• Cyclization chemistry: Intramolecular etherification or acetal formation leveraging the side‑chain OH and phenol/activated ring can build benzofused motifs.

Use cases in discovery/route scouting (general)

• Scaffolding for bioisosteric analogs where a polar handle (–CH2CH2OH) is required.
• Intermediate toward chlorinated resorcinol/tyrosol analogs after selective transformations.

Reaction Conditions

General conditions reported for analogous substrates (guidance only; optimize per system)

• O‑Alkylation/acylation of the phenol

  • Base: K2CO3 or Cs2CO3 in acetone, acetonitrile, or DMF; or NaH in THF/DMF for stronger activation.
  • Electrophiles: alkyl halides/sulfates, acyl chlorides/anhydrides. Temperatures: 0–60 °C. Times: 1–16 h.

• Formation of aryl triflate from phenol

  • Reagents: Tf2O, pyridine/2,6‑lutidine or Et3N, DCM to CH2Cl2/DMF mixed; 0 °C to rt. Quench with aqueous base.

• Oxidation of the primary alcohol

  • Dess–Martin periodinane (DCM or EtOAc, rt, 0.5–3 h) to aldehyde.
  • TEMPO/NaOCl (biphasic H2O/CH2Cl2 or H2O/EtOAc, 0–5 °C to rt) for aldehyde; TEMPO/NaClO2 (Pinnick) to acid.

• Appel/halogenation of the primary alcohol

  • PPh3/CBr4 or PPh3/CCl4 in DCM (0 °C to rt, 1–4 h) to give benzylic halides suitable for SN2/coupling.

• Pd‑catalyzed cross‑coupling on Ar–Cl

  • Suzuki–Miyaura: Pd2(dba)3 or Pd(OAc)2 with SPhos/XPhos/RuPhos, base (K3PO4, K2CO3, or Cs2CO3), solvent (dioxane/H2O, toluene/H2O, or EtOH/H2O), 60–110 °C, 2–16 h.
  • Buchwald–Hartwig amination: Pd2(dba)3 or Pd(OAc)2 with BrettPhos/BippyPhos, base (NaOtBu, Cs2CO3), toluene/dioxane, 80–110 °C.
  • Sonogashira: Pd/Cu cocatalysis (e.g., PdCl2(PPh3)2, CuI), amine base (Et3N, iPr2NH), THF/amine or DMF, rt–80 °C.

• Selectivity considerations

  • Protect phenol when cross‑coupling to avoid competitive O‑arylation or catalyst inhibition. The aliphatic OH is less problematic but may be protected if required.

Note: These are literature-style general conditions for similar motifs and are not specifications for this product. Verify with small-scale trials.

Safety and Handling

Authoritative safety information for this catalog item is not provided in the Product Data. Always consult the SDS for this specific lot before use.

Item-specific hazard fields

• Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.

General safety considerations for chlorinated phenolic alcohols (literature/general guidance; not item-specific classification)

• Hazard profile: Phenolic compounds can be harmful by skin absorption and irritating to skin/eyes. Aryl chlorides and benzylic alcohols may cause irritation; phenols can be acutely toxic at sufficient dose. Avoid inhalation of dust/aerosols and contact with skin/eyes.
• PPE: Wear lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of vapors or dust.
• Incompatibilities: Strong oxidizers (risk of exotherm/oxidation), strong bases (can form phenolates; enhanced corrosivity), strong acids (possible dehydration of the side-chain alcohol under forcing conditions), acylating/alkylating agents (can react at OH groups). Avoid reactive metals if strong bases are present (formation of phenolates).
• Stability/other risks: Phenols may undergo slow air-oxidation or discoloration on prolonged exposure to air/light; benzylic alcohols can oxidize to aldehydes/acids under harsh conditions. This compound is not an ether; peroxide formation is not a specific concern.
• First aid (overview; defer to SDS): Eye/skin contact—rinse with water for at least 15 minutes and remove contaminated clothing; ingestion—rinse mouth, do not induce vomiting; inhalation—move to fresh air. Seek medical attention as appropriate.

Waste disposal

• Collect organics in halogenated organic waste if local rules classify aryl chlorides as halogenated; otherwise follow institutional procedures. Do not release to the environment.

Solvent Selection

This compound is an amphipathic aromatic bearing a phenolic OH and a primary alcohol, leading to good solubility in polar aprotic and protic organic solvents.

• Polarity class (general): moderate polarity aromatic polyol/aryl chloride.
• Likely solvent compatibility (general, not specifications)
  • Good: methanol, ethanol, isopropanol, acetone, acetonitrile, ethyl acetate, THF, DCM, DMF, DMSO.
  • Variable/limited: water (improved by mild basification to form the phenolate; verify experimentally), hexanes/heptane (limited due to hydrogen-bonding functionality).
• Practical tips
  • For aqueous workups, deprotonation (e.g., NaHCO3/Na2CO3) increases aqueous solubility; reprotonate on acidification to isolate the phenol.
  • For chromatographic purification, normal-phase silica with EtOAc/hexanes or DCM/MeOH gradients typically perform well; add 0.1–1% AcOH or Et3N to mitigate tailing from phenolic adsorption, as needed.
  • For NMR, CDCl3 often suffices; if solubility is limited or hydrogen bonding causes line broadening, use DMSO‑d6, acetone‑d6, or CD3OD.

Comparison to alternatives (general)

• Relative to more hydrophobic chlorophenols, the 2-hydroxyethyl group increases polarity and crystallization tendency; relative to diols without aryl chloride, this compound is less water-soluble but more GC‑amenable. Choose solvent system accordingly based on target operation (reaction vs. purification vs. analytics).

Storage and Reconstitution

• Storage (from Product Data): Store at room temperature.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.

General handling recommendations (literature/practice; not item-specific specs)

• Keep tightly closed in a dry environment. Phenolic compounds and benzylic alcohols may slowly oxidize or discolor on exposure to air/light; store in amber glass if possible and minimize headspace.
• If moisture sensitivity of your process is critical, store under inert gas and/or add desiccant in secondary containment.
• Before sensitive reactions, consider drying under high vacuum or by azeotrope (e.g., with toluene) to remove adventitious moisture.

Reconstitution/solubilization

• Soluble in many polar organic solvents (e.g., DMSO, DMF, MeOH, EtOH, acetone, EtOAc). Prepare stock solutions freshly or store aliquots at low temperature if long-term solution stability is required (solution stability not specified for this item; confirm experimentally).

Freeze–thaw guidance

• If storing as solution, aliquot to avoid repeated freeze–thaw. For solid material, allow to equilibrate to room temperature in closed container before opening to prevent moisture condensation.

Always consult the product’s SDS and lot-specific CoA for authoritative handling and storage instructions.

Structure and Identity

A chlorinated, dihydroxy-functional aromatic building block featuring a phenolic OH and a benzylic 2-hydroxyethyl side chain (para to the phenol) with a chloro substituent ortho to the phenolic OH.

• Item-specific identifiers (from Product Data)

  • Product name: 2-Chloro-4-(2-hydroxyethyl)phenol (CAS 50972-63-9)
  • SKU: C1036424
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists “456013,” which is not a standard InChIKey)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers and features (informational)

  • Molecular formula (computed from structure): C8H9ClO2
  • Molecular weight (computed): ~172.61 g/mol
  • Core scaffold: substituted phenol (tri-substituted benzene)
  • Functional groups: phenolic hydroxyl (Ar–OH), benzylic primary alcohol (–CH2–CH2–OH), aryl chloride (Ar–Cl)
  • Substitution pattern (described in words): Phenolic OH at ring position 1; chloro at the 2-position (ortho to OH); 2-hydroxyethyl at the 4-position (para to OH). The two hydroxyl groups are not conjugated with each other; one is phenolic, the other is aliphatic.

• 2D structure description (in words)

  • Aromatic ring bearing: (i) an OH substituent, (ii) a chlorine ortho to that OH, and (iii) a –CH2–CH2–OH para to the phenolic OH. The benzylic methylene (adjacent to the ring) and terminal alcohol define a flexible, polar side chain.

Synthetic Utility

Functional group set and strategic value (literature/general)

• Phenolic OH (Ar–OH): Nucleophile after deprotonation; amenable to O‑alkylation/acylation, carbonate/urethane formation, Mitsunobu couplings, and conversion to aryl triflate (Ar–OTf) for cross‑coupling.
• Primary alcohol (–CH2–CH2–OH): Versatile handle for oxidation (aldehyde/acid), activation (tosylate/mesylate/halide), or intramolecular cyclizations. Benzylic positioning can facilitate selective transformations.
• Aryl chloride (Ar–Cl): Platform for Pd/Ni‑catalyzed C–C/C–N/C–O couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Negishi) with appropriate ligands and bases.

Orthogonal protection/exploitation

• Differential protection of phenol vs. primary alcohol enables sequential chemistries. For example, protect phenol as TBDPS ether, oxidize side chain to aldehyde, perform reductive amination, then deprotect.
• Convert phenol to triflate to unlock rapid cross-coupling while preserving the aliphatic OH for late-stage diversification.

Retrosynthetic/logistic advantages

• The embedded Ar–Cl is coupling‑ready without pre-halogenation; the 2‑hydroxyethyl unit offers polarity tuning in SAR series. The proximity of OH (ortho) and Cl may also enable directed metalation or orthometallation strategies after temporary phenol protection.

Purification/analysis tips

• Phenolic materials may tail on silica; add 0.5–1% Et3N or AcOH as needed. LC‑MS readily detects this mass (M+H+ ~173.6). Derivatization (silylation/acetylation) can sharpen GC profiles if volatility permits.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, ligand standard). No antigen/epitope or species reactivity information is associated with this item in the Product Data.