Ethyl 4-(4-hydroxybutyl)benzoate , CAS No.85431-07-8

CAS: 85431-07-8 Cat. No.: E979191 Summenformel: C₁₃H₁₈O₃ Molekulargewicht: 222.280

Storage

Room temperature

Specifications

Storage

Room temperature

Namen und Kennungen

• Kanonisches Lächeln: CCOC(=O)C1=CC=C(C=C1)CCCCO
• IUPAC Name: ethyl 4-(4-hydroxybutyl)benzoate
• InChIKey: DEAHZHUWDRVSBC-UHFFFAOYSA-N
• INCHI: 1S/C13H18O3/c1-2-16-13(15)12-8-6-11(7-9-12)5-3-4-10-14/h6-9,14H,2-5,10H2,1H3
• Molekulargewicht: 222.280

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acid esters
• Alternative Parents: Benzoyl derivatives Carboxylic acid esters Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoate ester - Benzoyl - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 222.280 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 222.126 Da
• Monoisotopic Mass: 222.126 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 195.000
• 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

Not applicable. No biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule intermediate.

• Item-specific tested applications or dilutions: Not provided for this item.

Biological Roles

This product is a synthetic small-molecule intermediate, not a biological macromolecule. No endogenous biological role is associated with ethyl 4-(4-hydroxybutyl)benzoate.

• Item-specific data: None provided; not intended for biological function assays (Research use only).

• General considerations (literature)

  • Aromatic esters with terminal alcohols are sometimes used as linkers or pro-moieties in biochemical probe synthesis; any biological activity arises from the final constructs, not from this intermediate itself.
  • Hydrolysis (enzymatic/chemical) could, in principle, release 4-(4-hydroxybutyl)benzoic acid or ethanol; rates depend on enzyme presence and environment, but no data are provided for this specific compound.

No medical or clinical claims are made; compound is offered strictly for laboratory research use.

Buffer Applications

Not typically applicable. Ethyl 4-(4-hydroxybutyl)benzoate is a hydrophobic organic intermediate and is not used as a buffering agent.

• If aqueous compatibility is required (e.g., bioconjugation), convert the ester to the corresponding acid and then to an active ester; conduct reactions in mixed aqueous/organic systems buffered by standard buffers (e.g., phosphate, HEPES) as appropriate for the biomolecule. This product itself does not define a buffer system.

Green Alternatives

• Solvent and reagent choices (general guidance)

  • Prefer greener solvents where feasible: EtOAc, 2-MeTHF, CPME, or propylene carbonate (PC) instead of DCM/DMF where reaction compatibility allows.
  • Carbonate/carbamate formation: use dimethyl carbonate or diethyl carbonate as both reagent and solvent when compatible (safer than phosgene-derived reagents).
  • Oxidations: choose catalytic TEMPO/air with benign co-oxidants (NaOCl/NaClO2) in biphasic systems; or O2 with nitroxyl catalysts instead of stoichiometric Cr(VI).

• Comparative overview (literature-based)

  • DCM vs EtOAc: EtOAc offers lower toxicity and better EHS profile; however, DCM can solubilize broader substrates and enables low-temperature control.
  • DMF/NMP vs Cyrene/PolarClean/PC: bio-based or low-toxicity dipolar aprotics reduce worker exposure; verify solubility and base stability.
  • THF vs 2-MeTHF/CPME: 2-MeTHF and CPME have lower peroxide hazard accumulation rates and improved water separations; reaction rates may differ.

• Waste minimization

  • Telescoping: perform alcohol activation followed by nucleophilic substitution without isolation when purity requirements permit.
  • Catalysis: DMAP or organic bases at low loadings for acylations; enzymatic transesterifications (lipases) under solvent-free or green solvent conditions.

• Energy efficiency

  • Microwave or flow platforms can reduce reaction times and solvent volumes; ensure thermal stability of the ester under process conditions.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item; it is supplied for research use only.

• Item-specific facts

  • Regulatory/compendial listings: Not specified for this item; refer to CoA/Spec Sheet.

• General formulation context (non-clinical)

  • As a synthetic intermediate, it may serve in the preparation of research-grade pro-moieties, linkers, or polymer conjugates. Any application in dosage forms would require separate qualification and is outside the scope of this listing.

No therapeutic or clinical claims are made.

Physical Properties

• Item-specific facts (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.

• Literature/computed (reference, not item specifications)

  • Molecular formula: C13H18O3 (derived from structure)
  • Molecular weight: ~222.28 g/mol (computed)
  • Predicted polarity: amphiphilic; aromatic ester plus terminal alcohol; expected moderate hydrophobicity with some hydrogen-bonding via –OH
  • Expected solubility profile (qualitative):
    • Good solubility in polar aprotic and moderately polar organic solvents (e.g., EtOAc, acetone, MeCN, DMSO)
    • Miscible with alcohols (MeOH, EtOH, i-PrOH)
    • Limited solubility in water due to hydrophobic aryl/alkyl content, partially offset by terminal –OH
  • LogP/logD: Not established; likely in the moderate range for aryl esters with one hydroxyl (literature expectation only)
  • Boiling point, melting point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• General notes for handling based on structure

  • The terminal –OH can engage in hydrogen bonding; material may be a low-viscosity oil or low-melting solid depending on crystal packing (actual state not specified).
  • Aromatic esters typically show π–π absorption near 200–230 nm; exact UV data not established for this item.

Quality and Grades

• Item-specific status

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

• How to interpret grades (general guidance)

  • Research/technical grade: suitable for most synthetic applications; trace impurities may be higher than in analytical grades.
  • High-purity/analytical (AR) grade: tighter control of organic/metal impurities; beneficial for sensitive catalysis or analytical work.
  • HPLC/LC-MS grade solvents/reagents: minimized UV-absorbing/background ions; pertinent if the reagent is used as a reference standard or in trace analysis sample prep.

• Impurity considerations for this class of compound (general)

  • Potential residuals: unreacted benzoate esters (ethyl benzoate), over-alkylated species, oxidation products of the alcohol, traces of solvent.
  • Water, peroxides, residual metals: Not specified for this item; refer to CoA/Spec Sheet.

• Recommendations

  • Request a recent CoA for assay, identity (NMR/GC/LC), and impurity profile aligned to your application (e.g., polymer synthesis vs. medicinal chemistry).
  • If using in moisture-sensitive steps (e.g., isocyanate coupling), verify Karl Fischer moisture on receipt (spec not provided by this listing).

Reaction and Applications

With a para‑benzoate ester and a terminal primary alcohol, this molecule is a versatile bifunctional synthon for linkers, polymers, and conjugates.

• Transformations at the terminal alcohol (literature/general)

  • Electrophile capture: tosylate/mesylate formation → subsequent SN2 to install azides, halides, or other nucleophiles (phase-transfer optional).
  • Carbonates and carbamates: reaction with chloroformates or isocyanates (DMAP or base catalysis) to give protective or functional linkers.
  • Etherification: Williamson conditions (alkoxide in DMF/DMSO) to introduce alkyl/benzyl groups; Mitsunobu enables inversion to form ethers with poor nucleophiles.
  • Oxidation: TEMPO/bleach or Swern/PCC to aldehyde → further to acid; careful to avoid ester cleavage.

• Transformations at the benzoate

  • Hydrolysis (saponification) to the corresponding 4-(4-hydroxybutyl)benzoic acid; then amide coupling (EDC/HOBt, HATU) or acid chloride formation.
  • Transesterification to tune the alcohol component (e.g., tert‑butyl for protection, benzyl for hydrogenolysis cleavage).
  • Activation: convert to acid (above) then to NHS ester or mixed anhydride for bioconjugation steps.

• Aryl ring manipulations (require prior functionalization)

  • Electrophilic substitution is deactivated by the para acyl-oxygen substituent; direct halogenation/nitration typically requires forcing conditions.
  • Directed metalation is feasible with appropriate protecting groups and bases.

• Use cases

  • Spacer/linker installation between aromatic cores and polar heads in materials.
  • Precursor for amphiphilic esters, surfactant-like probes, and pro-moieties in research compounds (non-clinical).

Reaction Conditions

The following are literature-style general conditions for common transformations of this motif; they are guidance only and not item specifications.

• Alcohol activation and substitution

  • Tosylation: p-TsCl (1.1–1.5 eq), base (pyridine or Et3N, 2–3 eq), DCM, 0 °C → rt, 1–4 h; typical isolated yields 75–95% for primary alcohols.
  • SN2 displacement of tosylate: NaN3, DMF, 60–90 °C, 4–16 h; halide or other nucleophiles analogous; yields 60–90% depending on nucleophile.

• Carbamate/carbonate formation

  • With isocyanates: catalytic DMAP (5–10 mol%), DCM or THF, rt to 40 °C, 2–12 h.
  • With chloroformates: base (DIPEA, 2 eq), DCM, 0 °C → rt; quench with aqueous NH4Cl.

• Oxidation of –CH2OH

  • TEMPO/NaOCl/NaBr, pH ~8.6 (buffered), 0–5 °C to rt; aldehyde in 70–90% typical yield; over-oxidation conditions furnish acid.
  • Swern (DMSO/(COCl)2, then Et3N), −78 °C → 0 °C.

• Benzoate manipulations

  • Hydrolysis (saponification): K2CO3 or NaOH (1–2 M) in MeOH/H2O or EtOH/H2O, 0–50 °C, 1–6 h → corresponding acid; acidification to isolate.
  • Transesterification: catalytic acid or base in ROH solvent, reflux; remove EtOH to drive equilibrium.

• Workup and purification

  • Typical quench to aqueous media, extraction with EtOAc/MTBE, brine wash, dry (Na2SO4), and silica gel chromatography (hexanes/EtOAc gradient). Protect –OH when necessary to avoid streaking.

Adjust conditions to the specific substrate and scale; monitor by TLC/GC/LC-MS.

Safety and Handling

• Item-specific hazard information (from Product Data)

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

• General safety guidance for aromatic esters with terminal alcohols (literature/general knowledge; not product-specific classification)

  • Likely to cause mild skin/eye irritation; avoid inhalation of vapors/aerosols and prolonged skin contact.
  • Use standard PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood when heating, concentrating, or aerosolizing.
  • Incompatibilities: strong oxidizers (may oxidize alcohol), strong bases/acids (can catalyze ester hydrolysis/transesterification), acylation/halogenating agents (reactive at –OH).
  • Fire safety: treat as combustible organic liquid/solid; keep away from ignition sources; store with flammables according to local practice.

• First-aid overview (always defer to SDS)

  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.

• Spill/leak response

  • Absorb with inert material (vermiculite/sand), collect in suitable container. Ventilate area and avoid environmental release.

Consult the product SDS for authoritative hazard classification and exposure limits.

Solvent Selection

Ethyl 4-(4-hydroxybutyl)benzoate is an amphiphilic organic intermediate. Solvent choice is driven by the reaction at either the terminal alcohol or the aryl ester.

• Polarity/miscibility (literature-based expectations)

  • Readily soluble in common organic solvents: DCM, THF, EtOAc, acetone, MeCN, toluene; miscible with alcohols (MeOH/EtOH/i-PrOH). Limited water solubility.

• Choosing a solvent by transformation

  • Alcohol functionalization (e.g., tosylation, carbonate formation): use dry DCM, THF, or MeCN with base (e.g., pyridine/DIPEA). Low temperatures aid selectivity.
  • Carbamate/urethane formation with isocyanates: anhydrous DCM/THF/toluene; catalytic DMAP often beneficial.
  • Ester hydrolysis or transesterification: MeOH/EtOH with acid/base catalyst; for selective alcohol reactions, avoid strong acid/base to protect the benzoate.
  • Metal-catalyzed couplings on the aryl ring (after appropriate activation): polar aprotic solvents (DMF, DMAc, NMP) or greener alternatives like Cyrene/PC.

• Small comparison (general)

  • THF: excellent miscibility and reactivity; peroxide-forming and requires drying.
  • EtOAc: greener, easy workup, good solubility; limited for strong nucleophiles.
  • MeCN: high polarity, good for SN1/SN2 and activations; toxic profile requires controls.
  • Toluene: good for high-temp operations; poor for ionic bases.

• Practical notes

  • Drying agents: 3 Å molecular sieves or distillation over CaH2 for acid-sensitive steps.
  • For analytical sample prep (LC/GC), choose solvents with suitable UV/volatility; avoid protic solvents when monitoring acylation kinetics.

Storage and Reconstitution

• Item-specific instructions (from Product Data)

  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance and reconstitution: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance for this class of compound

  • Store tightly sealed in an inert atmosphere (e.g., with desiccant) to limit moisture that can promote ester hydrolysis and to protect the free alcohol from oxidation.
  • If long-term storage is planned, consider amber glass to minimize light exposure; keep away from strong acids/bases and oxidizers.
  • If solidifies at lower temperatures, gently warm to ambient and swirl to homogenize before use; do not overheat. If supplied as an oil, no reconstitution is required.
  • For moisture- or air-sensitive transformations, dry prior to use (e.g., azeotrope with toluene or dry over 3 Å sieves) and handle under dry nitrogen/argon.

Always refer to the product’s CoA and SDS for definitive instructions.

Structure and Identity

Brief overview: Ethyl 4-(4-hydroxybutyl)benzoate is a para-substituted benzoate ester bearing a terminal primary alcohol via a four‑carbon tether; it functions as a bifunctional building block (aryl ester + aliphatic alcohol).

• Item-specific facts (from Product Data)

  • Product name: Ethyl 4-(4-hydroxybutyl)benzoate (SKU: E979191)
  • CAS: 85431-07-8
  • CID: 19907366
  • InChIKey: 61017 (as provided)
  • Storage: Room temperature
  • Research use: For research use only

• Literature/computed identifiers and descriptors (for reference only; not item specifications)

  • Typical molecular formula: C13H18O3 (literature/computed based on name)
  • Approx. molecular weight: ~222.28 g/mol (literature/computed)
  • Representative SMILES: O=C(OCC)c1ccc(CCCCO)cc1 (literature)
  • Functional groups: aromatic ring, benzoate ester (ethyl), primary alcohol (–CH2OH), flexible (CH2)4 spacer
  • 2D structural description: A benzene ring bearing at para positions (i) an ethyl benzoate group –C(=O)OCH2CH3 and (ii) a linear butyl chain terminating in –OH (–CH2–CH2–CH2–CH2–OH); no stereocenters.

• General chemistry notes

  • Bifunctional motif enables orthogonal derivatization at the alcohol (e.g., carbamates/ethers/carbonates) and at the ester (hydrolysis, transesterification, or amidation after activation).
  • Para substitution minimizes steric congestion around each handle, often improving reactivity in polymer and linker synthesis.

Synthetic Utility

• Functional handles and reactivity

  • Primary alcohol (–CH2OH): nucleophilicity allows acylation (esters, carbonates, carbamates), etherification (Williamson), and activation to sulfonates (Ms/Ts) for SN2 elaborations.
  • Benzoate ester: stable under many conditions but can be selectively hydrolyzed (acidic or basic), transesterified, or converted to the acid for amide coupling.

• Orthogonal strategy examples (literature/general)

  • Protect –OH as a tert‑butyldimethylsilyl (TBDMS) ether, then manipulate the benzoate (e.g., hydrolysis → amide coupling). Deprotect with TBAF to unveil the alcohol.
  • Activate –OH to a tosylate and perform intramolecular cyclizations or install terminal azide → CuAAC to introduce triazole linkers.
  • Oxidize –OH to aldehyde → Wittig/olefination or reductive amination (after hydrolysis to acid for bifunctional coupling).

• Retrosynthetic value

  • Serves as a para‑substituted aromatic core preloaded with a 4‑carbon spacer; simplifies access to families of para‑functionalized benzoates/benzamides with tunable hydrophilicity.

• Analytical characterization tips

  • 1H NMR: triplet for –CH3 of ethyl (≈1.2–1.3 ppm), quartet for –OCH2– (≈4.1–4.4 ppm), aromatic AA′BB′ pattern (≈7.0–8.1 ppm), and signals for –(CH2)4–OH (≈1.3–3.7 ppm; –CH2OH around 3.6–3.7 ppm). 13C NMR: ester carbonyl ≈165–173 ppm. IR: strong C=O ~1715–1735 cm−1, O–H broad ~3300–3500 cm−1 (if free).

Target Specificity

Not applicable. This product is a small-molecule organic intermediate and is not an antibody, enzyme, or biological targeting reagent.

• Item-specific targeting data: None provided.