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
Not available
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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Recensioni
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Application Protocols
Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic usage, see Reaction Conditions and Application notes in Reaction & Applications.
Biological Roles
This compound is a synthetic aromatic trinitrile and is not known to have endogenous biological roles.
Item-specific note
Research Use: For research use only (per Product Data). No medical or clinical use is intended or implied.
Literature/general context
Not a natural metabolite; primarily used as a chemical building block and materials precursor.
Derivatives (e.g., triacids, triamides, tritetrazoles) can interact with metal ions and assemble into supramolecular architectures relevant to biomimetic materials research, but the parent trinitrile itself is generally biologically inert under physiological conditions.
Aromatic nitriles exhibit low aqueous solubility and limited bioavailability; hydrolysis to amide/acid derivatives increases polarity but is typically slow without catalysts/harsh conditions.
Practical implication for life-science labs
Any biological testing should account for low water solubility; DMSO stock solutions and careful vehicle controls are standard practice if exploratory assays are attempted. Ensure compliance with institutional approvals and handle strictly as a research chemical.
Buffer Applications
Not typically applicable. 1,3,5-Benzenetricarbonitrile is a neutral, weakly basic nitrile-bearing aromatic solid and does not serve as a buffering agent over biological pH ranges. For work involving this compound in aqueous systems, see Solvent Selection for cosolvent strategies and Reaction & Applications for hydrolysis or derivatization to more polar species.
Green Alternatives
Greener choices are mostly about solvent/catalyst selection and process intensification; the substrate itself is fixed.
Solvent alternatives (literature guidance)
Replace DMF/NMP/DMAc with acetonitrile, propylene carbonate, 2-MeTHF, or water/co-solvent systems when chemistry allows.
For hydrolysis, consider water-lean systems (water/EtOH, water/AcOH) and avoid halogenated solvents.
For Pinner reactions, use ethanol instead of methanol where feasible and recover HCl via gas scrubbing.
Catalysis and energy
Employ heterogeneous catalysts (Pd/C, Raney Ni) under mild H2 pressures to reduce energy demand; explore transfer hydrogenation (iPrOH) to avoid compressed gas where appropriate.
Use phase-transfer catalysis or microwaves to shorten cycloadditions/hydrolyses, reducing solvent volumes/time.
Waste minimization
Design for high atom economy routes: direct tetrazole formation from nitriles with NaN3/Zn(OTf)2 or Cu catalysts (caution: energetic products; manage safely).
Implement crystallization-driven purifications to limit chromatographic solvent waste.
Comparison (general, not item-specific)
DMF vs MeCN: MeCN has lower toxicity profile and easier recovery; solvency is somewhat lower, so higher temperature or volume may be required.
DCM vs 2-MeTHF: 2-MeTHF is bio-derived and less chlorinated-waste intensive; boiling point is higher, aiding reactions but complicating solvent removal.
H2 gas vs transfer hydrogenation: Eliminates cylinder handling at the cost of sacrificial alcohol and potentially longer times.
Pharmaceutical Uses
Item-specific
No pharmacopeial grade or excipient status is provided for this item; refer to CoA/Spec Sheet.
General, non-clinical context
Role: Potential intermediate in the synthesis of C3-symmetric scaffolds (e.g., tricarboxamides, triamidines) that can be investigated as ligands, materials, or specialty auxiliaries in pharmaceutical process development.
Manufacturing considerations: If used as a process intermediate, attention should be paid to residual nitrile content, aromatic impurities, and solvent residues per ICH Q3A/Q3C guidelines (project-specific).
Formulation: The parent trinitrile is not used as an excipient; water insolubility and strong odorless nitrile functionality limit direct formulation use.
No therapeutic or clinical claims are made. This product is supplied strictly for research and laboratory use.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for reference only; not item specifications)
Physical state: Typically a crystalline solid (literature)
Melting point: ~198–201 °C (literature)
Boiling point: High; may decompose before boiling at atmospheric pressure (literature)
Solubility: Sparingly soluble in water; soluble to miscible in polar aprotic organic solvents (e.g., acetonitrile, DMF, DMSO), moderately soluble in chlorinated solvents and hot alcohols (literature)
Density: Not widely reported; consult primary data if needed (literature)
LogP (octanol/water): Expected low-to-moderate positive value due to aromatic core and polar nitriles; specific value not uniformly reported (literature)
pKa: Not applicable (no titratable protons on the neutral molecule); conjugate acids of nitriles are very strong acids and not typically measured in water (literature)
UV–Vis: π→π* absorption in the UV region typical of substituted benzenes; ε increases with conjugated nitriles (literature)
Practical notes (general)
The three –C≡N groups increase crystal lattice energy; hot solvents or high-boiling dipolar aprotics often required for dissolution.
Hygroscopicity: Generally low for aromatic nitriles; protect from moisture for hydrolysis-sensitive applications (literature).
Quality and Grades
Item-specific
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general information for context)
Research/technical grade: Suitable for most synthetic and materials applications where trace UV impurities and metal content are not critical.
High-purity or “electronic/photonic” grades (when available): Targeted low metal content and low fluorescence/UV background for optoelectronic or photophysical studies.
HPLC or LC–MS suitability: When relevant, low non-volatile residue and minimal UV-absorbing impurities are preferred; check UV cutoff/trace-impurity data on the CoA when performing quantitative spectroscopy.
Quality considerations specific to trinitriles (general)
Key impurities: Residual monocyano/dicyano benzenes, hydrolysis products (amides/acids), and polymeric discolorants. These can influence crystallization behavior and downstream coupling efficiencies.
Verification: 1H/13C NMR (aromatic and nitrile carbons), IR (sharp νC≡N ~2230–2260 cm⁻¹), HRMS, and HPLC/GC purity are typical. Elemental analysis can be diagnostic due to high N content.
Metal content: If using in catalysis or as a MOF/COF node, trace metal levels may matter; request ICP data if needed.
Documentation
Always consult the lot-specific CoA/SDS for exact assay, residual solvents, water content, and any stabilizers for this item.
Reaction and Applications
1,3,5-Benzenetricarbonitrile is a versatile C3-symmetric hub for assembling tripodal molecules, porous polymers, and advanced materials.
Transformation families (literature)
Hydrolysis: Controlled conversion of –C≡N to amides (partial) or carboxylic acids (complete). Acidic (e.g., H2SO4, HCl) or basic (NaOH/KOH) conditions; stepwise hydrolysis enables tri-amide/tri-acid libraries.
Reduction: Catalytic hydrogenation (Pd/C, Pt/C, Raney Ni) or hydride reagents to give tris(aminomethyl)benzene derivatives; borane can yield primary amines via imidate intermediates.
Pinner/Amidine formation: Treatment with dry HCl in alcohol forms imidate esters; subsequent amine addition affords tris-amidines—useful for polyelectrolytes and ligand platforms.
[3+2] Cycloadditions: Sodium azide in polar aprotic solvents forms 1,3,5-tris(tetrazolyl)benzenes—energetic ligands and MOF linkers.
Metal–ligand assembly: Nitriles coordinate weakly to many metals, aiding crystal engineering; hydrolyzed/amidated derivatives form stronger chelating nodes.
Materials and synthetic uses (literature)
COF/MOF linkers: The C3 symmetry enables 2D/3D network formation after conversion to carboxylates/tetrazolates.
Crosslinkers/monomers: Tri-functional nitrile enables post-polymerization modification and formation of star-shaped macromolecules.
Electronic materials: Electron-poor aromatic core participates in charge-transport tuning in donor–acceptor frameworks.
Practical notes
The aromatic ring is deactivated; electrophilic aromatic substitution is suppressed. Nucleophilic aromatic substitution is favored at positions activated by the nitriles (when suitable leaving groups are present).
Ensure adequate dissolution (DMF/DMSO/MeCN, heat). For hydrogenations, remove coordinating solvents and filter catalysts hot to avoid crystallization on the frit.
Reaction Conditions
General, literature-based guidance (not item-specific specifications). Optimize per your system and consult primary references.
Hydrolysis of –C≡N
Acidic: Reflux in 6–12 M HCl or concentrated H2SO4/AcOH mixtures for 6–24 h to drive toward tri-acid; shorter times or milder acids favor amides. Workup via dilution, neutralization, and crystallization.
Basic: Aqueous NaOH/KOH (2–6 M) in water/EtOH or water/DMF at 80–120 °C. Prolonged heating can over-hydrolyze; monitor by IR (loss of νC≡N) or HPLC.
Reduction to tris(aminomethyl) derivative
Catalytic hydrogenation: 10 wt% Pd/C (5–20 mol% cat. relative to nitrile functions), EtOH or AcOH, 3–10 bar H2, 25–80 °C, 4–18 h. Raney Ni offers economical alternatives; add base if ammonium salts form.
Borane or LiAlH4: THF/ether, 0–25 °C to reflux; careful quench protocols required.
Pinner/Amidine formation
Dry HCl in MeOH/EtOH at 0–25 °C to form imidate salts (2–12 h), followed by amine (2–5 equiv) to furnish amidines at 25–60 °C.
Tetrazole formation
NaN3 (3–6 equiv per nitrile) with Zn(OTf)2 or Lewis acid in DMF/DMSO, 80–130 °C, 6–24 h; aqueous workup and salting-out crystallization.
Crystallization/purification
Recrystallize from hot acetonitrile, acetone, or EtOH/MeCN mixtures. Column chromatography is rarely needed for highly crystalline tri-products.
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General safety (literature; consult SDS for authoritative guidance)
Likely hazards: May cause irritation to eyes/skin/respiratory tract. As with many nitriles, strong acid/base hydrolysis can release ammonia or, under certain conditions, traces of hydrogen cyanide—avoid heating with strong acids/bases in confined systems.
PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
Incompatibilities: Strong oxidizers (general precaution); vigorous hydrolysis in concentrated mineral acids or strong bases; avoid reactive metals with strongly coordinating nitriles in the presence of catalysts.
Thermal stability: Aromatic nitriles are thermally robust but can decompose upon prolonged heating at elevated temperature.
First aid (overview): Move to fresh air if inhaled; rinse skin/eyes with water for ≥15 minutes upon contact; seek medical attention if symptoms persist. If ingested, rinse mouth—do not induce vomiting; obtain medical attention.
Fire response: Use dry chemical, CO2, alcohol-resistant foam. Combustion may produce NOx and CO/CO2. Firefighters should wear self-contained breathing apparatus.
Handling tips
Avoid dust generation; use weigh boats and antistatic measures.
Store tightly closed at room temperature, dry, and away from strong acids/bases (per Product Data storage and general practice).
Solvent Selection
This product is a solid aromatic trinitrile; solvent choice is driven by dissolution needs and reaction pathway (hydrolysis, reduction, Pinner, [3+2] cycloadditions).
Good solvents: DMF, DMAc, DMSO, NMP, acetonitrile; hot ethanol/isopropanol; chlorinated solvents (DCM/CHCl3) to a lesser extent.
Poor solvents: Water (sparingly soluble); nonpolar hydrocarbons unless heated with cosolvents.
Selection by transformation (general guidance)
Hydrolysis to amide/acid: Mixed aqueous mineral acid with a polar aprotic cosolvent (e.g., AcOH/H2O or H2SO4/AcOH; or NaOH/H2O/EtOH) to manage solubility.
Pinner reaction to imidates/amidines: Anhydrous alcohol (MeOH, EtOH) saturated with dry HCl under cooling; subsequent aminolysis in the same solvent or a polar aprotic.
Hydrogenation to tris(aminomethyl)benzene: Alcohols (EtOH, iPrOH) or acetic acid with Pd/C, Pt/C, or Raney Ni; DMF can coordinate catalysts—avoid if activity is suppressed.
[3+2] Azide–nitrile to tetrazoles: DMF, DMSO, or ionic liquids to dissolve both azide salts and substrate; water/EtOH mixtures if phase-transfer catalysis is employed.
Practical tips
Begin with 5–20 mL solvent per gram and heat to dissolve; cool slowly for recrystallization.
For greener profiles, consider MeCN or 2-MeTHF blends over DMF/NMP when feasible.
Storage and Reconstitution
Item-specific
Storage Conditions: Room temperature (per Product Data). Store tightly closed in a dry place.
Shipped In: Normal (per Product Data).
General handling of aromatic trinitriles (literature)
Protect from moisture if long-term storage is intended, especially if subsequent reactions are hydrolysis-sensitive. Desiccation (P2O5, silica gel) is beneficial.
Avoid prolonged exposure to strong acids/bases; keep away from oxidizers.
Reconstitution/solution preparation (general guidance; not a specification)
Prepare stock solutions in polar aprotic solvents (DMF, DMSO, acetonitrile) at 10–100 mg/mL depending on solubility and application; warm gently (40–60 °C) and sonicate to accelerate dissolution.
For aqueous work, use cosolvents (≤1–5% DMSO or MeCN in water) and vigorous stirring; note that precipitation may occur upon dilution.
Filter warm through PTFE (0.2–0.45 µm) if particulate persists; avoid nylon filters for strongly acidic/basic solutions.
Stability
Solid state: Typically stable for years at ambient conditions when dry and protected from light.
Solution: Most stable in anhydrous, neutral aprotic solvents; hydrolyzes slowly in hot aqueous acidic/basic media—prepare fresh solutions for sensitive transformations.
Structure and Identity
A rigid C3‑symmetric aromatic trinitrile used as a trifunctional electrophilic building block.
Item-specific (from Product Data)
SKU: B152001
Product Name: 1,3,5-Benzenetricarbonitrile
CAS: 10365-94-3
CID: 82587
InChIKey: 335296 (as provided)
Storage: Room temperature; shipped under normal conditions
Literature/computed (general reference values; not item specifications)
Core: Planar benzene ring with three cyano (–C≡N) substituents in a 1,3,5 (meta,meta,meta) arrangement, imparting D3h symmetry in an idealized sense.
Functional groups: Three strongly electron-withdrawing nitriles conjugated to an aromatic ring; no stereocenters.
Electronic characteristics: The ring is deactivated toward electrophilic aromatic substitution and activated toward nucleophilic aromatic substitution at positions ortho/para to –C≡N. Each nitrile carbon is electrophilic and participates in addition, reduction, and hydrolysis pathways.
2D description: A hexagonal aromatic ring bearing three evenly spaced –C≡N groups at alternating vertices (positions 1,3,5), generating a trigonal, star-like topology useful for assembling C3-symmetric scaffolds (COFs/MOF linkers, tripodal ligands).
Synthetic Utility
Functional group reactivity (literature)
Nitrile carbon is electrophilic: susceptible to nucleophilic addition (to give imidates, amidines) and hydrolysis (to amide/acid).
Reduction to primary amines furnishes 1,3,5-tris(aminomethyl)benzene, a versatile tripodal amine core for ligands, crosslinkers, and COF precursors.
[3+2] Cycloaddition with azide yields tritetrazolylbenzenes—excellent polydentate linkers and energetic anion receptors.
Aromatic platform behavior
The C3 symmetry is ideal for star-shaped architectures; the ring is strongly deactivated toward electrophilic substitution but amenable to nucleophilic aromatic substitution when suitably activated/leaving groups are present.
Conjugation with three nitriles lowers LUMO, supporting donor–acceptor designs in organic electronics.
Retrosynthetic value
Serves as a convergent node enabling late-stage diversification at three equivalent sites, simplifying library synthesis (tri-amides, tri-esters, tri-guanidines, tri-ureas via downstream transformations).
Practical synthesis notes
Multisite transformations benefit from excess reagent and controlled temperature to maintain site equivalence.
Sequential selectivity (mono-/di-/tri-functionalization) can be tuned via stoichiometry and solvent choice, enabling stepwise diversification when needed.
Target Specificity
Not applicable. This product is a small-molecule trinitrile, not an antibody, enzyme, or affinity reagent. No antigen/epitope specificity, clone, isotype, or species reactivity applies.
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