3-(3,3-Diethoxypropoxy)benzonitrile - ≥95% , CAS No.1394041-76-9

CAS: 1394041-76-9 Cat. No.: D1253771 Formula: C₁₄H₁₉NO₃ Peso molecolare: 249.3

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

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

IUPAC Name

3-(3,3-diethoxypropoxy)benzonitrile

InChIKey

LTHHZLOHKGENKX-UHFFFAOYSA-N

INCHI

1S/C14H19NO3/c1-3-16-14(17-4-2)8-9-18-13-7-5-6-12(10-13)11-15/h5-7,10,14H,3-4,8-9H2,1-2H3

Peso molecolare

249.3

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Benzonitriles Alkyl aryl ethers Nitriles Acetals Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Benzonitrile - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Acetal - Ether - Carbonitrile - Nitrile - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Cyanide - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 249.300 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 249.136 Da
• Monoisotopic Mass: 249.136 Da
• Topological Polar Surface Area: 51.500 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 255.000
• 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. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

This product is intended for research and synthetic applications and is not a biological metabolite or ligand of established physiological relevance.

• General considerations

  • Aromatic nitriles and acetals are not typical endogenous biomolecules. Any biological activity would be structure‑dependent and requires dedicated study.
  • If used as a probe precursor, the nitrile can be transformed into amides/amines to access chemotypes with known bioactivity; however, such transformations and biological testing fall outside the scope of this product listing.

• Laboratory use only

  • Research Use Only, not for human or veterinary use (per Product Data). No claims of biological efficacy or safety are made.

For biological assays or target engagement studies, derivatives prepared from this intermediate should be evaluated under appropriate regulatory and institutional guidelines.

Buffer Applications

This compound is a neutral, hydrophobic organic intermediate and is not used as a buffering agent.

• Not typically applicable

  • It lacks acid–base functionality in the physiological pH range and is poorly soluble in water; therefore, it is unsuitable for preparing aqueous buffers or electrophoresis running solutions.

• Practical note

  • When handling in aqueous workflows (e.g., extractions), adjust pH only to protect the acetal from acid‑catalyzed hydrolysis; do not rely on this compound to contribute to buffering capacity.

Green Alternatives

While 3-(3,3-diethoxypropoxy)benzonitrile itself is a specialty intermediate, greener choices can be made in its handling and in route design.

• Solvent choices (comparison; general guidance)

  • 2‑MeTHF vs THF: 2‑MeTHF is biorenewable, has higher boiling point (facilitates reactions at reflux), and simplifies aqueous workups due to partial immiscibility; both solubilize aryl ethers well.
  • EtOAc vs DCM: Ethyl acetate offers lower toxicity and better environmental profile; suitable for extractions and chromatography, though DCM provides higher elution strength and lower viscosity.
  • Toluene vs chlorinated solvents: Toluene can replace DCM/chloroform in many steps with appropriate temperature control.

• Reagents/process

  • Use catalytic hydrogenation with supported catalysts in ethanol/2‑propanol as alternatives to stoichiometric metal hydrides for nitrile reductions, when compatible with the acetal.
  • Choose buffered or neutral workups to preserve the acetal and reduce acidic waste streams.
  • Consider flow hydrogenation to enhance safety and minimize solvent volumes.

• Waste minimization

  • Plan the sequence to avoid acetal cleavage/regeneration cycles; each cycle adds solvent and acidic aqueous waste.
  • Employ reusable scavengers or solid acids for final deprotection to reduce liquid waste.

• Energy and safety

  • Favor room‑temperature or mild‑reflux conditions in higher‑boiling green solvents (2‑MeTHF, CPME, toluene) to reduce chilling demands associated with cryogenic reagents when possible.

These suggestions are general/literature‑based; tailor to your process constraints and confirm compatibility with this substrate.

Pharmaceutical Uses

No pharmacopeial excipient status or formulation role is specified for this item.

• Item-specific statement

  • Pharmaceutical/Excipient status: Not specified for this item; refer to CoA/Spec Sheet.

• General context (non-clinical)

  • Aromatic nitriles are common intermediates in medicinal chemistry campaigns. The acetal moiety can serve as a masked aldehyde for library synthesis and late‑stage diversification.
  • If incorporated into drug discovery workflows, this material would typically be used upstream in synthesis, not as a finished dosage component.

• Compliance note

  • Research use only. No therapeutic claims are made or implied. Any use in GMP or clinical settings requires independent qualification and regulatory review beyond the scope of this product.

Physical Properties

Item-specific numerical specifications are not provided for this catalog entry.

• Item-specific specifications

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point, melting point, density, refractive index, water/peroxide/metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed expectations for closely related structures (context only; not product specs)

  • Aromatic nitrile ethers of comparable size are typically colorless to pale yellow liquids or low‑melting solids with moderate volatility.
  • The acetal segment (diethoxyacetal) increases lipophilicity and usually raises boiling point relative to simple anisole ethers; acetals commonly have refractive indices in the nD 1.44–1.50 range (literature, class trend).
  • Solubility profile (general): expected to be sparingly soluble in water and highly soluble in common organic solvents such as dichloromethane, ethyl acetate, THF, toluene, and acetonitrile (literature, class behavior for aryl ethers with acetal moieties).
  • Acid/base properties: acetals are generally neutral and hydrolytically stable under basic conditions but can hydrolyze under acidic, aqueous conditions (literature). The nitrile is a weakly basic/weakly polar moiety.

• Practical implications

  • Plan workups and chromatography with moderately nonpolar to mid‑polarity eluents (e.g., hexanes/EtOAc or toluene/EtOAc).
  • Avoid exposing to strong aqueous acids or prolonged silica contact under acidic conditions to minimize acetal hydrolysis.

Always consult the product’s CoA/SDS for definitive physical data.

Quality and Grades

• Item-specific grade/purity

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

• How to interpret common grades (general guidance)

  • Technical grade: suitable for many synthetic steps where trace impurities are tolerable.
  • Analytical/AR grade: tighter impurity limits suitable for quantitative analysis and impurity‑sensitive reactions.
  • HPLC grade/LC‑MS grade solvents: defined by low UV background and low nonvolatile residue; relevant when the compound is used as an analytical standard or in sample prep.
  • ≥98–99% purity: typically preferred for multistep synthesis to minimize impurity carryover; check residual solvent and water content on CoA.

• Considerations for this structure (general)

  • Acetal integrity can be compromised under acidic workup or during storage with acid residues; grades free of acidic stabilizers are advantageous.
  • Trace acids on silica can induce partial hydrolysis; for highest fidelity, verify by 1H NMR (diagnostic acetal methine and ethoxy resonances) and LC/HPLC purity before scale‑up.
  • If chiral impurities are a concern (not expected here), confirm by chiral HPLC; otherwise, standard achiral methods suffice.

• Documentation

  • For this SKU, rely on the batch CoA for actual assay, impurity profile, residual solvents, and recommended analytical methods. Where application‑critical, request a specification sheet defining purity thresholds aligned to your project.

Reaction and Applications

As a benzonitrile bearing an aryl ether tethered to a diethoxyacetal, this compound is a versatile intermediate and protecting‑group synthon.

• Transformations involving the nitrile (literature/general)

  • Reduction to primary amine (via catalytic hydrogenation, metal hydride, or borane; avoid acid that could cleave the acetal).
  • Partial reduction to imine/aldehyde equivalents (e.g., DIBAL‑H to aldehyde under carefully controlled low temperature; acetal survival depends on conditions).
  • Hydrolysis to amide or carboxylic acid under strongly acidic or basic aqueous conditions (note: acetal will hydrolyze under acid; protect accordingly or sequence steps).

• Transformations involving the acetal (literature/general)

  • Acid‑catalyzed deprotection to reveal a carbonyl (typically an aldehyde at the terminal position of the side chain), enabling intramolecular cyclizations or further elaboration.
  • Exchange (transacetalization) to tailor protecting group properties.

• Aryl ether as a linker (general)

  • The ether provides a robust, non‑basic spacer; under strong Lewis acids it may be cleaved, but generally it is stable to bases and many reductants.

• Representative application ideas

  • Route to meta‑substituted benzylamines via nitrile reduction, followed by acetal deprotection to unveil an aldehyde/primary alcohol handle for further functionalization.
  • Use as a masked aldehyde electrophile for late‑stage diversification on an aryl nitrile scaffold.

• Practical tips

  • Sequence planning is key: conduct base‑mediated or neutral steps first, reserve acidic manipulations for the final acetal deprotection.
  • Monitor by 1H NMR: characteristic acetal methine (~4.5–5.5 ppm region, literature) and ethoxy CH3 triplets (~1.1–1.3 ppm) aid in tracking integrity.

Reaction Conditions

The following are general literature-guided conditions pertinent to substrates bearing aryl nitriles and diethoxyacetals. They are not product specifications and should be optimized.

• Nitrile to amine (reduction)

  • H2 (3–10 bar) with Raney Ni or Pd/C in ethanol or 2‑propanol at 25–60 °C; monitor for acetal stability. Alternatively, BH3·THF (1.5–3.0 equiv) in THF at 0–25 °C, quench carefully.

• Nitrile to aldehyde (partial reduction)

  • DIBAL‑H (1.1–1.5 equiv) in toluene or DCM at −78 to −40 °C, fast quench to avoid over‑reduction. Acetal typically survives if strictly anhydrous and non‑acidic.

• Nitrile hydrolysis

  • Basic: NaOH or KOH (2–5 M) in EtOH/H2O, reflux; note that acetal will likely hydrolyze under these mixed aqueous/heat conditions.
  • Acidic: H2SO4 or HCl aqueous, 60–100 °C; expect rapid acetal cleavage—sequence steps accordingly.

• Acetal deprotection

  • p‑TsOH (5–10 mol%) in acetone/H2O or MeOH/H2O at 0–25 °C; or aqueous mineral acid (0.5–1 M) at ambient temperature. Work rapidly to avoid side reactions on the aryl ether.

• Transacetalization

  • Catalytic TsOH or HCl(g) in dry alcohol (ROH) at 0–25 °C under Dean–Stark or reduced pressure to remove exchanged alcohol byproduct.

• Purification/handling

  • Use neutralized silica or add 0.1–1% Et3N to eluents to minimize acetal cleavage. Keep strictly anhydrous for steps sensitive to hydrolysis.

Yields and times vary widely by substrate; begin with small‑scale trials and rigorous anhydrous technique to protect the acetal.

Safety and Handling

Safety details specific to this catalog item are not provided; consult the SDS for authoritative information.

• GHS/CLP classification (item-specific)

  • 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 hazards based on functional groups (literature/general guidance)

  • Aromatic nitriles and acetals are typically combustible organic liquids/solids; avoid heat, sparks, and open flame.
  • Acetals are generally of low acute toxicity but can hydrolyze to alcohols/aldehydes under acid and moisture; avoid strong acids to prevent decomposition and potential aldehyde release.

• Incompatibilities (general)

  • Strong acids (acetal hydrolysis), strong oxidizers, and strong electrophiles.
  • Prolonged exposure to acidic silica or acidified aqueous media.

• PPE and hygiene

  • Use lab coat, safety glasses, and appropriate chemical‑resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of vapors/aerosols. Wash thoroughly after handling.

• First aid (general overview; defer to SDS)

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Spill/fire response (general)

  • Absorb small spills with inert material; ventilate area. Use CO2, dry chemical, or foam for fire. Prevent entry into drains.

Always follow institutional EHS procedures and refer to the SDS for this SKU.

Solvent Selection

This molecule is an apolar-to-mid‑polarity aryl ether containing a nitrile and an acetal, favoring organic media.

• Polarity/miscibility (general behavior)

  • Expected to be insoluble or only sparingly soluble in water; readily soluble in ethers (THF, MTBE), chlorinated solvents (DCM, chloroform), esters (EtOAc), aromatics (toluene), and polar aprotics (acetonitrile, DMF, DMSO).
  • Dielectric environment: reactions involving the nitrile (e.g., reductions) often benefit from polar aprotics; transformations at the acetal are frequently run in nonprotic solvents to avoid hydrolysis.

• When to choose specific solvents (practical guidance)

  • Purification: hexanes/EtOAc or toluene/EtOAc gradients typically give good separation on silica; neutralized silica (with 1–2% triethylamine) can protect acetal functionality.
  • Nucleophilic substitutions or metalations on the aryl ring are uncommon; for benzylic/side‑chain chemistry, use THF or toluene depending on base.
  • Reductions of the nitrile to amine or aldehyde equivalents: THF, MeOH (if acetal is protected/compatible), or ethanol with carefully chosen catalysts; avoid protic acids.

• Comparison notes (general)

  • DCM vs toluene: DCM offers faster chromatography and good solubility; toluene is higher‑boiling and more benign from a green perspective.
  • THF vs 2‑MeTHF: 2‑MeTHF offers similar solubilization with improved sustainability and phase‑split workups.

Always confirm actual solubility with a small‑scale trial; defer to the CoA for any item-specific solvent restrictions.

Storage and Reconstitution

• Storage conditions (item-specific)

  • Storage: Room temperature (Product Data).
  • Shipped in: Normal (ambient) conditions (Product Data).

• General handling

  • Keep container tightly closed and stored in a dry, well‑ventilated area away from strong acids and oxidizers. Protect from prolonged exposure to moisture and acidic vapors to preserve the acetal functionality.
  • If transferred to working vials, use dry, clean glassware. For long‑term storage, consider adding a desiccant in the outer container and minimizing headspace.

• Stability notes (general)

  • Acetals are stable under neutral and basic conditions but can hydrolyze in the presence of acids and water. Avoid acidic silica during storage and purification.

• Reconstitution/solubilization

  • This compound is expected to dissolve readily in common organic solvents (e.g., DCM, THF, EtOAc, toluene, MeCN, DMSO). Select anhydrous grades to maintain acetal integrity. No aqueous reconstitution is recommended.

• Freeze–thaw guidance

  • Not typically required. If a lower storage temperature is chosen for formulation reasons, allow to warm to ambient in a sealed vial before opening to prevent moisture condensation.

Always refer to the product’s CoA and SDS for lot‑specific guidance and confirm compatibility with your application.

Structure and Identity

3-(3,3-Diethoxypropoxy)benzonitrile is an aromatic nitrile bearing a meta-alkoxy substituent that extends to a diethoxyacetal terminus.

• Item-specific identifiers

  • CAS: 1394041-76-9 (Product Data)
  • CID: 63629980 (Product Data)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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.

• Structural features (general description from name)

  • Core ring: substituted benzonitrile (benzene bearing a cyano group, –C≡N), providing a strongly electron‑withdrawing function and a handle for further transformation (e.g., to amide, amine, aldehyde).
  • Substitution pattern: the alkoxy substituent is in the 3‑position (meta) relative to the nitrile (i.e., 3‑alkoxybenzonitrile motif).
  • Side chain: “3,3‑diethoxypropoxy” denotes an –O–CH2–CH2–CH(R)(OEt) where R = OEt, i.e., a propoxy chain whose terminal carbon (C3) is an acetal carbon substituted with two ethoxy groups. This constitutes a mixed acetal (diethemiacetal) functionality.
  • Functional groups present: aryl ether (Ar–O–), nitrile (–C≡N), and acetal carbon bearing two –OEt substituents (acetal protecting group for an aldehyde equivalent).
  • Stereochemistry: none expected at the acetal center if it bears one hydrogen; no defined stereocenters are designated by the name.

• 2D structural description in words

  • A benzene ring with a cyano substituent; at the meta position, an oxygen linker connects to a three‑carbon chain ending in a tertiary acetal center substituted by two ethoxy groups.

Synthetic Utility

The combination of an aryl nitrile and a terminal diethoxyacetal confers complementary reactivity that is useful in route design.

• Nitrile reactivity (literature)

  • Reduction to primary amine (H2/Pd, Ni; BH3; catalytic transfer hydrogenation) enables subsequent acylation, urea/thiourea formation, or intramolecular cyclizations.
  • Partial reduction to aldehyde (DIBAL‑H, Schwartz reagent) provides access to benzaldehyde derivatives while retaining meta‑substitution topology.
  • Hydrolysis to amide/acid permits coupling strategies when amide bond formation is desired.

• Acetal as masked carbonyl

  • Acidic deprotection yields an aldehyde at the chain terminus, enabling aldol, Wittig, reductive amination, or cyclization chemistry.
  • Transacetalization can modulate stability/solubility without altering the aryl core.

• Aryl ether stability

  • Generally robust to bases and many reductants; choose Lewis/Brønsted acids judiciously.

• Retrosynthetic value

  • Disconnection through the acetal suggests late‑stage installation of the aldehyde to avoid over‑reduction or polymerization.
  • The nitrile can serve as a traceless directing group or as a synthetic linchpin convertible to multiple functionalities, aiding in scaffold hopping and parallel synthesis.

• Practical analytics

  • Monitor acetal integrity by 1H/13C NMR (acetal methine ~100–105 ppm in 13C, ethoxy CH3 ~15 ppm; literature, general) and LC/MS (M+H consistent with diethoxyacetal mass).

Target Specificity

Not applicable. This product is a small‑molecule chemical intermediate and is not an antibody, enzyme, or biological probe with defined target specificity. No antigen/epitope, clone, or isotype information applies.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1394041-76-9, the molecular formula is C14H19NO3, and the molecular weight is 249.3 g/mol. InChIKey LTHHZLOHKGENKX-UHFFFAOYSA-N.

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.