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
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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.
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Application Protocols
Not applicable. No validated bioassay or immunoassay protocols (WB, IHC, IF, FC) apply to this small-molecule building block. For synthetic use, refer to Reaction Conditions and Synthetic Utility sections for general procedures.
Biological Roles
Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet. For research use only.
General context (literature):
Aromatic nitriles are common motifs in agrochemicals and pharmaceuticals as metabolically robust, polarity-tuning groups; however, the presence of a nitrile in a small molecule does not imply any particular biological activity by itself.
The 2-methoxyethoxy substituent is a solubilizing moiety frequently used to adjust lipophilicity and permeability in medicinal chemistry scaffolds.
No endogenous biological role is expected for this synthetic aromatic nitrile; any biological testing should be conducted under appropriate research approvals.
No medical or clinical claims are made; this product is supplied strictly for research and laboratory use.
Buffer Applications
This compound is a non-ionic organic building block and is not used to formulate laboratory buffers. It lacks acid/base functionality in the physiological pH range (the nitrile is not protonated/deprotonated under typical buffer conditions).
Guidance: If aqueous work is required (e.g., hydrolysis), select a compatible buffer or aqueous medium based on the transformation (mineral acids/bases for hydrolysis), and use a co-solvent (MeCN, EtOH, dioxane) to enhance solubility.
Green Alternatives
For this compound as a building block, “green alternatives” relate mainly to solvent and reagent choices during its transformations.
Greener solvent choices (literature/general):
Replace chlorinated solvents (DCM) with ethyl acetate, 2-MeTHF, or CPME when compatible.
For reductions/hydrogenations, ethanol or 2-propanol can be used as greener media with supported catalysts, avoiding pressurized toxic solvents.
For hydrolyses, aqueous ethanol or water-rich mixtures reduce solvent burden.
Reagent alternatives and trade-offs:
Demethylation: BBr3 is effective but hazardous; consider catalytic oxidative demethylations (e.g., DDQ under controlled conditions) or aluminum chloride-free methods where feasible. Trade-off is lowered functional group tolerance/efficiency.
Nitrile to amide/acid: Enzymatic nitrilases/amidases in aqueous media offer greener routes but may have limited substrate scope and require optimization.
Nitrile reductions: Transfer hydrogenation (formic acid/triethylamine, ammonium formate) or catalytic hydrogenation in alcohols can replace LiAlH4; trade-offs include selectivity and longer reaction times.
Mini comparison (general):
DCM/BBr3 demethylation: rapid, low temperature; high hazard/halogenated waste.
2-MeTHF/TMSI or iodide-promoted systems: reduced chlorinated waste; may require higher equivalents and careful quench.
Aqueous base hydrolysis vs. neat acid chloride formation routes: fewer steps and less phosgene-equivalents, but may need longer heating.
Pharmaceutical Uses
Item-specific pharmacopeial status/excipient role: Not specified for this item; refer to CoA/Spec Sheet.
General information (non-clinical):
3-(2-Methoxyethoxy)benzonitrile may serve as a research intermediate in the synthesis of meta-substituted benzamides, benzoic acids, benzylamines, and derived heterocycles after functional group interconversion.
Potential roles in pharmaceutical R&D are limited to process/intermediate usage, impurity standards, or structure–activity relationship exploration.
No therapeutic or clinical claims are made; for research and manufacturing development use only.
Physical Properties
Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed properties (reference only; not item-specific):
Physical state at ambient: typically a low-melting solid or high-boiling liquid for similar aryl nitriles with short ether chains.
Approximate formula weight: ~177.20 g/mol (from C10H11NO2 calculation).
Polarity: moderately polar (aryl nitrile and ether functions), substantially less polar than DMSO/DMF but more polar than toluene/ethyl acetate.
Solubility (qualitative):
Good solubility in common organic solvents (EtOAc, DCM, THF, MeCN, acetone, toluene).
Low solubility in water expected for aryl nitriles with short ether chains.
Partitioning: cLogP is expected in the ca. 1.5–2.5 range (software-dependent, estimated for related structures).
UV: aromatic chromophore and nitrile typically show strong absorption in the 200–230 nm range and a weaker band 250–280 nm (literature, general for benzonitriles).
Practical notes (general):
The nitrile is hydrolytically robust under neutral conditions; prolonged strong acid/base and high temperature can lead to hydrolysis to amide/acid (see Reaction & Applications).
The aryl–O–(CH2)2–OCH3 chain increases organic solvent solubility and may depress crystallinity relative to unsubstituted benzonitrile.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret common grades for this type of building block (general guidance):
Research grade: Suitable for most synthetic applications; impurity profile may include trace starting materials and isomers.
≥98% (typical high-purity for fine chemicals): Preferred for SAR/medchem work to minimize background in analytical assays and downstream steps.
HPLC or GC assay basis: Confirms purity by chromatographic method; UV cutoffs are more relevant to solvents than to small-molecule building blocks.
Stabilizers/inhibitors: None are typically required for aryl nitriles/ethers. If a stabilizer were present, it would be declared on the CoA/SDS; absence here means Not specified for this item; refer to CoA/Spec Sheet.
What to check on receipt:
Identity confirmation by 1H/13C NMR and HRMS.
Purity by HPLC/GC; check for regioisomeric impurities.
Water content (if relevant to your application): Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
As an aryl nitrile bearing an aryl–O–(CH2)2–OCH3 chain, this molecule is a versatile intermediate in organic synthesis.
Transformations of the nitrile (literature/general):
Hydrolysis: to amide (–CONH2) under milder acidic/basic conditions, and further to carboxylic acid under more forcing conditions (H2O/acid or base, heat). Pinner reaction to imidates possible under alcoholic HCl.
Reductions:
To the corresponding benzylamine (aryl–CH2–NH2) via catalytic hydrogenation (Pd/C, Raney Ni) or LiAlH4 in etheral solvents.
To the aldehyde using DIBAL-H at low temperature (≤ −78 °C), with careful quench.
Nucleophilic addition: Grignard/organolithium reagents add to nitriles to afford ketones after acidic hydrolysis of the intermediate imine/imidate.
Transformations of the aryl ether (literature/general):
O-Dealkylation/demethylation: BBr3, BCl3, or TMSI to access the corresponding meta-(2-hydroxyethoxy)benzonitrile or resorcinol derivatives after further cleavage.
Oxidation of side chain: Generally resistant; ether cleavage preferred over oxidation under many conditions.
Strategic applications:
Scaffold for meta-substituted benzoic acid or benzylamine derivatives following nitrile conversion; the 2-methoxyethoxy group serves as a lipophilicity and solubility modulator.
Handle for late-stage diversification: nitrile can be a masked carbonyl (acid/amide/aldehyde/ketone), enabling rapid library expansion in medchem.
Practical tips:
Electron-withdrawing nitrile deactivates the ring toward electrophilic substitution; cross-coupling typically requires a halide handle (not present here). Plan functional group interconversions first.
Protect against strong Lewis acids if the ether moiety must be retained.
Reaction Conditions
General literature guidance for transformations of aryl nitriles/ethers (adjust to your scale and safety protocols):
Nitrile hydrolysis to amide/acid:
Acidic: conc. H2SO4 or HCl, H2O, 80–120 °C; amide at shorter times, acid on prolonged heating. Mixed solvent (dioxane/water) can improve solubility.
Basic: NaOH or KOH in EtOH/H2O or MeOH/H2O, reflux to 100–120 °C (sealed vessel) until completion; acidify to isolate the acid.
Reduction:
To benzylamine: LiAlH4 (2–4 equiv) in dry THF or Et2O, 0 °C to reflux; or H2 (3–10 bar) over Pd/C or Raney Ni in EtOH/MeOH at 25–60 °C until uptake ceases.
To aldehyde: DIBAL-H (1.3–2.0 equiv) in dry toluene or CH2Cl2, −78 to −40 °C; careful aqueous Rochelle’s salt quench.
Ketone formation via organometallic addition:
Add RMgX or RLi (1.2–2.0 equiv) in dry THF at −78 to 0 °C, then warm; hydrolyze the imine/imidate to the ketone with aqueous acid workup.
O-Dealkylation/demethylation:
BBr3 (1–3 equiv per methoxy) in dry DCM, −78 to 0 °C; quench with MeOH/H2O; monitor to avoid overcleavage of the –O–CH2–CH2–O– segment.
Alternative: TMSI generated in situ from NaI/Me3SiCl in acetonitrile, reflux.
Workup/analytics:
Monitor by HPLC/GC or TLC (UV 254 nm). Typical isolated yields for such conversions in literature range from 60–90%, depending on conditions and scale.
These are general conditions from literature precedent and should be optimized for your substrate and setup.
Safety and Handling
Item-specific hazard data (GHS, H/P statements, pictograms): Not specified for this item; refer to the SDS for authoritative information.
General safety guidance for aromatic nitriles and aryl ethers (literature/general):
Hazards: May cause skin/eye irritation and respiratory tract irritation. Aromatic nitriles are not equivalent to inorganic cyanides but should be handled to avoid ingestion and inhalation.
PPE: Use lab coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid vapor/aerosol exposure.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Incompatibilities (general): Strong oxidizing agents; strong acids or bases at elevated temperature can promote nitrile hydrolysis or ether cleavage. Avoid prolonged exposure to moisture during strong basic/acidic handling steps.
Thermal stability: Aryl nitriles are typically thermally stable; avoid overheating and open flames.
Waste: Collect organic waste and dispose in accordance with institutional and local regulations.
Always consult the product-specific SDS before use.
Solvent Selection
This product is a synthetic building block, not a solvent. Solvent choice pertains to its use in reactions or analytical work.
Polarity/miscibility considerations (general for aryl nitriles with ether chains):
Expected to dissolve well in mid-polar aprotic solvents (EtOAc, THF, MeCN, acetone, DCM) and in aromatic hydrocarbons (toluene).
Limited aqueous solubility; aqueous-organic biphasic systems may require phase-transfer catalysts or co-solvents.
Typical use scenarios and solvent picks:
Hydrolysis of nitrile to amide/acid: mixed aqueous mineral acid or base in MeOH/EtOH, dioxane, or acetonitrile; elevated temperature.
Reduction of nitrile: anhydrous ethereal solvents (THF, Et2O) for metal hydrides; alcohols or acetic acid for catalytic hydrogenation.
Demethylation/ether cleavage: halogenated solvents (DCM) for BBr3/BCl3 or TMSI at low temperature.
Grignard/organolithium addition to nitrile: dry THF or Et2O under inert atmosphere.
Analytical:
HPLC sample prep: acetonitrile or methanol, possibly with 0.1% acid for improved peak shape; detection by UV at ~220–254 nm (literature, general).
Comparison note:
Relative to unsubstituted benzonitrile, the 2-methoxyethoxy substituent enhances solubility in polar aprotic media, facilitating higher-concentration reactions.
Storage and Reconstitution
Item-specific storage: Room temperature (from Product Data). Shipped under normal conditions.
General handling advice (literature/general):
Store in a tightly closed container, protected from moisture and strong light; an amber vial is recommended for extended storage.
If low-temperature storage is desired for long-term stability studies, ensure the material is dry to prevent condensation on warming.
Avoid prolonged exposure to strong acids/bases in storage; the nitrile and ether are stable under neutral, dry conditions.
Reconstitution:
Solid or viscous material can be dissolved in common organic solvents (e.g., acetonitrile, THF, ethyl acetate, dichloromethane) to prepare stock solutions.
For moisture-sensitive reactions, pre-dry solvents and handle under inert atmosphere.
Shelf-life: Not specified for this item; refer to CoA/Spec Sheet.
Research use only.
Structure and Identity
A meta-substituted aromatic nitrile bearing a 2-methoxyethoxy solubilizing ether chain.
Item-specific (from Product Data):
SKU: M186699
Product name: 3-(2-Methoxyethoxy)benzonitrile
CAS: 80407-67-6
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (for reference; not item-specific):
One literature SMILES representation: COCCOc1cccc(C#N)c1 (meta-arrangement of nitrile and ether substituent)
Empirical formula (derived from structure): C10H11NO2 (literature)
Formula weight: ~177.20 g/mol (literature)
Structural features (general description):
Aromatic ring bearing a nitrile (–C≡N) at the 1-position and a 2-methoxyethoxy substituent (–O–CH2–CH2–O–CH3) at the 3-position (meta).
Functional groups: aryl nitrile (electron-withdrawing), aryl ether (weakly electron-donating via resonance but attenuated by –O–CH2– linkage), aliphatic ether.
2D topology (in words): a benzene ring with a linear C≡N group and a flexible ethoxy-ethoxy-methyl chain connected through an aryl–O bond; no stereocenters.
Polarity pattern: polar nitrile and ether oxygens on an otherwise hydrophobic aromatic core, yielding amphiphilic character suitable for organic media.
Key functional elements: an aryl nitrile (electrophilic carbon of C≡N) and an aryl ether (potentially cleavable/protecting group-like substituent), positioned meta to each other.
Retrosynthetic value (literature/general):
Nitrile as a convertible handle:
→ Amide/acid via hydrolysis (pH- and temperature-controlled).
→ Aldehyde via DIBAL-H; → Ketone via RMgX/RLi addition and hydrolysis; → Benzylamine via hydride or catalytic hydrogenation.
Ether as a modulator/protecting element:
O-Dealkylation to reveal phenolic OH enabling further diversification (sulfonates, halogenation via diazotization if converted to anilide after nitrile reduction, etc.).
Library synthesis ideas:
Parallel hydrolyses to benzamides with varied amine couplings (after acid formation), exploiting the meta relationship to explore SAR.
Reductive routes to m-(2-methoxyethoxy)benzylamines for subsequent urea/carbamate/sulfonamide formation.
Compatibility notes:
The nitrile tolerates many oxidants and bases; avoid strong Lewis acids if the ether must be retained.
Electrophilic aromatic substitution is deactivated; introduction of additional ring substituents is better achieved via metalation strategies (ortho to ether) or via prefunctionalized precursors.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope or species reactivity applies.
Frequently Asked Questions
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 80407-67-6, the molecular formula is C10H11NO2, and the molecular weight is 177.2 g/mol. InChIKey QBSDNRJPVUFLJW-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.
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