2-(1-Hydroxyethyl)phenol - ≥95% , CAS No.62019-23-2

CAS: 62019-23-2 Cat. No.: H1023984 Formula: C₈H₁₀O₂ Molecular Weight: 138.160

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

CC(C1=CC=CC=C1O)O

IUPAC Name

2-(1-hydroxyethyl)phenol

InChIKey

JVNCFFFHVBWVBR-UHFFFAOYSA-N

INCHI

1S/C8H10O2/c1-6(9)7-4-2-3-5-8(7)10/h2-6,9-10H,1H3

Molecular Weight

138.160

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenols
      • Subclass 1-hydroxy-4-unsubstituted benzenoids

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenols
• Subclass: 1-hydroxy-4-unsubstituted benzenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: 1-hydroxy-4-unsubstituted benzenoids
• Alternative Parents: 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Secondary alcohols Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Aromatic alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
• 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

Chemical and Physical Properties

• Molecular Weight: 138.160 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 138.068 Da
• Monoisotopic Mass: 138.068 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 103.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 assay or immunoassay protocols are specified for this small-molecule reagent.

General laboratory usage suggestions (non-binding, literature-based):

• Preparation of stock solutions: Dissolve in DMSO, MeOH, or EtOH to prepare concentrated stocks (e.g., 10–100 mM), then dilute into reaction media or assay buffers as needed, ensuring final cosolvent ≤1–2% v/v for biochemical assays.
• Synthetic runs: For oxidations/acylations described in the Reaction Conditions tab, scale a small pilot reaction (0.1–1 mmol) to confirm selectivity between phenolic and secondary alcohol functionalities before scale-up.
• Analytical characterization: Verify identity/purity by 1H/13C NMR (phenolic OH often broad/suppressed; observe benzylic methine), IR (broad O–H ~3200–3600 cm−1; Ar–O stretch), and LC–MS.

For any validated, method-specific protocols, please refer to publications or develop internal SOPs. Item- and lot-specific instructions are not provided for this SKU.

Biological Roles

Scope: This product is intended for research use only. No clinical or therapeutic claims are made.

General biochemical context (literature-based):

• Phenolic motifs: Phenolic groups can participate in hydrogen bonding and redox chemistry; substituted phenols are common in natural products and can act as radical scavengers in model systems. However, 2-(1-hydroxyethyl)phenol itself is not known as an endogenous metabolite.
• Enzyme interactions: Phenols may interact with oxidative enzymes (peroxidases, laccases) and undergo enzymatic oxidation to quinone-like species in vitro. A neighboring benzylic alcohol could be enzymatically oxidized to the corresponding ketone by alcohol dehydrogenases in model systems.
• Membrane interactions: Dual hydroxylation increases polarity versus alkylphenols, reducing membrane partitioning (lower logP relative to alkylphenols) and potentially increasing aqueous compatibility in biochemical assays.

Laboratory considerations:

• For biochemical assays, solvent choice (e.g., DMSO cosolvent) and pH control are critical because the phenolic group deprotonates near basic pH, altering binding and spectroscopic properties.
• Adsorption: Phenolic compounds can adsorb to plastics; use glassware for accurate dosing.

Note: Any biological activity assays should be designed and interpreted within a basic research framework. Verify purity and absence of interfering phenolic impurities (which can have disproportionate redox effects) using appropriate analytical methods (HPLC, LC–MS).

Buffer Applications

Not typically applicable. 2-(1-Hydroxyethyl)phenol is not a standard buffering reagent. While phenolic pKa values are around ~10 (literature), making conjugate phenoxide/phenol pairs in principle usable near alkaline pH, this compound is rarely, if ever, employed as a buffer component due to reactivity, potential oxidative instability, and lack of defined buffering capacity data.

Practical guidance for laboratory use:

• If preparing aqueous solutions for assays, use a conventional buffer system (e.g., phosphate, Tris, HEPES) appropriate to the target pH, and dissolve this compound as a solute (often with a small amount of DMSO or ethanol cosolvent to aid solubility).
• Avoid strong alkaline conditions unless phenoxide formation is intended, as deprotonation will alter solubility/spectral properties and may complicate biological readouts.

For specifications on solution stability, pH-dependent solubility, or extinction coefficients, consult literature data or generate internal characterization under your exact conditions.

Green Alternatives

Although this product is a reagent/building block (not a solvent), greener choices can be made in processing and transformations involving 2-(1-hydroxyethyl)phenol.

• Solvent selection (comparative, literature-based):

  • Prefer bio-based ethers/esters (e.g., 2-MeTHF, CPME, EtOAc) over chlorinated solvents (DCM, CHCl3) when compatible with reactivity and workup.
  • For oxidations to the ketone, use catalytic TEMPO/bleach or O2/NOx systems in water/MeCN mixtures as alternatives to stoichiometric chromium reagents.
  • For acylations, solvent-free or EtOAc-based protocols with recyclable bases (solid-supported) can reduce waste.

• Example comparison (general):

  • DMP in DCM vs. TEMPO/NaOCl in MeCN/H2O: The latter avoids halogenated organic solvents and heavy iodine waste; workup generates brine/benign salts but may require careful pH control.
  • Swern oxidation (DMSO/oxalyl chloride) vs. catalytic IBX or electrochemical oxidation: Electrochemical methods may eliminate stoichiometric oxidants but require setup and optimization.

• Workup and purification:

  • Replace silica-heavy purifications with crystallization or liquid–liquid extraction when possible; consider supercritical CO2 for analytical purification.

Tradeoffs: Greener choices may affect selectivity (phenol vs. secondary alcohol), reaction rate, and isolation efficiency. Pilot small-scale experiments to confirm equivalence before scale-up.

Pharmaceutical Uses

Formulation/excipient role: Not a common pharmaceutical excipient. No pharmacopeial monograph is known for 2-(1-hydroxyethyl)phenol.

Relevant context for drug discovery and process chemistry (literature-based, non-clinical):

• Intermediate: The compound serves as a useful intermediate toward o-hydroxyacetophenone derivatives and benzofuran scaffolds, motifs frequently explored in medicinal chemistry campaigns.
• Protecting-group strategies: Orthogonal protection of the phenolic and secondary alcohol functionalities allows stepwise derivatization for SAR exploration.
• Salt formation: Phenols typically do not form stable pharmaceutically acceptable salts except as phenolates; transient base forms can aid crystallization or purification during process development.
• Analytical control: If used in screening libraries, ensure low peroxide content is not a concern (phenols are less prone than ethers) and monitor oxidative degradation under light/air to maintain consistent assay performance.

All uses are limited to research and development. This product is not intended for human or veterinary use, diagnostic procedures, or as a drug substance/excipient in marketed products.

Physical Properties

Item-specific specifications (this lot):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: 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 properties (reference only; not product specifications):

• Empirical formula (literature): C8H10O2
• Formula weight (literature): ~138.16 g/mol
• Physical state: typically a low-melting solid or viscous liquid depending on purity and temperature (literature, general for ortho-phenolic benzylic alcohols).
• Polarity/functional profile: bifunctional, H‑bond donor/acceptor; phenolic pKa typically near ~10; aliphatic alcohol pKa ~16–18 (literature, class values). Phenol is the more acidic site.
• Solubility (qualitative, literature):
  • Miscible or highly soluble in polar organics (MeOH, EtOH, acetone, acetonitrile, DMF, DMSO)
  • Moderately soluble in moderately polar solvents (EtOAc)
  • Limited solubility in aliphatic hydrocarbons; enhanced in aromatics (toluene) via π–π interactions
  • Some water solubility expected due to two OH groups, but typically moderate.
• Volatility: substantially lower than simple alkylphenols due to dual hydrogen bonding (literature trend).

Note: For authoritative values such as mp/bp, density, refractive index, water content, and UV cutoff, refer to the CoA/Spec Sheet for this specific SKU.

Quality & Grades

Item-specific grade/purity and stabilizers:

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

Context for professional users:

• Research-grade vs. analytical/HPLC grade: In the absence of a declared grade, users should evaluate suitability for purpose by reviewing the CoA (assay, GC/HPLC purity, major impurities) and the UV profile if chromatographic detection is anticipated. HPLC grade materials feature low UV background and tight control of trace impurities relevant to chromatography; research grade emphasizes fitness for synthetic use.
• Trace specifications: If your application is metal- or moisture-sensitive (e.g., organometallic catalysis), confirm water, peroxide (not typically relevant for phenolics), and metal content on the CoA. Where specifications are not listed, consider performing in-house Karl Fischer or ICP analyses.
• Stabilizer implications: Phenols sometimes ship without stabilizer; if a stabilizer is present, it will be listed on the CoA and may need removal (e.g., by aqueous wash, adsorption, or distillation/recrystallization) before sensitive transformations.

Recommendation: For reproducibility in synthesis or assay development, archive the CoA specific to SKU H1023984 and lot, and reference it in methods. If enantiopurity is critical, confirm optical activity or enantiomeric ratio on the CoA; otherwise assume racemic material.

Reaction & Applications

This ortho-phenolic benzylic secondary alcohol is a versatile synthon for aromatic construction and fine-chemical research. Typical applications (literature-based; expand from the compound’s functional profile):

• Oxidation to o-hydroxyacetophenone: The secondary alcohol is readily oxidized to the corresponding ketone using Dess–Martin periodinane (DMP), Swern, PCC, or catalytic TEMPO/bleach. o-Hydroxyacetophenones are valuable in chalcone formation, heterocycle synthesis (e.g., benzoxazoles), and as ligands.
• Selective acylation/alkylation: Phenolic OH can be selectively acylated (Ac2O, acid chlorides) or alkylated (Williamson conditions via phenoxide) to tune reactivity or create protecting groups. Orthogonal protection strategies exploit differing acidity/nucleophilicity of the two OH groups.
• Mitsunobu chemistry: The secondary alcohol can undergo substitution/inversion under Mitsunobu conditions with suitable nucleophiles; care is needed to avoid concurrent phenolic participation.
• Cyclization/ether formation: Intramolecular etherification (after activation) can access benzofuran frameworks under acidic/dehydrative conditions.
• Ester/Carbonate formation: Preparing carbonates or esters from the secondary alcohol generates leaving groups for further transformations or enables polymer-precursor exploration.
• Metal-directed ortho chemistry: Deprotonation to phenoxide enables chelation-assisted transformations (e.g., directed ortho-metalation on suitably functionalized derivatives).

Practical tips:

• Drying: If water-sensitive steps are planned, dry by azeotrope or co-evaporation; store over molecular sieves to limit hydration.
• Acid/base control: Use stoichiometric base for phenoxide formation; weaker bases (Na2CO3) may suffice for acylations, while stronger bases (NaH, K2CO3) are typical for O‑alkylations.

Reaction Conditions

General literature guidance for common transformations of 2-(1-hydroxyethyl)phenol (not product specifications):

• Oxidation to o-hydroxyacetophenone:

  • DMP: 1.5–2.0 equiv in dry DCM, 0–25 °C, 1–3 h; typically high conversion with minimal over-oxidation. Quench with aqueous NaHCO3 and Na2S2O3.
  • Swern: DMSO/oxalyl chloride at −78 to −40 °C, followed by base (Et3N); efficient for sensitive substrates.
  • TEMPO/NaOCl: Catalytic TEMPO (2–5 mol%), NaOCl (1.5–2.0 equiv active Cl) in MeCN/H2O, 0–25 °C; buffer near pH 8–9.

• Phenolic O‑acylation/alkylation:

  • Base: K2CO3 or NaH in acetone, MeCN, THF, or DMF; 0–60 °C, 1–12 h. For selective phenol acylation, pyridine or DMAP catalysis with acyl chlorides/anhydrides in DCM/MeCN is effective.

• Benzylic alcohol derivatization:

  • Formation of mesylate/tosylate: MsCl or TsCl, Et3N, catalytic DMAP, DCM, 0–25 °C; then SN1/SN2 substitution depending on nucleophile.
  • Mitsunobu: DEAD/DIAD, PPh3 in THF/THF–toluene, 0–25 °C; monitor for competing phenolic reaction—protect if necessary.

• Intramolecular cyclization (to benzofurans):

  • Acid-catalyzed dehydration after activation can proceed in toluene or xylene under reflux with water removal.

• Analysis and control:

  • TLC with UV and anisaldehyde/vanillin stains detects phenolic species.
  • Maintain anhydrous conditions for base-promoted steps; employ molecular sieves when appropriate.

Reported yields vary with substitution/protecting strategy; consult primary literature for substrate-matched optimization.

Safety & Handling

Item-specific hazard information:

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

General safety considerations for phenolic secondary alcohols (literature-based; not a substitute for the SDS):

• Likely hazards: phenolics are commonly irritating to skin/eyes and may be harmful if swallowed; avoid inhalation of vapors/aerosols. Secondary benzylic alcohols can be combustible.
• PPE: wear appropriate lab coat, safety glasses or splash goggles, and chemically resistant gloves (e.g., nitrile); use in a chemical fume hood.
• Handling: minimize exposure; avoid heat, sparks, and open flames. Prevent contact with strong oxidizers (may promote exothermic oxidation) and strong bases (can form reactive phenoxides; exothermic neutralization).
• Storage incompatibilities: segregate from oxidizing agents, strong bases, acid chlorides/anhydrides (which may acylate), and reactive metals.
• First aid (overview; defer to SDS):
  • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: move to fresh air; seek medical advice if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; consult medical attention.
• Special risks: phenolic materials can slowly oxidize/discolor on air exposure; keep containers tightly closed and limit headspace air if long-term storage is intended.

Always consult the product SDS for definitive hazard and response information.

Solvent Selection

Applicability: This product is a bifunctional aromatic alcohol (not a solvent). Solvent selection guidance below pertains to dissolving/processing this compound in reactions or preparations.

• Polarity class and interactions (general):

  • Exhibits strong hydrogen-bonding as donor and acceptor; dissolves well in polar protic (MeOH, EtOH) and polar aprotic solvents (DMF, DMSO, acetonitrile). Solubility is moderate in less polar media (EtOAc, toluene) and limited in alkanes.
  • Phenolic acidity is enhanced in polar solvents; deprotonation (to phenoxide) is favored in basic, polar aprotic media (e.g., DMF, DMSO, THF) enabling O‑alkylation/acylation.

• Practical choices by task (literature-based):

  • Purification: Flash chromatography using hexanes/EtOAc or toluene/EtOAc gradients; addition of a few percent of Et3N or AcOH can suppress streaking of phenols.
  • Protection/acylation: Use dry DCM, THF, MeCN, or pyridine/Et3N as base/solvent; control water content for selective acylation of phenol vs. secondary OH.
  • Oxidation to o-hydroxyacetophenone: DCM, EtOAc, or MeCN are common with DMP, Swern, or TEMPO/bleach systems.
  • Metalation/cross-coupling (after converting to aryl halide/boronate): Use polar aprotics (THF, dioxane, MeCN) under anhydrous conditions.

• Comparison (typical):

  • MeOH/EtOH: high solubility; good for analytical prep and NMR.
  • EtOAc/toluene: good for workups and extractions while maintaining phase separation.
  • DMSO/DMF: excellent solubility; consider downstream removal challenges.

Storage & Reconstitution

Item-specific storage conditions:

• Storage Conditions: Room temperature (per Product Data).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for this class of compounds (literature-based):

• Container: Store tightly closed in amber glass to limit light exposure; phenolic compounds can slowly oxidize/discolor upon prolonged air/light exposure.
• Atmosphere: For long-term storage, consider minimizing headspace air or backfilling with inert gas, especially if repeated openings are expected.
• Moisture: Keep dry; while not highly hygroscopic, the presence of water can influence acylation/alkylation selectivity and stability in certain reactions.
• Temperature excursions: Room temperature is acceptable; avoid excessive heat. Refrigeration is typically not required but can extend shelf life if compatible with handling practices (prevent condensation on warm-up).

Reconstitution/solution preparation:

• Solubility: Readily soluble in common polar organic solvents (DMSO, MeOH, EtOH, acetone, MeCN). If aqueous use is required, prepare a concentrated stock in DMSO or EtOH and dilute into buffer with vigorous mixing.
• Freeze–thaw: If storing solutions, aliquot to avoid repeated freeze–thaw cycles which may introduce moisture/oxygen and accelerate degradation.

Always consult the CoA and SDS for lot-specific guidance.

Structure & Identity

Brief overview: 2-(1-Hydroxyethyl)phenol is an ortho-disubstituted phenolic building block bearing a phenolic OH and a benzylic secondary alcohol at the 2-position (–CH(OH)–CH3), creating a single stereogenic center (typically supplied as racemate unless otherwise noted).

• Item-specific identifiers (from Product Data):

  • CAS: 62019-23-2
  • CID: 10866399
  • InChIKey: 171211 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature structural information (for reference; not item-specific):

  • Typical molecular formula: C8H10O2 (literature)
  • Typical molecular weight: ~138.16 g/mol (literature)
  • Functional groups: phenolic hydroxyl (Ar–OH), secondary benzylic alcohol (–CH(OH)–CH3)
  • Stereochemistry: one stereogenic center at the benzylic carbon; racemic mixtures are common in commerce unless enantioenriched material is specified.

• 2D structural description (general):

  • A benzene ring bearing two adjacent substituents in the ortho (1,2) relationship: at position 1 a phenolic OH, at position 2 a 1-hydroxyethyl group. This confers intramolecular H‑bonding potential between the phenolic OH and the neighboring alcohol, and enables chelation to metals upon deprotonation of the phenol (phenoxide).

Synthetic Utility

Key functional features enabling synthesis (literature-based):

• Phenolic OH: Acidic (pKa ~10), readily deprotonated to phenoxide for O‑alkylation/acylation; serves as a directing/chelating group and can be protected (silyl, benzyl, carbonate) to manage chemoselectivity.
• Secondary benzylic alcohol: Oxidizable to ketone (o-hydroxyacetophenone), convertible to halides/esters/mesylates for subsequent substitution or elimination; stereogenic center allows access to enantioenriched derivatives via resolution/asymmetric synthesis.

Representative transformations:

• Oxidation: DMP, Swern, PCC, or catalytic TEMPO/bleach to form o-hydroxyacetophenone.
• Mitsunobu substitution: Install heteroatoms at the benzylic center with inversion; manage competing phenol reactivity by prior protection or selective activation.
• O‑Alkylation/etherification: Williamson conditions (NaH/K2CO3; alkyl halide) to aryl ethers; phase-transfer catalysis can be effective with milder bases.
• Esterification/carbonate formation: Activate the secondary alcohol to tune leaving group propensity for further elaboration.
• Cyclodehydration to benzofurans: After activation, intramolecular cyclization can furnish benzofuran cores.

Retrosynthetic value:

• Serves as a masked o-hydroxyacetophenone and as a bifunctional handle for divergent synthesis: derivatize the ring (after halogenation/metalation) while independently transforming the side chain.

Practical notes:

• Control chemoselectivity by differential protection; monitor via 2D NMR (HMBC/HSQC) to distinguish O‑ vs. C‑acylation.
• Use non-nucleophilic bases for selective phenoxide formation when the benzylic alcohol must remain unmodified.

Target Specificity

Not applicable. This product is a small-molecule reagent and is not an antibody, enzyme, or affinity reagent. No target specificity data (antigen/epitope, species reactivity, clone, isotype) are associated with this item.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 62019-23-2, the molecular formula is C8H10O2, and the molecular weight is 138.160 g/mol. InChIKey JVNCFFFHVBWVBR-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.