This compound belongs to the class of organic compounds known as para cresols. These are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.
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
138.160 g/mol
XLogP3
1.000
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
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
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
Not applicable. No tested bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule building block. For synthetic and analytical uses, refer to the Reaction Conditions and Solvent Selection sections for practical guidance.
If preparing stock solutions for biochemical assays:
Dissolve in DMSO (e.g., 10–100 mM), then dilute into assay buffer keeping final DMSO ≤1–2% v/v to minimize biological interference (general lab practice).
Filter sterilize through 0.22 µm PTFE if sterility is required. Verify solubility and stability at working pH.
Biological Roles
No product-specific biological data are provided. The information below reflects general knowledge about small phenolic/benzylic alcohol compounds and should not be taken as properties of this specific lot.
Phenolic functionality: Phenols can participate in hydrogen bonding and redox processes and are common motifs in natural products (lignin-derived fragments, plant phenolics). They can act as radical scavengers/antioxidants in model systems (literature/general), though activity depends strongly on substitution pattern and conditions.
Benzylic alcohols: Frequently arise as intermediates in the metabolism of methyl-substituted aromatics (via benzylic oxidation), and can be further oxidized to aldehydes/acids by dehydrogenases in biological systems (general biochemistry).
Physicochemical profile: A compound with one phenolic OH and one benzylic OH typically shows moderate polarity (capable of forming intra/intermolecular H-bonds), which can influence binding to proteins/enzymes in research assays. Ionization of the phenolic OH at basic pH can dramatically alter solubility and membrane permeability.
Utility in biochemical research: Such molecules are often used as reference substrates/inhibitors in enzymology (e.g., oxidative enzymes, transferases) or as surrogates for phenolic antioxidants in mechanistic studies (literature), subject to availability of supporting data.
Note: This product is labeled “For research use only.” No claims are made regarding biological activity, safety in vivo, or clinical suitability. For any biological testing, determine purity, counterion content (if any), and solvent vehicle compatibility in your system.
Buffer Applications
This item is not a classical buffering agent. Phenolic/benzylic alcohol compounds are not typically used to establish defined pH buffers.
If use in aqueous systems is required for research assays, dissolution generally relies on co-solvents (e.g., DMSO, ethanol) or on forming the phenolate salt with mild base, followed by dilution into the desired buffer.
For analytical HPLC in buffered mobile phases, ensure compatibility of the compound with buffer components (e.g., phosphate or ammonium formate) and consider adding 0.05–0.1% acid (formic/acetic) to sharpen peaks on reverse-phase columns.
No buffer recipes or pKa-based buffer ranges are provided for this item. For aqueous preparation guidance, consult the Reaction Conditions and Storage & Reconstitution sections and verify solubility empirically.
Green Alternatives
While the substance itself is the targeted building block, greener choices largely concern solvent and reagent selection during its use.
Greener solvent choices (literature/general):
Replace chlorinated solvents (e.g., DCM) with ethyl acetate or dimethyl carbonate when feasible (for extractions and acylations).
Use 2-methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) instead of THF/diethyl ether for many base-promoted O-alkylations; both offer improved safety/peroxide profiles and bio-based origins (2-MeTHF).
Favor ethanol or isopropanol for recrystallization over methanol where solubility permits.
Greener reagent substitutions:
Oxidations: Swap chromium(VI) reagents/PCC for Dess–Martin periodinane, IBX, TEMPO/bleach, or MnO2 depending on selectivity; aqueous TEMPO/NaOCl/NaClO2 systems are particularly attractive.
Mitsunobu alternatives: Consider PPh3/ADDP or non-Mitsunobu strategies such as catalytic acid with alcohol activation (e.g., PPA, MsCl then SN1/SN2) to avoid azodicarboxylates.
Acylations: Use acid anhydrides with catalytic DMAP rather than acid chlorides to reduce HCl generation; explore enzymatic acylations in greener solvents for selectivity.
Brief comparison (general):
DCM vs EtOAc: EtOAc has lower toxicity and is biodegradable; however, DCM offers better solvating power for some phenolic esters.
THF vs 2-MeTHF: 2-MeTHF is less miscible with water (easier workups) and more sustainable, but can have different solubility; reaction rates may change.
Waste minimization:
Employ solvent recycling, use minimal excesses of alkylating agents, and perform telescoped sequences (e.g., protect–functionalize–deprotect) to reduce isolation steps and solvent usage.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation grade is specified for this item; refer to the CoA/Spec Sheet for any regulatory information.
General, non-clinical context for this chemical class:
Synthetic intermediate: Phenolic benzylic alcohols are common building blocks for API intermediates, enabling selective O-alkylation/acylation, benzylic oxidation to aldehydes/acids, and subsequent coupling (literature/general).
Excipients: Simple phenols and benzyl alcohols are occasionally used as preservatives/solvents in formulations; however, this specific compound is not indicated for such use here and is offered strictly for research and laboratory synthesis.
Analytical standards: With appropriate characterization, related phenolic compounds may serve as system suitability or method development surrogates in chromatographic assays.
Important: This product is labeled “For research use only” and is not intended for human or veterinary use, clinical applications, or as a drug substance/excipient without further qualification.
Physical Properties
Item-specific specifications are not provided in the Product Data for this SKU. Do not use the following as product specifications; verify on the CoA/Spec Sheet.
Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for 3-(hydroxymethyl)-4-methylphenol (for context only):
Phase: typically a crystalline solid or low-melting solid due to intramolecular hydrogen bonding potential (literature/general expectation).
Solubility: sparingly soluble in water; soluble in polar organic solvents (methanol, ethanol, acetone, acetonitrile), very soluble in DMSO/DMF; limited solubility in nonpolar hydrocarbons (literature).
Acid–base behavior: phenolic OH pKa commonly ~9.5–10.5 for p-methylphenols; benzylic alcohol pKa of conjugate acid ~–2 to –3; first deprotonation occurs at phenolic OH under mild base (literature trends).
LogP/logD: phenolic benzyl alcohols often show moderate logP (approx. 1–2.5) depending on substitution; actual value for this specific compound should be confirmed (literature trends).
Refractive index, density, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Melting/boiling points: Not specified for this item; refer to CoA/Spec Sheet.
Note: Provide exact numerical properties from the CoA when planning chromatography, recrystallization, or quantitative solubility studies.
Quality and Grades
Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades and quality (general):
Analytical/Reagent grade: Typically indicates low levels of inorganic/organic impurities suitable for most synthetic work. Low water and metal content may be controlled but must be verified on the CoA.
High-purity or synthesis-grade organics: Emphasize low residual solvents and well-defined assay by GC/LC; UV profile may be relevant if the compound will be used as a reference standard.
Control strategies: GC or HPLC profiling with UV detection at 210–280 nm; 1H/13C NMR for structural confirmation; Karl Fischer for water if relevant to your application.
What to check on the CoA for this item:
Assay method and result (GC/LC area %, qNMR if available).
Identity confirmation (NMR, MS, IR, and/or HRMS).
Residual solvents and related substances profile.
Water content and appearance.
Storage statement and retest/expiry date.
Note: If low-UV applications (e.g., photochemical studies) are anticipated, request UV–Vis background data. For metal-sensitive catalysis, request trace metal analysis.
Reaction and Applications
As a bifunctional aromatic bearing a phenolic OH and a benzylic alcohol, 3-(hydroxymethyl)-4-methylphenol is a versatile intermediate for fine chemicals, materials, and medicinal chemistry.
Key application families (literature/general):
Selective protection/deprotection:
Protect phenolic OH as benzyl, silyl (TBS/TBDPS), or carbonate; protect benzylic alcohol as acetate/benzoate or silyl ether. Orthogonal strategies enable stepwise elaboration.
O-alkylation/acylation:
Phenolic O-alkylation with alkyl halides or sulfonates (K2CO3, Cs2CO3, NaH in acetone, DMF, or MeCN). Competing alkylation at the benzylic OH can be controlled by base strength and solvent.
Acylation with acyl chlorides/anhydrides (pyridine, Et3N, or DMAP catalysis) to form aryl esters and benzyl esters.
Oxidation of the benzylic alcohol:
Dess–Martin periodinane, PCC, or MnO2 afford the corresponding aldehyde; further oxidation to acid with TEMPO/bleach or Jones (chromium-free preferred).
Mitsunobu substitutions (on the benzylic OH):
Conversion to benzylic ethers/esters via PPh3/DIAD (or safer alternatives), enabling installation of diverse nucleophiles.
Electrophilic aromatic substitution (EAS):
The phenolic OH activates the ring; remaining positions (ortho/ortho′/meta′ relative to OH) can undergo halogenation, nitration (mild), sulfonylation, or Friedel–Crafts under controlled conditions.
Polymer/materials precursors:
Phenolic monomers with benzylic functionality can be used in curing resins, crosslinkers, and antioxidants (general materials chemistry practice).
Practical tips:
Drying: Brief vacuum drying or azeotropic removal of moisture improves reproducibility in O-alkylation/acylation.
Base choice: Weaker bases (K2CO3) favor phenolic deprotonation; stronger bases (NaH) will deprotonate both OH groups—consider protecting group strategies for selectivity.
Reaction Conditions
General literature guidance for transformations of 3-(hydroxymethyl)-4-methylphenol. Not item-specific; optimize per substrate and scale.
Phenolic O-alkylation:
Conditions: K2CO3 (2–3 equiv) in acetone or MeCN, alkyl halide (1.2–2 equiv), 25–60 °C, 2–16 h. For more challenging electrophiles, NaH (1.1–1.5 equiv) in DMF/THF at 0–25 °C, 1–4 h.
Notes: Control chemoselectivity vs benzylic OH by base choice (weaker base favors phenol) and solvent polarity.
Esterification/acylation:
Phenolic acylation: Acyl chloride (1.2 equiv), Et3N (2 equiv), catalytic DMAP (5–10 mol%), DCM, 0 °C to rt, 1–3 h.
Benzylic ester formation: Ac2O (2 equiv) with DMAP (5 mol%) in pyridine or DCM, 0–25 °C, 1–2 h.
Benzylic oxidation:
Dess–Martin periodinane (1.3 equiv), DCM, 0–25 °C, 0.5–2 h → aldehyde (typ. good to excellent yields in literature).
TEMPO/NaOCl (pH 8.6 buffer), CH2Cl2/H2O biphasic, 0–5 °C, 1–3 h → aldehyde; extended/modified conditions (e.g., NaClO2) afford acids.
Mitsunobu substitution (benzylic OH):
PPh3 (1.2 equiv), DIAD (1.2 equiv), nucleophile (1.5–2 equiv), THF or toluene, 0–25 °C, 2–12 h. Consider safer variants (ADDP) and waste handling.
Halogenation of benzylic OH:
PBr3 (1.1 equiv) or SOCl2 (1.2 equiv) with base, ether or DCM, 0–25 °C, 0.5–2 h → benzylic halide.
Protection strategies:
TBS protection: TBSCl (1.2–1.5 equiv), imidazole (2 equiv), DMF, rt, 2–6 h (phenol and/or benzylic OH depending on stoichiometry and catalysts).
Yields and times are typical literature ranges; monitor by TLC/LC–MS. Ensure dryness and inert atmosphere when moisture-sensitive reagents are used.
Safety and Handling
Product-specific GHS details are not provided. Always consult the SDS for authoritative safety information.
GHS classification, signal word, hazard statements, pictograms (Product Data): Not specified for this item; refer to SDS.
General safety considerations for phenolic/benzyl alcohols (literature/good practice):
Hazards: Phenols can be irritant to skin, eyes, and respiratory tract; benzylic alcohols may cause irritation. Avoid inhalation of dust/particles and contact with skin or eyes.
PPE: Use lab coat, safety goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to minimize exposure.
Incompatibilities: Strong oxidizers (risk of exothermic reaction/oxidation), strong bases (can form phenolates; enhanced reactivity), acyl chlorides/acid anhydrides (vigorous acylation), strong reducing agents (may reduce aromatic ring substituents under forcing conditions).
Special risks: Phenolic compounds can undergo air oxidation/discoloration over time. Benzylic alcohols can be oxidized to aldehydes/acids by oxidants.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill & disposal: Absorb small spills with inert material (vermiculite), collect for disposal. Dispose of contents/container in accordance with local/regional regulations.
Fire response: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and phenolic vapors; firefighters should wear SCBA.
Solvent Selection
This compound is a moderately polar aromatic diol (one phenolic OH and one benzylic OH). It dissolves well in polar organics and strongly in dipolar aprotics.
Polarity and miscibility (literature/general):
Expected to be soluble in methanol, ethanol, isopropanol, acetone, ethyl acetate, acetonitrile, DMSO, and DMF.
Sparingly soluble in water; limited solubility in alkanes and other nonpolar solvents.
Recommended solvents by use-case (general):
Stock solutions for bioassays/analytics: DMSO (high solubility, stable), or ethanol/methanol (easier removal by evaporation). Filter-sterilize if needed.
Preparative transformations: THF, MeCN, or toluene with phase-transfer/base for O-alkylation; DCM or EtOAc for acylations/esterifications (with DMAP or base); pyridine or collidine as acylation bases if selectivity is required.
Chromatography: Normal-phase silica using gradients of hexanes/EtOAc or DCM/MeOH; reverse-phase C18 with water–acetonitrile containing 0.1% acid to sharpen peaks.
Selection vs alternatives:
For greener profiles, consider 2-MeTHF or ethyl acetate instead of DCM; MeCN can often substitute for DMF or DMSO in many couplings.
If water compatibility is needed, co-solvent systems (MeCN/H2O, EtOH/H2O) with mild base can assist dissolution of the phenolic salt.
Note: Exact solubility values, UV cutoff, and water content are Not specified for this item; refer to CoA/Spec Sheet for any item-specific solvent guidance.
Shipped in (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for phenolic/benzylic alcohols:
Keep tightly closed in the original container, stored in a cool, dry place away from light and sources of oxidation. Consider using a desiccant and minimizing headspace to limit air oxidation and moisture uptake.
If long-term storage is anticipated, subdivision into aliquots under inert gas (argon/nitrogen) can reduce repeated air exposure.
Reconstitution and solution handling (general):
Solubility: Typically soluble in DMSO, DMF, methanol, ethanol, acetone, and acetonitrile; sparingly soluble in water. Verify experimentally.
Preparing stock solutions: Weigh accurately, dissolve in a compatible dry solvent (e.g., DMSO or MeOH) to a convenient concentration (e.g., 10–100 mg/mL), and store aliquots at 2–8 °C or −20 °C if extended stability is required. Protect from light if discoloration is observed.
Freeze–thaw: Avoid repeated freeze–thaw of solutions; use single-use aliquots.
Any item-specific limits such as water content, stabilizers, or retest dates are Not specified for this item; refer to CoA/Spec Sheet. Always allow the container to equilibrate to room temperature in a desiccator before opening to minimize condensation.
Structure and Identity
Short description: 3-(Hydroxymethyl)-4-methylphenol is a bifunctional aromatic building block bearing both a phenolic OH and a benzylic alcohol on a methyl-substituted benzene ring.
Product identifiers (Product Data)
SKU: H1052652
Product Name: 3-(Hydroxymethyl)-4-methylphenol
CAS: 1261454-85-6
PubChem CID: 18008098
InChIKey: 413693 (as provided; note this appears truncated relative to standard InChIKey length)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structure (general description)
Core: single benzene ring.
Functional groups: one phenolic hydroxyl (–OH) and one benzylic alcohol (–CH2OH), plus a methyl substituent (–CH3).
Substitution pattern: relative to the phenolic OH (position 1), the benzyl alcohol is at the meta position (position 3) and the methyl group is para (position 4).
Stereochemistry: none (achiral).
Composition (literature/computed, not item-specific)
A phenyl ring bearing: (1) a hydroxyl directly bound to the ring; (2) a –CH2OH substituent two carbons away from the phenolic OH (meta); and (3) a –CH3 substituent three carbons away from the phenolic OH (para). The ring is activated toward electrophilic substitution by the phenolic OH; the benzylic alcohol confers additional reactivity at the side chain.
Synthetic Utility
Functional handles and reactivity (literature/general):
Phenolic OH (Ar–OH):
Nucleophilicity enhanced upon deprotonation; undergoes O-alkylation, O-acylation, and carbonate/urethane formation.
Can be transformed into aryl ethers via Mitsunobu or via activation (e.g., triflation of the phenol to Ar–OTf followed by cross-coupling at the ipso position—requires specific conditions and is substrate dependent).
Benzylic alcohol (Ar–CH2OH):
Oxidizable to aldehyde/acid; convertible to halides (e.g., PBr3 to Ar–CH2Br) for subsequent SN2/metalation; participates in etherification/esterification.
Aromatic ring:
Activated by the phenolic OH, permitting regioselective EAS at remaining positions. Directed metalation may be possible after appropriate protection.
Retrosynthetic considerations:
Divergent synthesis: From this scaffold, parallel libraries can be generated by independently modifying the phenolic and benzylic OH groups (e.g., phenyl ether/ester arrays combined with benzylic derivatives).
Convergent routes: Access via selective hydroxymethylation (formylation/reduction) of 4-methylphenols or via substitution on 3-(halomethyl)-4-methylphenol followed by hydrolysis.
Protecting group strategy:
Phenol: TBS/TBDPS silyl ethers (imidazole/DMF), benzyl ethers (BnBr, base), or carbonates (Boc2O/DMAP) for stability under basic conditions.
Benzylic OH: Acetate/benzoate esters (Ac2O or BzCl, pyridine/DMAP) or TBS ether (TBSCl/imidazole) to permit phenolic manipulations.
Cross-coupling gateway (advanced):
After phenol activation to aryl triflate, Pd-catalyzed Suzuki/Negishi/Buchwald–Hartwig couplings can install diverse substituents, enabling rapid SAR development.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, ligand with defined biological target). No antigen/epitope, species reactivity, clone, or isotype information is provided in the Product Data.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
