This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
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 biological assay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block in the Product Data. For chemical usage, see Reaction Conditions and Application notes in the relevant sections.
Biological Roles
This product is an aromatic dinitrile building block without known intrinsic biological function. No biological roles are specified in the Product Data. Not specified for this item; refer to primary literature if exploring bioactivity of derivatives.
General context (non-clinical, literature):
Aromatic nitriles can appear in medicinal chemistry as electrophile-tuned, metabolically stable motifs; however, 2,5-dimethylterephthalonitrile itself is primarily used as a synthetic intermediate rather than a probe or ligand.
The –C≡N group is metabolically robust and can modulate physicochemical properties (e.g., lipophilicity, polarity) in small molecules, but direct biological target engagement is uncommon without additional pharmacophores.
For laboratory R&D only: Any evaluation of biological activity must be performed under appropriate regulatory and safety frameworks. No medical or clinical claims are made for this material.
Buffer Applications
Not typically applicable. 2,5-Dimethylterephthalonitrile is a neutral, hydrophobic organic solid and does not serve as a buffering agent or pH stabilizer. For experimental planning, refer instead to the Solvent Selection, Reaction & Applications, and Synthetic Utility sections that address its use as a chemical building block.
Green Alternatives
While the substrate itself is a building block rather than a solvent, greener choices can be implemented in reactions that modify its nitrile groups.
Conventional: Conc. mineral acids or strong base in DMF/NMP at high temperature.
Greener: Aqueous base or acid in water/ethanol mixtures with phase-transfer catalysis or microwave assistance to reduce solvent/toxicity and energy demand.
Reduction to diamines:
Conventional: LiAlH4 in ether or BH3·THF (pyrophoric, hazardous quench).
Greener: Catalytic hydrogenation over Raney Ni or Pd/C in EtOH or iPrOH, sometimes with ammonia to suppress imine hydrogenation side products; avoids stoichiometric hazardous hydrides.
Tetrazole synthesis:
Conventional: DMF at 120 °C with ZnCl2.
Greener: Deep eutectic solvents or water/ethanol with benign Lewis acids (e.g., Zn(II) salts in H2O/EtOH) and mechanochemistry where feasible.
Comparison snapshot (general):
DMF/NMP vs bio-based ethers (2-MeTHF)/alcohols: 2-MeTHF or EtOH reduce toxicity/worker exposure but may limit solubility; consider temperature escalation or co-solvents.
Mineral acids vs solid acids: Sulfonated resins (Amberlyst), heteropolyacids, or supported catalysts can facilitate hydrolysis/esterification with simplified workup and lower corrosivity.
Use recyclable solvents (EtOAc, MeTHF) and implement solvent recovery; ensure robust aqueous workup to minimize amide/acid carryover.
Pharmaceutical Uses
No pharmacopeial grade or excipient status is provided. Not specified for this item; refer to CoA/Spec Sheet.
General formulation/manufacturing context (non-clinical, literature):
Role: Typically a synthetic intermediate in upstream medicinal chemistry or process development to access diacids, diamides, diamines, or heterocycles (e.g., tetrazoles). It is not used as a finished excipient.
Handling in discovery workflows: Stock solutions can be prepared in DMSO or DMF for parallel synthesis. For scale-up transformations (e.g., hydrogenation to diamines), selection of GMP-compliant solvents and catalysts would be required if intermediates are destined for cGMP routes.
Purification: Crystallization from aromatic or polar aprotic solvents is common; avoid high-boiling toxic solvents where possible to streamline residual solvent clearance.
No therapeutic claims are made; this material is for research use only.
Physical Properties
Item-specific physical specifications (bp, mp, density, refractive index, assay) are not provided in the Product Data for this SKU. Not specified for this item; refer to CoA/Spec Sheet.
General physicochemical profile (literature/expected for this structure; non-specification):
Aggregated polarity: Despite two polar nitriles, the compact aromatic core and two methyl groups confer overall moderate polarity and low hydrogen-bond basicity; solid at ambient conditions is typical for para-dicyanobenzenes.
Volatility: Aromatic dinitriles are generally low-volatility, thermally robust solids with negligible vapor pressure at room temperature (literature, general class behavior).
Solubility (qualitative, literature/general):
Poor in water due to lack of hydrogen-bond donors and hydrophobic ring.
Soluble to moderately soluble in high-boiling polar aprotic solvents (DMF, DMAc, NMP, DMSO).
Often soluble in chlorinated organics (e.g., dichlorobenzene, chlorobenzene) and hot aromatic hydrocarbons; limited in hexanes/heptane.
Partitioning: Expected high logP/logS relative to terephthalonitrile due to the two additional methyl groups (literature, qualitative comparison).
Thermal behavior: Nitrile functionalities are thermally stable; hydrolysis requires strong acid/base and elevated temperatures (general chemistry knowledge).
If precise mp, thermal transitions (DSC), or solubility limits are required for process design or crystallization, please consult the Certificate of Analysis or request a detailed Spec Sheet for this production lot.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and best practice (general guidance):
Research use only: This material is intended for laboratory R&D. It is not for human or animal use, drug, or diagnostic applications.
When grade is unspecified for building-block solids, users should verify:
Assay method and basis (e.g., GC, HPLC, qNMR) and impurity profile (e.g., residual solvents, isomeric/byproduct content).
Residual inorganic content (sulfated ash/metals) if using in catalysis or optoelectronic materials.
Particle size or crystal form where dissolution and crystallization kinetics matter.
Water content (Karl Fischer) if using in moisture-sensitive reactions. Not specified for this item; refer to CoA/Spec Sheet.
UV/fluorescence background: For photophysical studies, confirm baseline UV-vis features and absence of fluorescent impurities. Not specified for this item; refer to CoA/Spec Sheet.
What is item-specific here:
Defined storage: 2–8°C, protected from light, desiccated; shipped on wet ice to preserve dryness and limit photodegradation.
Recommendation: Request a recent CoA for the exact lot to confirm assay, water, and residual solvent data prior to scale-up or analytical qualification.
Reaction and Applications
As a bifunctional aromatic dinitrile, 2,5-dimethylterephthalonitrile serves as a versatile intermediate for constructing electron-deficient aromatic scaffolds and linkers.
Key application families (literature/general):
Hydrolysis to diacids/diamides: Under strong acid (H2SO4/HCl) or base (NaOH/KOH) at elevated temperature, nitriles undergo stepwise hydrolysis (nitrile → amide → acid), enabling access to 2,5-dimethylterephthalic acid or the corresponding diamides/esters (via Pinner route).
Pinner/Imidate chemistry: Alcoholic HCl converts nitriles to imidate salts, which furnish diamidines, diamides, or diesters after appropriate trapping.
Reduction to diamines: Catalytic hydrogenation (Pd/C, Raney Ni) or hydride reagents (LiAlH4, BH3) reduce nitriles to primary amines, affording 2,5-dimethyl-1,4-bis(aminomethyl)benzene — a useful monomer for polyamides, polyureas, or crosslinkers.
Tetrazole formation: [3+2] Cycloaddition of azide to nitriles (often Zn2+ or Al3+ catalyzed in DMF/DMSO) yields 1,4-bis(tetrazolylmethyl) analogs, valuable as high-nitrogen ligands or energetic-material motifs.
Crosslinkable cores in materials: The strong –CN withdrawers lower LUMO levels; derivatives serve in donor–acceptor conjugated systems, OLED/OPV acceptors, and as precursors to rigid diacids for polyesters/co-polyamides.
Practical notes:
Electron-poor ring resists electrophilic substitution but can facilitate benzylic functionalization/oxidation of the 2,5-methyl groups.
Maintain anhydrous conditions for reductions; for hydrolysis, ensure sufficient water activity and base/acid concentration to avoid incomplete conversion to amide half-products.
The symmetry (para-dinitrile) simplifies product distributions in bifunctional conversions.
Reaction Conditions
The following are general literature conditions for common nitrile transformations applied to para-dicyano aromatics. These are guidance only, not product specifications.
Acidic hydrolysis (to diacid):
Solvent: Aqueous mineral acid (6–12 M HCl or H2SO4) or water/EtOH.
Temp/time: 80–130 °C, 6–24 h; pressure vessel for >100 °C.
Notes: Stepwise via diamide; excess water and extended time push to diacid. Work up by neutralization and crystallization.
Basic hydrolysis (to diacid via amide):
Solvent: Aqueous NaOH/KOH (2–6 M), often with co-solvent (EtOH, DMSO) for solubility.
Temp/time: Reflux (80–120 °C), 8–24 h.
Notes: After hydrolysis to carboxylates, acidify to precipitate diacid.
Reagents: Anhydrous ROH, dry HCl (g) or acetyl chloride + ROH to generate HCl in situ.
Temp/time: 0–25 °C for imidate formation; subsequent warming (25–60 °C) for trapping.
Notes: Exclude water; use inert atmosphere.
Reduction to diamine:
Catalytic hydrogenation: Pd/C or Raney Ni; solvent EtOH/iPrOH/EtOAc; 3–10 bar H2; 25–80 °C; 4–16 h. Add NH3 to suppress secondary amine formation.
Hydride: LiAlH4 in THF/Et2O; 0 °C → reflux; 2–8 h; cautious quench.
Tetrazole formation:
Reagents: NaN3 with ZnCl2 or AlCl3; solvent DMF/DMSO; 80–120 °C; 8–24 h.
Notes: Water workup removes metal salts; safety review for azide handling is mandatory.
Typical isolated yields (literature, method-dependent): 60–90% for stepwise hydrolysis products; 70–95% for diamines by catalytic hydrogenation; 50–80% for tetrazoles depending on activation and solubility.
Safety and Handling
Hazard classification for this specific item is not provided in the Product Data. Not specified for this item; refer to SDS for authoritative GHS classification, pictograms, signal word, and H-statements.
General safety guidance for aromatic nitrile solids (informational):
Potential hazards: Dust may cause mechanical irritation to eyes and respiratory tract. Aromatic nitriles are not cyanide salts and do not liberate HCN under ambient, neutral conditions; however, thermal decomposition or strong acid/base hydrolysis at high temperature can generate irritant/toxic species (e.g., amides, acids, ammonia). Avoid inhalation of dust and decomposition fumes.
PPE: Use lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to minimize dust and solvent vapor exposure.
Incompatibilities: Strong oxidizers. Extended exposure to strong bases or strong acids at elevated temperature promotes nitrile hydrolysis. Avoid moisture ingress if long-term dryness is required for sensitive transformations.
Fire fighting: Combustible organic solid; use CO2, dry chemical, or foam. Combustion may produce NOx and CO/CO2.
First aid (overview): Move to fresh air if inhaled; rinse cautiously with water for eye/skin contact; seek medical attention if irritation persists. If swallowed, rinse mouth; do not induce vomiting unless directed by medical personnel.
Storage per Product Data: Store at 2–8°C, protected from light, desiccated. Shipments are on wet ice. Always consult the product SDS before use.
Solvent Selection
This compound is a neutral, hydrophobic aromatic dinitrile solid. Solvent choice is usually dictated by the planned transformation (hydrolysis, reduction, cycloaddition) and desired concentration.
Polarity class: Non-protic, moderately polarizable aromatic core with two strongly polar nitriles; overall solvation benefits from polar aprotic media.
Preferred solvents (general/literature):
Polar aprotic: DMF, DMAc, NMP, DMSO — good solvating power for nitriles; useful for cycloadditions and metal-catalyzed reductions.
Chlorinated aromatics: Chlorobenzene, o-dichlorobenzene — effective for high-temperature operations (reflux >130 °C) and poor solubility cases.
Aromatics: Toluene/xylene — may require heating; lower polarity can limit rates of ionic transformations.
Alcoholic media: EtOH/MeOH are suitable for Pinner conditions (alcoholic HCl) but otherwise show limited solubility at room temp.
Generally poor: Alkanes (hexanes/heptane) and water.
Small comparison (general guidance):
DMF vs DMSO: DMF often offers lower viscosity and easier workup; DMSO can increase rates for azide–nitrile cycloaddition but is harder to remove.
NMP/DMAc: Similar to DMF with higher boiling points; helpful for elevated-temperature hydrolysis.
Chlorobenzene vs toluene: Chlorobenzene provides higher reflux temperature to drive sluggish reactions while remaining less polar than DMF.
Practical tips:
For moisture-sensitive reductions (e.g., LiAlH4), use rigorously anhydrous ethers (THF/Et2O) with pre-dried substrate.
For heterogeneous hydrogenations, choose a solvent that wets the catalyst and dissolves substrate at operating temperature (e.g., EtOH, iPrOH, or AcOEt/EtOH mixtures).
Storage and Reconstitution
Storage (from Product Data): Store at 2–8 °C, protected from light, desiccated. Shipments are on wet ice. Keep container tightly closed under dry, inert atmosphere if long-term storage is anticipated.
Stability considerations (general): Aromatic nitriles are typically stable solids. Protect from prolonged light exposure and moisture to maintain low water content and avoid slow hydrolysis under harsh conditions.
Handling:
Allow container to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
Minimize headspace humidity; promptly recap. For frequent access, consider aliquoting under dry nitrogen/argon.
Prepare stock solutions in anhydrous polar aprotic solvents (DMF, DMSO, DMAc, NMP) or warm chlorobenzene/toluene as required by solubility.
For moisture-sensitive reactions (e.g., LiAlH4 reductions), dry the solid under vacuum (ambient–40 °C) before use.
Typical laboratory stock concentrations: 0.05–0.5 M in DMF/DMSO (adjust as solubility dictates). Filter if particulates persist.
Freeze–thaw: Not applicable to solids; if stored as a solution, keep at low temperature (e.g., 2–8 °C) in tightly sealed vials and avoid repeated freeze–thaw by aliquoting.
Always refer to the product’s CoA and SDS for definitive stability and handling instructions for your specific lot.
Structure and Identity
2,5-Dimethylterephthalonitrile is an electron-deficient, para-dicyano-substituted benzene bearing two additional methyl substituents ortho to each nitrile.
Aromatic core: a 1,4-disubstituted benzene (para relationship between the two nitriles).
Functional groups: two nitrile groups (–C≡N) at positions 1 and 4; two methyl groups (–CH3) at positions 2 and 5.
Substitution pattern: 1,4-dicyano-2,5-dimethylbenzene; the nitriles are strong π-acceptors that render the ring electron poor; the methyl groups are weakly electron donating and increase hydrophobicity.
2D structure in words: a benzene ring with nitrile groups directly opposite each other across the ring; adjacent to each nitrile (ortho) sits a methyl substituent, giving a symmetric, cross-shaped substitution pattern.
Notes:
No stereocenters; molecule is achiral and conformationally rigid in the aromatic plane.
The two nitriles enable bifunctional derivatization (e.g., diamide, dicarboxylic acid, diamine, or ditetrazole formation).
Synthetic Utility
Functional group leverage:
Dual nitriles (–C≡N):
Hydrolysis (acid/base) → diamide/diacid series; entry to 2,5-dimethylterephthalic acid and esters (after alcoholysis).
Reduction → 2,5-dimethyl-1,4-bis(aminomethyl)benzene (primary diamine) for polymer and linker synthesis.
[3+2] Cycloaddition with azide → ditetrazoles, valuable as ligands or energetic fragments.
Benzylic methyls (2,5-positions):
Oxidation (e.g., KMnO4, RuO4, or catalytic aerobic oxidation) to carboxylates adds orthogonal functionality around the electron-poor ring.
Halogenation (NBS at benzylic positions) enables further substitution or cross-coupling at sidechains.
Strategic features (literature/general):
Symmetry: Para-dinitrile symmetry simplifies product distributions and facilitates step-economical difunctionalization.
Electronics: Strong –I/–M withdrawal by nitriles allows SNAr on appropriately activated systems downstream and stabilizes anionic intermediates during benzylic functionalization.
Materials relevance: Conversion to diacids/diesters or diamines yields monomers for rigid-rod polyesters/polyamides and donor–acceptor frameworks.
Retrosynthetic planning:
Target diamines/diacids can be traced back to this dinitrile via standard, scalable unit operations (hydrogenation, hydrolysis), offering robust disconnections for library or monomer synthesis.
Workup considerations:
Monitor for half-hydrolyzed amide intermediates; adjust stoichiometry/time to drive to the desired oxidation state. Crystallization often affords high purity due to planarity and strong intermolecular interactions of nitriles.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, or species specificity data are provided in the Product Data.
Preguntas frecuentes
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
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