This compound belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.
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
150.220 g/mol
XLogP3
2.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
1
Exact Mass
150.104 Da
Monoisotopic Mass
150.104 Da
Topological Polar Surface Area
20.200 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
122.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No biological assay or immunoassay protocols are associated with this small-molecule reagent in the Product Data. For synthetic and analytical use, refer to Reaction Conditions and Solvent Selection. If employing as a reference standard, develop instrument-specific methods (e.g., GC/FID, HPLC/UV) and validate retention, purity, and response factors accordingly.
Biological Roles
This compound is a small organic benzylic alcohol primarily used as a synthetic intermediate. It is not a biological buffer, cofactor, or metabolite of canonical primary metabolism.
General chemistry context: Benzylic alcohols can undergo metabolic oxidation in biological systems to the corresponding ketones or acids; however, no specific endogenous role is attributed to 1-(2,4-dimethylphenyl)ethanol.
Research use: May serve as a reference compound in studies of benzylic oxidation, phase I metabolism models, or as a probe substrate in method development for analytical chemistry.
No medical or clinical claims are made. For research use only (per Product Data). If biological interaction data are needed, consult the primary literature for this exact substitution pattern.
Buffer Applications
Not typically applicable. 1-(2,4-Dimethylphenyl)ethanol is not a buffering agent and is not used to prepare aqueous buffer systems. For work involving this compound, see Reaction & Applications, Synthetic Utility, and Solvent Selection for more relevant guidance.
Green Alternatives
Although this product is a substrate (not a solvent), greener choices can be made for its common transformations. Examples (literature/general):
Oxidation to ketone:
Greener option: TEMPO/bleach (NaOCl) in water/organic biphasic systems or Oxone®/catalytic TEMPO, avoiding chromium(VI) reagents.
Trade-offs: Emulsion handling and pH control are required; risk of over-oxidation of benzylic methyls under aggressive conditions.
Esterification:
Greener option: Carbodiimide-free approaches using acid anhydrides with catalytic DMAP in EtOAc or 2-MeTHF; or Steglich variants replacing DCM with EtOAc or CPME.
Trade-offs: Byproduct separation and odor (e.g., isobutyl byproducts) may require process optimization.
Mitsunobu-type substitution:
Greener option: Use PMe3·HBr/DIAD alternatives or catalytic Mitsunobu variants; explore azodicarboxylate surrogates and solvent swaps (2-MeTHF, EtOAc).
Trade-offs: Scope limitations and lower reactivity with hindered substrates.
Dehydration/elimination:
Greener option: Solid acid catalysts (Amberlyst-15, H-BEA) in toluene or solvent-free conditions under reduced pressure.
Trade-offs: Temperature control and selectivity between E/Z or positional isomers.
Small comparison (illustrative):
DCM vs EtOAc: EtOAc offers lower toxicity and better environmental profile; may demand base scavengers and can dissolve DMAP effectively.
THF vs 2-MeTHF: 2-MeTHF is bio-based, higher boiling (easier water removal), and often enables better phase separation; may complicate very low-temperature work due to higher freezing point.
General guidance: Prefer catalytic over stoichiometric heavy-metal oxidants, choose safer solvents per solvent selection guides (Pfizer/ACS), and design telescoped processes to limit solvent exchanges.
Pharmaceutical Uses
This product is not an excipient listing and has no pharmacopeial monograph specified here.
Potential roles (general, non-clinical): May serve as a synthetic intermediate en route to aryl ethanones (ketones), ethers, esters, or as a reference standard in analytical method development.
Regulatory status: Not specified for this item; refer to CoA/Spec Sheet for any compendial or regulatory notes if applicable.
No therapeutic or clinical claims are made. For research use only (per Product Data).
Physical Properties
Item-specific specs (this lot): Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical properties for this structure (for reference; not specifications):
Phase/appearance: typically a colorless to pale yellow liquid for many benzylic secondary alcohols in this MW range.
Boiling point: benzylic secondary alcohols such as 1-phenylethanol boil >200 °C; 2,4-dimethyl substitution generally increases the boiling point further (literature trend).
Melting point: often below ambient for analogous aryl secondary alcohols; specific value not confirmed in standard references for this substitution pattern.
Density: expected around 0.95–1.00 g/mL at 20–25 °C for related aryl alcohols; exact value not confirmed for this compound.
Refractive index: aryl alcohols typically nD20 ≈ 1.50–1.54; specific value not confirmed.
Solubility (qualitative):
Water: low solubility is expected due to the two ring methyls increasing hydrophobicity compared with 1-phenylethanol.
Organic solvents: miscible with many common organics (Et2O, THF, DCM, EtOAc, toluene, alcohols) per behavior of benzylic alcohols.
LogP: increased relative to 1-phenylethanol due to two additional methyl groups; specific number not verified.
pKa (O–H): phenethyl-type secondary alcohols typically pKa ≈ 16–18 in water/MeOH (literature). Exact pKa for this derivative not confirmed.
Notes:
Use these values only as general guidance. For precise method development or engineering calculations, verify with primary literature or measure experimentally for the actual lot.
Quality and Grades
Item-specific 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
Analytical/Reagent grades: When offered as analytical reagent (AR) or ≥98% purity, aryl alcohols are suitable for synthesis, method development, and reference use. Low UV-absorbance solvents/solutes are important for HPLC/UV detection; for analytes like benzylic alcohols, trace aromatic impurities can bias baselines.
Impurity considerations: Typical impurity profiles for benzylic alcohols may include the corresponding ketone (oxidation), unreacted aromatic precursors, and water. If your application is moisture- or oxidation-sensitive (e.g., Mitsunobu, selective oxidations), request lot-specific Karl Fischer and residual solvent data where applicable.
UV profile: For chromatographic applications, low UV background is advantageous; however, item-specific UV cutoffs are Not specified for this item; refer to CoA/Spec Sheet.
Metal content/ions: Not specified for this item; refer to CoA/Spec Sheet.
Guidance
For stereochemical studies, request enantiomeric ratio or optically active material if needed. Racemic material is typically supplied unless stated otherwise.
For quantitative work, consult the CoA for assay method, purity by GC/HPLC, and identity confirmation (NMR/IR/MS). Ensure specifications match your compliance needs (e.g., residual solvents, RoHS/REACH where relevant).
Reaction and Applications
As a benzylic secondary alcohol, 1-(2,4-dimethylphenyl)ethanol serves both as a synthetic intermediate and as a handle for constructing substituted aryl ethanes/ketones/ethers.
Oxidation to ketone: Conversion to 2,4-dimethylacetophenone via Swern, Dess–Martin periodinane (DMP), TEMPO/bleach (NaOCl, biphasic), MnO2, or catalytic Ru/Fe systems. Benzylic activation enables high selectivity and mild conditions.
Esterification/Carbonylation: Formation of benzylic esters (acyl chlorides/anhydrides/EDC·HCl + DMAP). Useful for derivatization and as leaving-group precursors.
Mitsunobu substitution: Inversion at the benzylic stereocenter to install O-, N-, or S-nucleophiles (DEAD/DIAD + PPh3 or greener alternatives) yielding benzylic ethers, azides, etc.
Dehydration/Elimination: Acid-catalyzed dehydration to give the corresponding 1-(2,4-dimethylphenyl)ethylene (styrenyl) isomer(s); leverage benzylic cation stability.
Reductive methods: Convert to 2,4-dimethylethane derivatives via hydrogenolysis of activated derivatives (e.g., tosylates) or Barton–McCombie conditions (after xanthate formation).
Friedel–Crafts-type transformations: The benzylic alcohol can be transformed into a cationic intermediate under strong acid to effect intramolecular or intermolecular alkylations (use caution; rearrangements possible).
Practical tips:
Moisture control is beneficial for carbocation-mediated or acylation chemistry; dry solvents and glassware improve reproducibility.
Monitor for over-oxidation to benzoic acids under vigorous oxidative conditions; aryl methyl substituents can also oxidize under harsh reagents.
If stereochemistry matters, begin from enantioenriched starting material or resolve the alcohol prior to Mitsunobu or acylation steps.
Reaction Conditions
General literature guidance for typical transformations (non-binding; optimize for your system):
Oxidation to ketone (2,4-dimethylacetophenone)
Dess–Martin periodinane (DMP): 1.3–1.5 equiv DMP, CH2Cl2, 0 °C to rt, 1–3 h; typical isolated yields 80–95% for benzylic alcohols.
TEMPO/NaOCl: 2–5 mol% TEMPO, KBr cocatalyst, pH ~9–10 aqueous NaOCl with CH2Cl2 or EtOAc as organic phase, 0–5 °C to rt, 0.5–2 h; quench with Na2S2O3.
MnO2 (activated): 5–10 wt equiv, CH2Cl2 or toluene, rt to reflux, 2–24 h; monitor to prevent over-oxidation of benzylic methyls under harsh conditions.
Esterification/Acylation
Acyl chloride (e.g., benzoyl chloride): 1.1–1.5 equiv, Et3N or pyridine, catalytic DMAP, CH2Cl2 or EtOAc, 0 °C to rt, 1–4 h; typical yields 80–95% for benzylic alcohols.
Steglich (EDC·HCl/DMAP): carboxylic acid (1.2 equiv), EDC·HCl (1.2–1.5 equiv), catalytic DMAP, CH2Cl2/EtOAc, 0 °C to rt, 2–12 h.
Mitsunobu substitution (inversion)
Alcohol (1.0 equiv), pronucleophile (1.2–2.0 equiv, pKa < 11), DIAD/DEAD (1.2–1.5 equiv), PPh3 (1.2–1.5 equiv), THF or toluene, 0 °C to rt, 2–8 h; typical yields 60–90% depending on nucleophile.
Dehydration to alkene
p-TsOH (5–10 mol%), toluene or xylene, Dean–Stark, 90–130 °C, 2–6 h; or POCl3/pyridine at 0 °C→rt. Expect E/Z or positional isomer distribution typical of benzylic eliminations.
Notes:
Dry, oxygen-poor conditions improve outcomes for sensitive steps. Use silica-gel pretreatment or base washes to remove acids postreaction when preserving alcohol stereochemistry.
Always confirm with small-scale trials and adapt to the exact substitution pattern and desired selectivity.
Safety and Handling
Item-specific hazard information from Product Data
GHS classification: Not specified for this item; refer to SDS.
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H-codes): Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for benzylic secondary alcohols (informational; consult SDS for authoritative guidance)
Likely hazards: May cause irritation to eyes/skin; ingestion or inhalation of vapors/aerosols may be harmful. Combustible liquid at elevated temperature; keep away from ignition sources.
PPE: Safety glasses or goggles, lab coat, appropriate chemically resistant gloves (e.g., nitrile), and good laboratory ventilation. Use fume hood for operations that generate vapors or aerosols.
Handling: Avoid breathing vapors/mist. Prevent contact with strong oxidizers (may promote exothermic reactions/oxidation). Avoid strong acids/bases that can catalyze dehydration/etherification.
Storage incompatibilities: Separate from oxidizing agents (e.g., peroxides, chromium(VI) reagents), strong reducing agents, acid chlorides/anhydrides (acylation hazard), and strong bases if long-term stability is critical.
First aid (overview):
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention.
Skin contact: Wash with soap and water; remove contaminated clothing.
Inhalation: Move to fresh air; monitor for respiratory irritation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire response: Use CO2, dry chemical, or alcohol-resistant foam. Vapors may form explosive mixtures with air at elevated temperatures.
Waste: Dispose according to local regulations; organic waste stream for alcohols.
Always defer to the product’s SDS for definitive hazard classification and response measures.
Solvent Selection
This product is a substrate/reagent (an aryl secondary alcohol), not typically used as a chromatography or process solvent. Nevertheless, its solvation behavior informs reaction design.
Miscibility/solubility: Generally soluble in ethers (THF, MTBE), chlorinated solvents (DCM, CHCl3), esters (EtOAc), aromatics (toluene), alcohols (MeOH, EtOH, i-PrOH), and hydrocarbons (heptane) to varying degrees. Water solubility is expected to be low due to 2,4-dimethyl substitution increasing hydrophobicity relative to 1-phenylethanol.
Choosing media for transformations:
Oxidations to ketone: DCM, EtOAc, or acetonitrile for DMP/PCC or TEMPO systems; acetonitrile or EtOAc for green(er) TEMPO/bleach systems.
Esterifications/Acylations: DCM, THF, or toluene with DMAP/EDC, acid chlorides, or anhydrides.
Mitsunobu inversions/substitutions: THF, toluene, or DCM depending on substrate/base.
Dehydrations (to styrenyl isomer): Toluene or xylene with acid catalysts; remove water azeotropically if needed.
Comparison notes (general):
THF vs 2-MeTHF: Similar polarity; 2-MeTHF offers improved sustainability and water tolerance.
DCM vs EtOAc: EtOAc is less hazardous and often suitable for acylations/extractions but may require base scavenging management.
Always verify solubility and stability experimentally for your specific conditions and scale.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place. Keep away from heat, ignition sources, and strong oxidizers.
Container recommendations: Use amber glass to minimize photochemical discoloration; employ PTFE-lined caps for solvent resistance. If repeatedly opening, consider inert gas blanket (N2/Ar) to minimize slow aerobic oxidation to the corresponding ketone.
Stability: Benzylic alcohols are generally stable under ambient conditions. Avoid prolonged exposure to strong acids/bases to prevent dehydration or transesterification.
Reconstitution: Not applicable; supplied neat. If dilution is required for handling or standard preparation, use a compatible anhydrous solvent (e.g., EtOAc, DCM, THF, MeOH) and record exact concentrations.
Freeze–thaw: Not relevant for neat liquids; if preparing solutions, store at appropriate temperatures and avoid repeated freeze–thaw cycles that can change concentration by solvent loss.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
General good practice: Record receipt date and lot number, minimize headspace for long-term storage, and periodically check by GC/HPLC/NMR for signs of oxidation or dehydration if the material is mission-critical.
Structure and Identity
Brief description: 1-(2,4-Dimethylphenyl)ethanol is a benzylic secondary alcohol bearing methyl substituents at the 2- and 4-positions of the aromatic ring.
Item-specific identifiers from Product Data
CAS: 5379-19-1
SKU: E693730
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a truncated value: "67907")
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/representative identity (for reference only; not item-specific specifications)
Common name: 1-(2,4-Dimethylphenyl)ethanol (aka 2,4-dimethyl-1-phenylethanol)
Representative SMILES (literature): CC(O)c1ccc(C)cc1C (one of several equivalent notations)
Representative InChIKey (literature): commonly reported for this structure; consult public databases for confirmation.
Approximate molecular formula (literature): C10H14O
Functional groups: secondary alcohol (benzylic), substituted aromatic ring (o,p-dimethyl pattern).
Benzylic stereocenter: the carbinol carbon is stereogenic in substituted derivatives; this substance is typically obtained as a racemate unless resolved.
2D description: a monosubstituted 1-phenylethanol core where the phenyl ring also carries two methyl groups at positions ortho (2) and para (4) relative to the benzylic alcohol substituent.
Electronic characteristics: benzylic position stabilized by resonance; ring methyl groups are weakly electron-donating (hyperconjugation), slightly activating the ring toward electrophilic substitution.
Synthetic Utility
Key reactivity features of 1-(2,4-dimethylphenyl)ethanol (general/literature):
Benzylic activation: The secondary benzylic alcohol forms stabilized carbocations or participates in SN1-like processes under acidic conditions, enabling dehydration to styrenes and substitution to install nucleophiles.
Oxidation handle: Mild oxidants (DMP, TEMPO, MnO2) convert it to 2,4-dimethylacetophenone, a versatile building block for further transformations (e.g., oxime formation, halogenation at the benzylic position, or Friedel–Crafts acylation analogs).
Protection/Derivatization: Formation of carbonates, benzoates, or silyl ethers (e.g., TBS) can modulate reactivity or provide leaving groups for downstream chemistry.
Stereochemical manipulations: The carbinol carbon is a potential stereocenter. Mitsunobu reaction affords inversion with O-, N-, or S-nucleophiles. Chiral resolution or asymmetric reduction routes can furnish enantioenriched variants for SAR studies.
Cross-coupling adjacency: While the alcohol itself is not a coupling handle, converting to the corresponding benzylic halide, mesylate, or triflate can allow subsequent substitution or even nickel/iron-catalyzed cross-electrophile coupling to form C–C bonds.
C–H functionalization: The 2,4-dimethyl aryl ring can undergo directed or nondirected functionalization (e.g., benzylic C–H oxidation) under modern catalytic conditions; caution with over-oxidation of methyl substituents.
Strategic value: Serves as a branch point enabling access to ketones, alkenes, ethers/esters, and deoxygenated benzylic products while preserving or exploiting the 2,4-dimethyl ring electronics.
Target Specificity
Not applicable. This product is a small-molecule reagent/intermediate, not a biological targeting agent (e.g., antibody, peptide, or probe). No antigen, epitope, clone, isotype, or species reactivity information applies.
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