4-Ethoxybenzonitrile - 10mM in DMSO , CAS No.25117-74-2

CAS: 25117-74-2 Cat. No.: E660982 분자식: C₉H₉NO 분자량: 147.18 EC 번호: 623-638-7

GRADE & PURITY 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

사양 및 순도

10mM in DMSO

보관 조건

Store at -80°C

배송

Dry ice packs + Cold packs

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이름과 식별자

이성체 SMILES

CCOC1=CC=C(C=C1)C#N

분자량

147.18

Reaxy-Rn

2613602

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2613602&ln=

화학 및 물리적 특성

• 끓는점(°C): 145°C/18mmHg(lit.)
• 녹는점(°C): 60-64°C

Application Protocols

No application protocols are specified for this item. This product is a general synthetic building block; procedures depend on the transformation of interest (e.g., hydrolysis, reduction, metalation, or coupling).

• For reaction set-up, consult the “Reaction Conditions” tab for general literature conditions and adapt to your scale and equipment.
• For analytical monitoring, TLC (UV-active), HPLC/GC, and 1H/13C NMR are typically effective. The nitrile group shows a characteristic IR band near ~2220–2260 cm−1 (literature; method development aid).

Biological Roles

• Item-specific biological data: Not specified for this item; no biological testing is claimed. For research use only.

• General context (literature):

  • 4-Ethoxybenzonitrile is a synthetic aromatic nitrile without known endogenous biological role.
  • Aryl nitriles occur in various bioactive small molecules (e.g., agrochemicals and medicinal chemistry scaffolds) where the CN group can modulate lipophilicity, metabolic stability, and serve as a polar, weakly hydrogen-bond-accepting handle.
  • The para-ethoxy substituent can influence membrane permeability and binding through electronic donation and increased hydrophobic surface area.

• Biotransformation (general):

  • In biological systems and environmental contexts, nitriles can be hydrolyzed by nitrilases/nitrile hydratases to amides/acids; rates are highly substrate- and organism-dependent. No specific data are provided for this compound.

Buffer Applications

This compound is a neutral, hydrophobic organic building block and is not used as a buffering agent. It has no defined acid/base pair for buffering in the physiological pH range.

• If needed in biochemical assays, prepare stock solutions in miscible organic co-solvents (e.g., DMSO, ethanol, MeCN) and dilute into the assay buffer within tolerated solvent limits.
• For buffering needs, select dedicated buffers (e.g., phosphate, HEPES, TRIS) appropriate to your pH range.

Green Alternatives

• Solvent-level improvements (general guidance for work with aryl nitriles):

  • Replace THF/Et2O with 2-MeTHF or CPME in reductions (DIBAL-H, BH3) and metalations where compatible; both offer improved safety and renewability.
  • Use ethanol or isopropanol as recrystallization solvents when possible instead of chlorinated solvents.
  • For polar reactions (hydrolysis, substitutions), consider propylene carbonate or γ-butyrolactone instead of DMF/NMP where catalyst/base compatibility permits.

• Energy and process considerations:

  • Favor catalytic hydrogenation over stoichiometric metal hydrides when feasible to minimize waste; use supported catalysts and continuous flow to improve safety.
  • Conduct hydrolyses under microwave or flow conditions to reduce time and energy inputs.

• Comparison snapshot (general):

  • THF vs 2-MeTHF: similar solvating power; 2-MeTHF is bio-derived, forms fewer peroxides, and simplifies phase separations due to hydrophobicity.
  • DCM vs EtOAc: EtOAc is less toxic and has a better environmental profile; if solubility allows, prefer EtOAc for extractions and chromatography.
  • DMF/NMP vs Cyclic carbonates (PC): PC is safer and higher boiling; check base stability and workup protocols.

• Reagent choices:

  • Choose aqueous hydrogen peroxide/oxygen catalytic oxidations over Cr(VI) oxidants when converting derived amines/alcohols in downstream steps.

Note: These are general sustainability strategies; verify applicability to your specific transformation and substrate set.

Pharmaceutical Uses

• Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet. No claim is made that this material meets any compendial monograph.

• General role (literature/industry practice):

  • 4-Ethoxybenzonitrile can serve as a chemical intermediate in API and agrochemical synthesis where a para-ethoxy phenyl motif is required.
  • It is not used as an excipient; rather, it is a synthetic building block that can be transformed into acids, amides, aldehydes, or amines for further elaboration.
  • For GMP manufacturing, route-specific impurity profiles (residual solvents, hydrolysis products, metal residues) must be controlled; process development typically defines specifications tighter than research grade.

• Analytical controls typically applied (general):

  • Identity by NMR/IR/MS; assay by HPLC/GC; limits on related aromatics and hydrolysis products; residual solvent by GC-HS; water by Karl Fischer;, and where relevant, elemental impurities by ICP-MS per ICH Q3D.

• Handling in development settings:

  • Prepare solutions in suitable solvents for throughput screening; confirm stability under storage and processing conditions (light, heat, pH). No clinical claims are made.

Physical Properties

• Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general values (for reference only; not product specifications):

  • Physical state: typically a crystalline solid or low-melting solid for many p-alkoxy benzonitriles (literature trend).
  • Appearance color: often off-white to pale solid (literature observation for related compounds).
  • Solubility: expected to be sparingly soluble in water; soluble in common organic solvents such as ethanol, methanol, acetone, acetonitrile, THF, DCM, toluene, and ethyl acetate (literature/general for aryl nitriles and aryl ethers).
  • Polarity/logP: aromatic nitriles with para-alkoxy substituents generally show moderate lipophilicity with enhanced polarity relative to anisoles (literature rationale). Specific logP not specified for this item.
  • Boiling/melting point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Practical handling notes (general):

  • The nitrile chromophore absorbs in the deep UV; for HPLC detection, 210–230 nm is commonly responsive (general analytical guidance). Verify with your method.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• What grade implies (general guidance):

  • Research- or synthesis-grade aryl nitriles are typically controlled for assay/purity by GC/HPLC and 1H NMR, with limits on related aromatics, residual solvents, and hydrolysis products (amide/acid).
  • For chromatography-sensitive work (photo- or electrochemistry, bioassays), low UV-absorbing impurities and low metal content may be important. If you require HPLC- or LC–MS-grade material, request the appropriate specification.

• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Aryl nitriles generally do not require added stabilizers; product is typically offered neat.

• Trace analyses often requested (general):

  • Water (KF), residual solvents, assay by quantitative NMR or GC, and identity confirmation by MS. If these are critical to your use, request the batch CoA prior to ordering.

Reaction and Applications

• As a functionalized aryl nitrile, 4-ethoxybenzonitrile serves as a versatile intermediate in synthesis of para-ethoxy–substituted benzenes and benzo-fused frameworks.

• Representative application families (literature/general):

  • Nitrile transformations:
    • Hydrolysis to amide (–CONH2) or acid (–CO2H) under acidic or basic conditions; amide can be further elaborated (e.g., coupling to give anilides).
    • Reductions: DIBAL-H to the corresponding aldehyde; LiAlH4/BH3 to p-ethoxybenzylamine; catalytic hydrogenation (Raney Ni/Pd) also feasible.
  • Directed ortho-metalation (DoM): The nitrile is a strong ortho-director; with strong bases (s-BuLi, LDA) at cryogenic temperatures, ortho-lithiated species can be trapped with electrophiles to access densely substituted patterns.
  • Cross-coupling via C–CN activation: Ni- or Pd-catalyzed coupling of aryl nitriles enables aryl–aryl and aryl–alkyl bond formation after CN activation; suitable ligands (e.g., bulky NHCs or phosphines) are often required.
  • Nucleophilic aromatic substitution (SNAr): The para-ethoxy reduces ring activation relative to nitro; however, the nitrile still withdraws and can facilitate SNAr at positions ortho to CN in appropriately substituted systems.
  • Electrophilic aromatic substitution: The net directing effect is mixed (ethoxy donates, nitrile withdraws); conditions can be tuned to functionalize positions influenced by the stronger directing group and sterics.

• Use-cases:

  • Intermediate toward p-ethoxybenzoic acid/amide, p-ethoxybenzaldehyde, and p-ethoxybenzylamine.
  • Precursor for dye, liquid-crystal, and agrochemical motifs where para-alkoxy/para-cyano substitution patterns are common.

Reaction Conditions

General literature guidance below; verify on small scale and optimize for your substrate/catalyst system.

• Hydrolysis of nitrile:

  • Acidic: 6 M HCl or H2SO4, 80–120 °C, hours to overnight → amide/acid depending on conditions; aqueous ethanol can aid solubility.
  • Basic: KOH/NaOH (2–6 equiv) in EtOH/H2O or DMSO/H2O, reflux → amide (shorter) or acid (longer, stronger base). Work up by acidification.

• Reduction:

  • To aldehyde: DIBAL-H (1.2–1.5 equiv) in toluene/THF at −78 to −20 °C, then mild aqueous workup → p-ethoxybenzaldehyde (literature precedent for aryl nitriles).
  • To amine: LiAlH4 (2–4 equiv) in THF/Et2O, 0 °C to reflux, 2–16 h; or BH3·THF (3–6 equiv) in THF, reflux; or catalytic hydrogenation (Pd/C, H2 1–5 bar) in EtOH.

• Directed ortho-lithiation (DoM):

  • s-BuLi (1.1–1.5 equiv) ± TMEDA in THF or Et2O at −78 °C, 0.5–2 h; trap with electrophiles (CO2, I2, B(OMe)3, DMF). Strict anhydrous/inert conditions required.

• C–CN activation/cross-coupling (decyanative or direct coupling):

  • Ni(cod)2 (5–10 mol%) with bulky phosphines or NHC ligands in THF/dioxane, 60–120 °C; partner- and ligand-dependent. Decyanative borylation/arylation conditions are common in literature.

• O-dealkylation to phenol:

  • BBr3 (1–3 equiv) in DCM at −78 to 0 °C, then warm to rt, hours → p-hydroxybenzonitrile. Alternative: HBr/AcOH under reflux.

• Typical workup/purification:

  • Quench carefully (exotherm control), aqueous separations, charcoal treatment if needed, and purification by crystallization or flash chromatography (EtOAc/hexanes or toluene mixtures).

Safety and Handling

• Item-specific GHS details: Not specified for this item; refer to SDS for authoritative classification.

• General hazards for aromatic nitriles and aryl ethers (literature/general):

  • May cause irritation to skin, eyes, and respiratory tract upon contact or inhalation of dust.
  • Combustible organic solid; avoid ignition sources and excessive dusting.
  • Nitriles can hydrolyze under strongly acidic or basic conditions to amides/acids; avoid incompatible reagents unless intended.

• Recommended PPE and engineering controls (good laboratory practice):

  • Wear lab coat, nitrile gloves, and splash-rated safety goggles.
  • Handle powders in a fume hood; avoid inhalation of dust/particles.
  • Use antistatic precautions when weighing dry solids.

• Storage incompatibilities (general):

  • Keep away from strong oxidizers, strong acids/bases (to prevent hydrolysis), and strong reducing agents (to prevent unintended nitrile reduction).

• First-aid overview (general; 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; obtain medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• SDS: Consult the product-specific SDS for GHS pictograms, signal word, H/P statements, and emergency measures.

Solvent Selection

• Polarity/miscibility profile (general for aryl nitriles):

  • Moderately polar, aprotic aromatic compound; excellent solubility in ethers (THF, 2-MeTHF), chlorinated solvents (DCM, chloroform), esters (EtOAc), ketones (acetone, MEK), aromatics (toluene), and nitriles (MeCN). Poor aqueous solubility.

• Practical choices by task:

  • Nucleophilic substitutions/hydrolysis on the nitrile: polar aprotic solvents (DMF, DMSO, MeCN) increase rate; for acid/base hydrolysis, aqueous alcohols or biphasic setups can be used.
  • Reductions (DIBAL-H to aldehyde; LiAlH4/BH3 to amine): anhydrous ethereal solvents (Et2O, THF, CPME, 2-MeTHF) under inert atmosphere are standard.
  • Metalation (directed ortho-lithiation): anhydrous THF or Et2O at low temperature (≤ −78 °C) with bases like s-BuLi; quench into electrophiles.
  • Cross-coupling/decynation via C–CN activation: polar ethers (THF/2-MeTHF) or high-boiling polar aprotics (dioxane, DMF) depending on catalyst system.

• When to choose alternatives:

  • If low-boiling, greener media are desired, consider 2-MeTHF or CPME instead of THF/Et2O; for high polarity needs, consider propylene carbonate or GBL over DMF where compatible.

• Small comparison (general):

  • THF: excellent solubility, easy removal, peroxide risk; 2-MeTHF: greener, hydrophobic, similar performance; MeCN: enhances polar reactions but higher toxicity; Toluene: good for thermal stability but lower polarity.

Storage and Reconstitution

• Item-specific storage and shipping (Product Data):

  • Storage Conditions: Store at −80 °C.
  • Shipped In: Dry ice packs + Cold packs.

• General storage guidance (complementary):

  • Keep container tightly closed in a dry, inert atmosphere (nitrogen/argon) to minimize moisture ingress and oxidative degradation of trace impurities.
  • Protect from prolonged light and heat. If frequent access is needed, consider aliquoting to minimize freeze–thaw and headspace exposure.

• Solution handling (general):

  • Prepare stock solutions in dry organic solvents (e.g., DMSO, MeCN, THF, toluene, EtOAc) as appropriate for your application. Filter if necessary through a 0.2 µm PTFE membrane.
  • For long-term solution storage, keep under inert gas at low temperature (e.g., −20 to −80 °C) and protect from light. Verify stability by periodic analytical checks (HPLC/NMR).

• Reconstitution: Not applicable to this neat solid; dissolve to desired concentration in a compatible anhydrous solvent immediately before use.

• Disposal: Follow institutional and local regulations for disposal of organic nitriles and halogen-free aromatic wastes.

Structure and Identity

Brief description: 4-Ethoxybenzonitrile is a para-ethoxy–substituted aromatic nitrile, useful as an electron-poor anisole analog and versatile aryl–CN building block.

• Item-specific (Product Data):

  • SKU: E660982
  • Product Name: 4-Ethoxybenzonitrile
  • CAS: 25117-74-2
  • Storage Conditions: Store at -80°C (per Product Data)
  • Shipped In: Dry ice packs + Cold packs (per Product Data)
  • Research Use Note: For research use only

• Literature/computed identity (not item-specific; for reference):

  • Synonyms: p-Ethoxybenzonitrile; 4-ethoxybenzenecarbonitrile
  • Molecular formula: C9H9NO (literature)
  • Molecular weight: 147.17 g/mol (literature)
  • Canonical SMILES: CCOc1ccc(cc1)C#N (literature)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general description):

  • Aromatic benzene ring bearing two para-disposed substituents: an electron-donating ethoxy group (–OCH2CH3) and a strongly electron-withdrawing nitrile (–C≡N).
  • Functional groups: aryl ether (Ar–O–Et), nitrile (sp-hybridized C≡N).
  • Conjugation: the nitrile is conjugated to the arene, lowering ring electron density; the ethoxy donates by resonance/induction.
  • 2D description: A six-membered phenyl ring with –OC2H5 at the para position relative to –C≡N. No stereocenters; planar aromatic core with linear C≡N.

Synthetic Utility

• Functional-group handles:

  • Nitrile (–C≡N): convertible to aldehyde (DIBAL-H), primary amine (LiAlH4, BH3, catalytic hydrogenation), amide/acid (acidic/basic hydrolysis), tetrazoles (via [3+2] with azide after imidoyl chloride formation), and can direct ortho-metalation.
  • Para-ethoxy aryl ether: modulates electronics and solubility; can be cleaved to phenol under strong Lewis/Brønsted acidic conditions (e.g., BBr3/BCl3 or HBr/AcOH for dealkylation), enabling access to p-hydroxybenzonitrile derivatives.

• Strategic roles in synthesis (literature/general):

  • DoM platform: ortho-lithiation adjacent to CN followed by quench with electrophiles (carbonyls, halogens, borylation agents) to build densely substituted arenes.
  • Cross-coupling via C–CN activation: Ni catalysts with bulky ligands can convert the aryl–CN bond to C–C or C–B bonds, expanding diversification options from a nitrile starting point.
  • Electrophile introduction on the benzyl position after nitrile reduction to amine/aldehyde, enabling routes to p-ethoxybenzyl derivatives.
  • CW (convergent) approaches: use as masked carbonyl equivalent; the nitrile can be unveiled to carboxylic acid late-stage to install amide/ester linkages.

• Retrosynthetic value:

  • Provides a para-alkoxy/para-cyano pattern that’s challenging to access directly by electrophilic substitution; starting from this scaffold enables orthogonal diversification (O-dealkylation, nitrile conversion, ortho-functionalization).

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, probe, or biologic. No antigen/epitope, clone, isotype, or species reactivity is associated.

• Item-specific bioassay targets: Not specified for this item.