3-(Dimethoxymethyl)benzonitrile - ≥96% , CAS No.124283-45-0

CAS: 124283-45-0 Cat. No.: D964356 Formula: C₁₀H₁₁NO₂ Peso molecolare: 177.200

GRADE & PURITY ≥96%

Storage

Room temperature

Specifications

Specifiche e purezza

≥96%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥96%

Nomi e identificatori

• Sorrisi canonici: COC(C1=CC=CC(=C1)C#N)OC
• IUPAC Name: 3-(dimethoxymethyl)benzonitrile
• InChIKey: BTCNYDXETCMMLH-UHFFFAOYSA-N
• INCHI: 1S/C10H11NO2/c1-12-10(13-2)9-5-3-4-8(6-9)7-11/h3-6,10H,1-2H3
• Peso molecolare: 177.200

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzylethers
• Alternative Parents: Benzonitriles Nitriles Acetals Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzylether - Benzonitrile - Nitrile - Carbonitrile - Acetal - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
• 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: 177.200 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 177.079 Da
• Monoisotopic Mass: 177.079 Da
• Topological Polar Surface Area: 42.300 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 192.000
• 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 applications (WB, IHC, IF, FC, etc.) are provided for this small-molecule reagent. Usage is context-specific to synthetic organic chemistry workflows. For reaction protocols, see the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections.

Biological Roles

This is a small-molecule synthetic building block intended for chemical research. It is not a biomolecule, enzyme, or metabolite.

• Biological function: Not applicable; no known endogenous role. Any bioactivity would be incidental and context-dependent; no claims are made.
• Use context: Employed in organic synthesis to access meta-formylated benzonitriles and derivatives that may enter SAR studies or materials research.
• Note: Handle strictly as a laboratory reagent. For research use only (product data).

Buffer Applications

Not typically used as a buffering agent. As a neutral organic building block, it does not provide acid/base conjugate pairs for buffering.

• Recommendation: Select this reagent for synthetic transformations; for pH control in aqueous media use established buffer systems (e.g., phosphate, acetate, Tris) appropriate to your biological/analytical application.

Green Alternatives

Consider greener choices in solvents and protecting strategies while maintaining chemoselectivity for the nitrile and acetal.

• Greener solvent swaps (literature guidance): • Replace DCM with EtOAc, MeTHF/2-MeTHF, CPME, or toluene when feasible.
  • Substitute THF with 2-MeTHF for organometallic chemistry; 2-MeTHF is bio-based, has a higher boiling point (facilitating reactions) and easier phase splits, but can retain peroxides and water—validate drying/peroxide controls.

Comparison (general/literature):

• DCM vs EtOAc/2-MeTHF: • Environmental: DCM is halogenated with higher environmental and health burden; EtOAc and 2-MeTHF are preferable.
  • Performance: DCM offers strong elution/low bp; EtOAc/2-MeTHF may require temperature or time adjustments.
• Protecting-group strategy: • Dimethyl acetal is effective but methanol-intensive to form and acid-labile. Alternatives include ethylene glycol acetals (dioxolanes) that can be more robust under some conditions and may allow solvent recycling when formed in green media (e.g., 2-MeTHF, toluene with azeotropic water removal).
  • Direct use of the free aldehyde with in situ masking (e.g., imine or bisulfite adducts) can reduce protection/deprotection steps in specific sequences, but assess compatibility with the nitrile.

Trade-offs:

• Greener solvents may change rates/solubility; pilot trials are advised.
• Neutral/weakly basic workups help avoid acetal cleavage; strong aqueous acid workups, though efficient, can generate methanol and additional waste.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item. It is supplied for research and laboratory synthesis only.

• Potential roles (general R&D context, not clinical): • Intermediate in the preparation of more complex aromatic nitriles, amides, acids, aldehydes, and ketones that may be screened during discovery.
  • The dimethoxymethyl group serves as an aldehyde protecting group during route scouting.

No therapeutic or clinical claims are made. For formulation or GMP-related applications, refer to pharmacopeial standards and quality documentation specific to the intended substance.

Physical Properties

Item-specific specifications are not provided in the product data. The following are general/literature expectations for the chemical class and structure; verify against the CoA/SDS and primary literature for exact values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Compounds of this class are typically colorless to pale liquids or low-melting solids (literature, varies with purity and storage).
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature/computed estimate for C10H11NO2: ~177.20 g/mol.
• Boiling point / melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Aromatic acetal–nitriles of similar size often boil in the 250–300 °C range at ambient pressure or distill under vacuum (literature, broad guidance only). Solidification near/below room temperature is possible for some isomers.
• Density (20–25 °C): Not specified for this item; refer to CoA/Spec Sheet.
  • Aromatic nitriles typically 1.05–1.15 g/mL (literature trend, not item-specific).
• Solubility (literature expectations): • Low in water; miscible with common organic solvents (CH2Cl2, THF, EtOAc, toluene, MeCN, MeOH; acetal stability in protic/acidic media should be considered).
• Refractive index, UV cutoff, peroxide content, water content, trace metals: Not specified for this item; refer to CoA/Spec Sheet.
• LogP/pKa (literature expectations): • Aromatic nitriles with one acetal substituent typically show moderate hydrophobicity (cLogP likely ~1.5–2.5; literature/computed trend). No ionizable groups in neutral water; acetal is acid-labile but not acidic/basic per se.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Impurity profile controls often relevant for this class: • Hydrolysis products: 3-formylbenzonitrile (aldehyde) and methanol from acetal cleavage.
  • Over-alkoxylated or partially deprotected species.
  • Residual solvents from synthesis/purification.
  • Trace inorganic salts or acids from acetalization catalysts.
• What grade means (general guidance): • “Reagent” or “synthetic” grade: Suitable for most organic syntheses; impurities not specifically optimized for trace analytics.
  • “High-purity”/“HPLC” grades (when offered): Tighter control of non-volatile residue and UV background; useful when doing photochemical steps or trace analytics.
  • “Anhydrous” variants (when offered): Water specification controlled; beneficial for moisture-sensitive steps (e.g., organometallic additions to nitriles).
  • Stabilizers: Not typically required for acetals, but some lots may be prepared/handled under mildly basic conditions to suppress acid-catalyzed hydrolysis (if present, will be declared on CoA).
• Verification: For process-critical applications, confirm identity by 1H/13C NMR (diagnostic acetal CH ~5–6 ppm, OMe ~3.2–3.5 ppm; literature), IR (C≡N stretch ~2225 cm−1; acetal C–O), and GC/LC purity. Water and residual acid can be checked by Karl Fischer and acid number/titration respectively (if applicable).

Reaction and Applications

The molecule integrates two versatile synthetic handles: an aryl nitrile and a masked aryl aldehyde (dimethyl acetal). This enables orthogonal and sequential functionalizations under chemoselective conditions.

• As a masked aldehyde (literature): • Acidic deprotection (aqueous mineral acids, TFA, or Lewis acids) unveils 3-formylbenzonitrile. The acetal survives many basic and some neutral conditions, enabling aldehyde-intolerant steps to proceed first.
  • Useful in multistep sequences where direct exposure of the aldehyde would cause side reactions (e.g., with nucleophiles or bases).
• Nitrile transformations (literature): • Hydrolysis to amide/acid (acidic or basic conditions; base typically requires elevated temperature and water co-solvent).
  • Reduction: DIBAL-H to the imidate/aldehyde stage; LiAlH4 or BH3 to the benzylamine; catalytic hydrogenation under appropriate conditions.
  • Nucleophilic addition of organolithiums/Grignards to form imines that hydrolyze to ketones.
  • Metalation ortho to the nitrile (directing effects) enabling subsequent electrophile trapping.
• Cross-coupling (literature): • While the substrate lacks a halide, nitrile-directed C–H activation on arenes is documented with Pd/Rh catalysts; the acetal’s acid lability must be considered.
  • The nitrile can serve as a traceless directing group in some metalations followed by quench/elimination.
• Practical tips: • Keep acids out unless deprotection is intended; even mildly acidic silica can induce partial acetal cleavage—use neutralized silica or add 0.1–1% Et3N to eluents as needed.
  • For organometallic additions to the nitrile, ensure rigorously dry conditions; quench at low temperature to control exotherm and byproducts.
• Applications context: Building block for meta-formylated benzonitrile derivatives, heteroaryl–aryl linkages after aldehyde-based condensations (e.g., Knoevenagel with active methylenes), and for preparing amides/acids/ketones adjacent to a meta CN.

Reaction Conditions

The following conditions are general literature guidance for functional groups present in this molecule. They are not item-specific specifications.

• Acetal deprotection to 3-formylbenzonitrile (literature): • Reagents: Aqueous HCl (1–3 M), p-TsOH (5–10 mol%), or TFA in MeOH/THF/H2O.
  • Conditions: 0–25 °C to control side reactions; typical times 0.5–4 h depending on acid strength and solvent.
  • Workup: Neutralize, extract into nonpolar solvent; monitor by TLC/LC–MS (loss of acetal CH ~5–6 ppm in 1H NMR).
• Nitrile hydrolysis (literature): • Acidic: H2SO4/H2O, reflux (6–24 h) → amide/acid (longer/stronger for acid).
  • Basic: NaOH/KOH in EtOH/H2O or dioxane/H2O, reflux (8–24 h) → amide then acid after extended times; acidify to isolate acid.
• Nitrile reduction (literature): • To aldehyde: DIBAL-H (1.1–1.5 eq) in toluene/CH2Cl2/THF, −78 to −20 °C, then careful quench.
  • To amine: LiAlH4 (2–4 eq) in THF/Et2O, 0– reflux; or catalytic hydrogenation (Raney Ni/Pd/C) under H2 (1–10 bar, 20–60 °C). Evaluate acetal compatibility; stronger reductants/bases can risk cleavage.
• Organometallic addition to nitrile (literature): • RMgX/RLi (1.2–2.0 eq) in dry THF/Et2O/2-MeTHF at −78 to 0 °C; aqueous workup to afford ketone. Protect the acetal from acid during quench (buffered NH4Cl vs strong mineral acid).
• Purification considerations: • Neutralize silica with 0.1–1% Et3N to minimize acetal loss.
  • Avoid protic acids in eluents; use hexanes/EtOAc or toluene gradients.

Safety and Handling

Item-specific GHS classification and statements are not provided; consult the SDS for authoritative guidance.

• GHS signal word / pictograms / H-statements: Not specified for this item; refer to SDS.
• General hazards (class-based, literature): • Aromatic nitriles may cause irritation to skin, eyes, and respiratory tract.
  • Acetals are typically combustible organic liquids/solids. Avoid ignition sources.
  • Acid-labile acetal: contact with strong acids can generate the corresponding aldehyde (3-formylbenzonitrile) and methanol; manage vapors accordingly.
• PPE (standard lab practice): Lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and accidental byproducts (e.g., methanol upon acid hydrolysis).
• Handling notes: • Avoid strong acids and acid catalysts unless intentional deprotection is desired.
  • Keep containers tightly closed; minimize exposure to moisture and heat.
  • Ground/bond when transferring flammable liquids.
  • Prevent contact with oxidizers and strong electrophiles.
• First aid (overview; defer to SDS): • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice for persistent irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire response: Use CO2, dry chemical, or foam. Cool containers with water spray from a safe distance.
• Spill response: Absorb with inert material; collect in suitable container for disposal. Prevent entry to drains.

Solvent Selection

This product is an aromatic nitrile bearing an acid-labile dimethyl acetal. Solvent choice is driven by solubility and acetal stability.

• Polarity/miscibility (literature expectations): • Sparingly soluble in water; readily soluble in common organics (DCM, EtOAc, THF, MeCN, toluene, MTBE).
  • Protic solvents (MeOH, EtOH) are generally fine under neutral/basic conditions but, in the presence of acid, can promote acetal exchange or cleavage.
• Selecting solvents by task: • Routine handling, chromatography: DCM/EtOAc/hexanes systems perform well; toluene or EtOAc for crystallization where applicable.
  • Acid-sensitive operations: Prefer neutral, aprotic media (toluene, DCM, THF, 2-MeTHF). Avoid trace mineral acids; pre-neutralize silica for column work if aldehyde formation is problematic.
  • Organometallic additions to the nitrile: Use rigorously dry ethereal/THF/2-MeTHF solvents under inert atmosphere.
• Comparisons (general): • THF vs 2-MeTHF: Similar solvation for organometallics; 2-MeTHF is often greener and more hydrophobic, aiding phase separations.
  • DCM vs EtOAc: DCM offers strong elution and low bp; EtOAc is greener and less dense but may participate in transacetalization under strong acid.
• Additives: Use of bases (e.g., Et3N, Na2CO3) can suppress unintended acid-catalyzed acetal cleavage during workup; remove bases thoroughly after processing.

Storage and Reconstitution

• Storage conditions: Room temperature (product data). Store tightly closed in a dry, well-ventilated area away from acids and moisture to preserve the acetal functionality.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Stability considerations (general): • Acetal functionality is acid-labile; avoid acidic environments, acidic desiccants, or prolonged contact with acidic silica.
  • Protect from excessive heat and light to minimize decomposition.
• Reconstitution/Preparation: • The material is typically used neat or dissolved in anhydrous organic solvents (e.g., DCM, THF, toluene, MeCN).
  • If solidified, warm gently to room temperature and homogenize before use.
  • For moisture-sensitive operations (e.g., organometallic chemistry), pre-dry solvents and glassware; consider brief vacuum/nitrogen cycles of the container headspace prior to dispensing.
• Freeze–thaw: Not generally applicable; avoid unnecessary temperature cycling to prevent condensation in the container.
• For long-term quality: Periodically check by 1H NMR/IR for signs of acetal cleavage (emergence of aldehyde CH ~10 ppm; IR C=O ~1690–1720 cm−1). Refer to the SDS and CoA for definitive handling guidance.

Research Use Only (product data).

Structure and Identity

Research-use reagent: meta-substituted aromatic nitrile bearing a masked aldehyde as a dimethyl acetal.

• Product name: 3-(Dimethoxymethyl)benzonitrile (meta-(dimethoxymethyl)benzonitrile)
• CAS: 124283-45-0 (product data)
• CID: 85604658 (product data)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: A representative (literature) SMILES for this structure is often written in the form N#Cc1cccc(c1)C(OC)OC, reflecting a benzonitrile ring with a –CH(OMe)2 substituent at the meta position.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature/computed expectation for 3-(dimethoxymethyl)benzonitrile: C10H11NO2 (see rationale below).
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature/computed estimate for C10H11NO2: ~177.20 g/mol.

Structural description (general/literature):

• Core: A benzene ring bearing a nitrile (–C≡N) and a dimethoxymethyl group (–CH(–OCH3)2) in a meta (3-) relationship.
• Functional groups: Aromatic ring, aryl nitrile (strongly electron-withdrawing), and an acetal (dimethyl acetal) that serves as a protected aldehyde equivalent.
• 2D arrangement in words: Starting from the nitrile carbon on the ring as position 1, the dimethoxymethyl substituent is located at the 3-position (meta). The –CH(OMe)2 carbon is sp3 and attached directly to the aromatic carbon; each methoxy is bound via an oxygen to this same carbon.
• Stereochemistry: None (achiral as drawn).

Synthetic Utility

Dual-handle platform for divergent synthesis:

• Dimethoxymethyl as a protected aldehyde (literature): • Deprotect to 3-formylbenzonitrile under acidic conditions; then engage in condensations (Knoevenagel, aldol variants, Wittig/Still–Gennari/HWE on the aldehyde).
  • Tolerates many bases/nucleophiles that would otherwise attack a free aldehyde.
• Nitrile reactivity (literature): • Hydrolysis to amide/acid (H+/H2O or OH−/H2O, heat).
  • Reduction: DIBAL-H to aldehyde (via imidate), LiAlH4/BH3 to benzylamine; catalytic hydrogenation to primary amine under suitable catalysts.
  • Organometallic addition (RLi/RMgX) → imine/imine–Mg/Li intermediate → hydrolysis to ketone (useful for aryl–alkyl or diaryl ketone synthesis meta to CN).
  • Directed metalation ortho to the nitrile enabling electrophile installation; acetal stability under strong bases should be evaluated case-by-case.
• Orthogonality: • Many transformations can be performed at the nitrile without unmasking the aldehyde; final acidolysis then reveals the aldehyde for downstream coupling.
• Retrosynthetic value: • Serves as a masked 3-formylbenzonitrile synthon where acid-sensitive steps precede unveiling of the aldehyde.
• Practical guidance: • Control moisture and avoid acids to preserve the acetal.
  • For metalations/additions, use dry ethereal solvents, low temperature, and cautious quench to minimize acetal cleavage.

Target Specificity

Not applicable. This product is a small-molecule organic reagent and is not an antibody, probe, or biological targeting agent. No target specificity data are provided in the product data.