4-(2-Phenylethoxy)benzaldehyde - Reagent grade

Cat. No.: P483195

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

사양 및 순도

Reagent grade

보관 조건

Room temperature

등급

Reagent Grade

Application Protocols

Not applicable. This SKU is a small-molecule building block and is not validated for bioassays such as WB, IHC, IF, or FC. For practical use, refer to the Reaction Conditions and Synthetic Utility sections for representative synthetic procedures involving aromatic aldehydes.

Biological Roles

This product is a synthetic aromatic aldehyde/aryl ether not typically associated with intrinsic biological roles.

• Endogenous function: None known; not a natural metabolite.
• Biochemical behavior (general): Aromatic aldehydes can form reversible adducts with nucleophiles (Schiff bases with amines, thiohemiacetals with thiols) under laboratory conditions; such reactivity underpins their use in bioconjugation chemistry research but is not a biological role.
• Research context: Para-aryloxybenzaldehydes are occasionally employed as scaffolds in medicinal chemistry discovery and as aldehyde handles for ligand or probe assembly. Any biological testing would be investigator-driven; no claims are made for in vivo relevance.

Item-specific biological activity, targets, or pathways: Not specified for this item.

Buffer Applications

Not typically applicable. 4-(2-Phenylethoxy)benzaldehyde is a neutral, hydrophobic organic building block and is not used to formulate aqueous buffer systems. For experimental work requiring this aldehyde in aqueous environments, employ co-solvents (e.g., DMSO, MeCN, EtOH) or emulsification strategies and refer instead to the Solvent Selection and Reaction & Applications sections.

Green Alternatives

Greener choices center on solvent and reagent selection rather than replacing the substrate itself.

• Greener solvent substitutions (general guidelines):
  • Replace DCM/chloroform in condensations with toluene, ethyl acetate, or 2-MeTHF when feasible.
  • Use ethanol or isopropanol as media for imine/oxime formation; drive equilibria by azeotropic removal of water or molecular sieves.
  • For olefinations (Wittig/HWE), consider MeCN, 2-MeTHF, or CPME instead of THF/DCM when compatible.

Comparison (general):

• DCM vs 2-MeTHF:

  • Environmental: 2-MeTHF (bio-based, better EHS profile) vs DCM (chlorinated, VOC with higher environmental burden).
  • Performance: Both dissolve aromatic aldehydes well; 2-MeTHF supports organometallic chemistry but has higher bp (difficult removal) and can contain peroxides (manage with testing/sieves).

• Toluene vs Acetone/EtOAc:

  • Toluene provides higher-temperature operation with good solvency; acetone/EtOAc are more benign but may participate in side reactions or offer lower solubility.

• Reagent choices:

  • Prefer catalytic hydrogenation or transfer hydrogenation over stoichiometric metal hydrides for reductions when compatible.
  • Use organocatalysts (e.g., secondary amines) for Knoevenagel/Michael cascades to reduce heavy-metal waste.

Note: Validate green substitutions at small scale to confirm kinetics/selectivity with this substrate’s electron-donating aryl ether substituent.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item. As an aromatic aldehyde, it is primarily used as a synthetic intermediate in research settings.

• Typical roles in pharma R&D (general):
  • Intermediate for structure–activity relationship (SAR) libraries via imine/oxime/hydrazone formation or olefination.
  • Handle for late-stage diversification (reductions, oxidations, acetalizations) when assembling candidate molecules.
• Regulatory status: Not specified; not supplied for human or veterinary use.
• Formulation relevance: Not commonly used as a formulation excipient; aldehydes are generally chemically reactive and avoided in finished dosage forms unless fully transformed.

Research Use Note (item-specific): For research use only.

Physical Properties

Only limited item-specific physicochemical specifications are provided for this SKU.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point, melting point, density, refractive index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (literature): 226.27 g/mol (for C15H14O2)
• Physical state and solubility profile (general/literature-based):
  • Expected to be a low-melting solid or high-boiling liquid depending on crystal habit; many para-aryloxybenzaldehydes are oils at ambient conditions.
  • Good solubility in common organic solvents: dichloromethane, chloroform, toluene, THF, diethyl ether, ethyl acetate, acetone, acetonitrile (general expectation for neutral diaryl ethers and aryl aldehydes).
  • Very low solubility in water.
• Partitioning (general): Aromatic aldehydes bearing diaryl ether frameworks are typically hydrophobic with moderate-to-high logP; specific logP for this item is not specified.
• UV characteristics (general): Aromatic π→π* bands expected near 200–280 nm with an n→π* shoulder for the aldehyde; item-specific UV cutoff not specified.

Note: For exact, item-specific values (mp/bp, density, water content, peroxide levels, UV cutoff), consult the product CoA/Spec Sheet.

Quality and Grades

• Supplied grade: Reagent Grade (item-specific). Reagent Grade generally indicates suitability for routine laboratory synthesis and analytical sample preparation where ultra-trace impurity control (e.g., LC/GC baseline, metal ppb) is not critical.
• What Reagent Grade implies (general):
  • Reasonable control of organic/volatile impurities for synthetic use.
  • Not specifically optimized for chromatographic baselines (vs. HPLC grade solvents) or trace-metal-sensitive catalysis (vs. trace-metal screened materials).
• Purity: Not specified for this item; refer to CoA/Spec Sheet for assay method and limits (e.g., GC, HPLC).
• Stabilizers/inhibitors: None indicated in the Product Data; if present for a particular lot, it will be disclosed on the CoA.
• Typical quality checks (general for aromatic aldehydes): Identity (1H/13C NMR, IR ν(C=O) ~1690–1720 cm−1), purity by GC/HPLC, residual solvents, water by Karl Fischer where applicable. Aldehyde value may be assessed by derivatization (e.g., 2,4-DNPH) in some workflows.
• Lot-to-lot considerations: Aldehyde content can decrease over long storage via oxidation; CoA date and retest intervals should be observed.

Reaction and Applications

As a para-aryloxy-substituted aromatic aldehyde, 4-(2-Phenylethoxy)benzaldehyde is a versatile electrophile and synthon.

• Carbon–carbon bond formation:
  • Wittig/Horner–Wadsworth–Emmons olefinations (E/Z control via ylide/phosphonate choice) to access para-aryloxy-stilbenes and cinnamates (literature generality).
  • Knoevenagel condensations with active methylene compounds (malonates, cyanoacetates) under base or amine catalysis to form substituted benzylidenes.
  • Aldol-type and Henry reactions with appropriate partners; note that aryl aldehydes lack enolizable α-H and act only as electrophiles.
• Nucleophilic additions/reductions:
  • NaBH4/DIBAL/LAH reductions to the corresponding benzyl alcohol (literature), or catalytic hydrogenation to alcohol.
  • Cyanohydrin and bisulfite adduct formation for purification/derivatization.
• Heteroatom derivatizations:
  • Imine, oxime, hydrazone formation for ligand scaffolds and crystallizable derivatives.
  • Acetal protection (dimethyl acetal, 1,3-dioxolanes) to mask the aldehyde during multi-step sequences; deprotect under acidic aqueous conditions.
• Transformations leveraging the ether:
  • Selective O-dealkylation (e.g., BBr3, BCl3, or AlCl3 conditions; literature) to regenerate p-hydroxybenzaldehyde while retaining the aldehyde.
  • Benzylic functionalization on the phenethyl arm (radical bromination, oxidation to ketone/acid) without engaging the aldehyde if protected.
• Applications (manufacturer text expansion): Useful as a substituted benzaldehyde building block for constructing diaryl frameworks, Schiff bases/ligands, and conjugated systems in materials and organic synthesis research.

Reaction Conditions

Representative literature-style conditions for transformations of aryl aldehydes like 4-(2-Phenylethoxy)benzaldehyde (guidance; optimize per application):

• Imine (Schiff base) formation:
  • Solvent: EtOH, iPrOH, toluene, or MeCN.
  • Catalyst: AcOH (0.1–1 equiv) or molecular sieves (3Å/4Å) to remove water.
  • Temperature/time: RT to reflux; 1–16 h depending on amine/basicity.
  • Notes: Use Dean–Stark in toluene for water removal; monitor by IR (loss of aldehyde C=O ~1700 cm−1) and NMR.
• Oxime/hydrazone formation:
  • Solvent: EtOH/MeOH or MeCN; pyridine can accelerate with hydroxylamine.
  • Conditions: RT to 60 °C, 1–6 h.
• Wittig olefination:
  • Solvent: THF, DCM, toluene.
  • Base: n-BuLi/NaHMDS for ylide generation (stabilized or semi-stabilized ylides as required).
  • Temperature: −78 °C to RT; 1–4 h after addition.
  • Notes: Dry, oxygen-free conditions; aldehyde protection unnecessary if handled cold and under inert atmosphere.
• HWE (phosphonate) olefination:
  • Base: NaH, K2CO3, DBU; solvent MeCN/THF.
  • Temperature: 0 °C to RT; E-selective with stabilized phosphonates.
• Reduction to benzyl alcohol:
  • NaBH4 in MeOH/EtOH (0 °C to RT) or catalytic hydrogenation (Pd/C, H2, RT–50 °C).
  • Chemoselectivity: Ether remains intact; avoid over-reduction of any unsaturation formed upstream.
• Protective acetalization:
  • Reagents: MeOH (cat. HCl) for dimethyl acetal or ethylene glycol with p-TsOH for 1,3-dioxolane.
  • Conditions: Dean–Stark/toluene or azeotropic removal of MeOH/H2O.

All values are general literature guidance, not item-specific specifications.

Safety and Handling

• GHS classification, signal word, pictograms, H-statements (item-specific): Not specified for this item; refer to the SDS for authoritative safety data.
• General hazards (class-based, literature): Aromatic aldehydes are typically skin/eye irritants and may cause respiratory irritation. Avoid inhalation/ingestion and prolonged skin contact. The aldehyde functional group can sensitize some individuals; handle with care.
• PPE: Use safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Employ a fume hood for weighing and transfers to minimize vapor/aerosol exposure.
• Incompatibilities: Strong oxidizers (risk of over-oxidation to the corresponding acid), strong bases (possible Cannizzaro-type reactions under concentrated base), strong reducing agents (reduction to benzyl alcohol). Avoid reactive metals in the presence of moisture.
• Stability considerations: Aryl ethers are generally resistant to peroxide formation; the aldehyde can slowly oxidize on air/light exposure. Minimize headspace oxygen and store tightly closed. Use antioxidants/inert gas blanket if long-term storage is anticipated (general best practice).
• First-aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill response: Absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry to drains.

Solvent Selection

This compound is a neutral, moderately lipophilic aromatic aldehyde/aryl ether. It dissolves well in many organic solvents used for synthesis and purification.

• Polarity/miscibility (general guidance):
  • Highly soluble: dichloromethane (DCM), chloroform, toluene, THF, ethyl acetate, acetone, acetonitrile, diethyl ether.
  • Poorly soluble: water and highly protic, very polar aqueous media.
• Choosing a solvent by operation:
  • Nucleophilic additions/condensations (e.g., imine, Wittig, Henry): DCM, toluene, THF, or MeCN are commonly effective. For base-sensitive protocols, use non-protic, aprotic solvents.
  • Oxime/hydrazone formation and purifications: EtOH/MeOH mixtures or MeCN/DCM with catalytic acid/base as needed.
  • Chromatography: Elutes in low-to-mid polarity solvent systems (hexanes/EtOAc, toluene/EtOAc). Aldehyde polarity increases with formation of hydrates/adducts; maintain dry eluents.
• Small comparison (general):
  • DCM: excellent solubility, fast evaporation; not green.
  • Toluene: good solubility, higher bp suits elevated-temperature condensations; more benign than chlorinated solvents.
  • THF/2-MeTHF: good for organometallic additions; water-miscible (THF) vs partially (2-MeTHF).
• Drying: For moisture-sensitive reactions (e.g., Wittig), dry solvents (molecular sieves, solvent systems) improve selectivity and suppress aldehyde hydrate formation.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature.
• Container: Tightly closed, moisture-free container with minimal headspace. Amber glass recommended to limit light exposure that can promote oxidation.
• Atmosphere: Although not required, storing under inert gas (N2/Ar) is good practice for aldehydes to limit aerial oxidation to the corresponding acid (general guidance).
• Stabilization: No stabilizer specified for this item; refer to CoA if any inhibitor is used. If prolonged storage is expected, consider keeping a small working aliquot and the main stock sealed.
• Reconstitution/working solutions:
  • Solvents: Prepare solutions in dry organic solvents (DCM, toluene, THF, EtOAc, MeCN, alcohols) as required by the application.
  • Concentrations: Choose based on downstream reaction stoichiometry; no item-specific limits are provided.
  • Shelf-life of solutions: Aldehyde solutions may slowly oxidize; prepare fresh or store short-term at 2–8 °C under inert atmosphere.
• Shipping: Not specified for this item; consult the SDS for transport classifications if needed.
• Research Use Note (item-specific): For research use only.

Structure and Identity

A para-substituted aromatic aldehyde featuring an aryl ether linkage to a 2-phenethyl moiety; useful as an electrophilic building block with a para-directing, weakly donating ether substituent.

• Item-specific registry data (CAS, CID, InChIKey, SMILES): Not specified for this item; refer to CoA/Spec Sheet.
• Preferred name: 4-(2-Phenylethoxy)benzaldehyde (p-(2-phenylethoxy)benzaldehyde)
• Molecular formula (literature): C15H14O2
• Molecular weight (literature): 226.27 g/mol
• Suggested SMILES (literature): O=CC1=CC=C(OCCc2ccccc2)C=C1
• InChIKey (literature): Not specified in provided data.
• Structural features:
  • Two benzene rings: one bearing an aldehyde (–CHO) and an ether substituent in para relationship; the second ring is part of a 2-phenethyl chain (–O–CH2–CH2–Ph).
  • Functional groups: aromatic aldehyde (electrophilic carbonyl), aryl ether (electron-donating via resonance to the aldehyde ring), benzylic methylenes.
  • 2D description: A para-formyl phenyl ring connected through an oxygen to an ethylene spacer terminating in a phenyl ring (Ar–O–CH2–CH2–Ar′), with –CHO para to –O– on the first ring.
• Stereochemistry: None (achiral, no stereocenters).

Synthetic Utility

Key functional elements make this compound a flexible synthon:

• Aldehyde (–CHO):
  • Electrophile for C–C bond formation (Wittig/HWE, Knoevenagel, Henry, Strecker-type additions with suitable partners).
  • Readily derivatized to oximes/hydrazones/Schiff bases for ligand scaffolds or purification handles; reversible under controlled conditions.
  • Chemoselective transformations: reduction to benzyl alcohols (NaBH4, catalytic hydrogenation) or oxidation to acids (e.g., Pinnick) or nitriles via oxime dehydration.
• Aryl ether (Ar–O–CH2–CH2–Ph):
  • Electron-donating into the formyl-bearing ring, modulating reactivity and directing electrophilic aromatic substitution para/ortho (aldehyde is meta-directing but overridden by protection strategies).
  • Amenable to O-dealkylation (BBr3/BCl3) to unveil p-hydroxybenzaldehyde, enabling divergent synthesis.
  • Benzylic CH2 sites allow radical bromination/oxidation to elaborate side chains.
• Retrosynthetic value:
  • Accessible from p-hydroxybenzaldehyde and a 2-phenethyl electrophile (e.g., 2-phenethyl bromide) via Williamson ether synthesis; orthogonal protection of the aldehyde (as acetal) simplifies etherification.
• Materials/ligand routes:
  • Formation of conjugated diaryl alkenes and donor–acceptor systems after olefination; Schiff bases serve as N,O-ligands for coordination chemistry (research context).

Target Specificity

Not applicable. This product is a small-molecule organic reagent and does not possess biological target specificity, epitope recognition, or immunochemical properties. No antibody/biomolecule attributes are associated with this SKU.

자주 묻는 질문

What does Reagent Grade mean?

Reagent Grade is a defined analytical purity tier suitable for general analytical and reagent applications. It specifies a minimum assay percentage, controlled limits on common impurities (water, heavy metals, residue on ignition), and lot-to-lot consistency. Reagent Grade is one of several purity tiers — choose based on the sensitivity and regulatory requirements of your method.

How should this product be stored?

Store at room temperature.

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.