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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
143.180 g/mol
XLogP3
2.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
1
Exact Mass
143.073 Da
Monoisotopic Mass
143.073 Da
Topological Polar Surface Area
23.800 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
176.000
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
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Recensioni
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Application Protocols
Not applicable as a biological assay reagent. No validated protocols for WB, IHC, IF, FC, or related applications are associated with this product.
Synthetic usage notes (general):
For handling, prepare stock solutions in a compatible dry organic solvent (e.g., toluene, THF, DCM, DMF) immediately before use when air/moisture sensitivity of the downstream reaction requires it.
Verify identity and purity by NMR/GC/LC prior to scale-up. Employ inert atmosphere techniques for air- or moisture-sensitive transformations involving this substrate.
Biological Roles
This product is a small-molecule aryl nitrile intended for chemical synthesis. It is not a biological buffer, nutrient, or biomacromolecule.
General/literature context (not specific to this item):
Aryl nitriles are common motifs in agrochemicals and discovery compounds due to the nitrile’s compact polarity and metabolic stability. The nitrile group can act as a weak hydrogen-bond acceptor and a dipolar moiety influencing binding in enzyme/receptor studies, but its presence here is as a synthetic handle rather than a defined bioactive feature.
Cyclopropyl substituents are often used in medicinal chemistry to modulate steric bulk, conformational restriction, and lipophilicity without greatly increasing molecular weight.
No claims are made regarding biological activity, safety in vivo, or clinical utility. For research use only, as stated in the product data.
Buffer Applications
Not typically applicable. 4-Cyclopropylbenzonitrile is a hydrophobic aryl nitrile building block and is not used to prepare aqueous buffer systems or as a buffering agent. For practical laboratory use, focus on the Synthetic Utility, Reaction & Applications, and Reaction Conditions sections.
Green Alternatives
While 4-cyclopropylbenzonitrile is a building block (not a solvent), greener choices can be applied to its synthesis and use.
Greener solvents for typical transformations (literature/general):
Replace chlorinated solvents (DCM/CHCl3) with:
• 2-MeTHF or CPME (ether class; lower peroxide tendency than THF for CPME; better lifecycle footprint than diethyl ether).
• Ethyl acetate or alcohols (when compatible).
• Toluene/anisol for high-temp couplings instead of NMP where feasible.
Polar aprotic replacements: Consider propylene carbonate or dimethyl sulfone in niche cases; or use DMF/DMAc with solvent recycling.
Process intensification and alternative technologies:
Micellar catalysis: Employ surfactant-water systems for certain couplings or reductions to suppress organic solvent use (reaction dependent).
Flow chemistry: Enhanced heat/mass transfer for exothermic reductions (e.g., DIBAL-H quench) or azide cycloadditions can increase safety and reduce solvent/energy footprints.
Catalytic reductions: Prefer catalytic hydrogenation over stoichiometric hydrides where compatible, minimizing waste.
Sourcing/route considerations (general):
If preparing in-house, choose cyanation routes that avoid toxic cyanide salts when possible (e.g., metal-catalyzed cyanation with safer CN surrogates) and employ robust containment/scrubbing where CN sources are unavoidable.
Trade-offs:
Greener solvents may affect rates/solubility; catalyst/ligand re-optimization is often required. Environmental improvements must be balanced against yield/selectivity and safety.
Pharmaceutical Uses
This product is supplied for research use only and is not an excipient or a finished pharmaceutical ingredient.
General/literature context (non-clinical):
Aryl nitriles are frequently employed as intermediates in pharmaceutical process development, enabling transformations to amides, acids, amines, or tetrazoles (useful as carboxylate bioisosteres). The para-cyclopropyl motif is a common steric and conformational element in discovery chemistry.
Potential roles in formulation are minimal; this compound is not a typical excipient. Any incorporation into drug substance synthesis would be as a chemical intermediate under GMP controls, which are beyond the scope of this catalog listing.
No therapeutic or clinical claims are made for this item.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (for general reference only; not specifications of this item):
Empirical formula (literature): C10H10N
Formula weight (calculated): ~144.19 g/mol
Physical state at ambient conditions: many para-substituted benzonitriles are crystalline solids or low-melting liquids; exact state for this item is not specified here.
Solubility profile: expected to be soluble in common organic solvents (e.g., dichloromethane, toluene, THF, ethyl acetate) and sparingly soluble in water (typical for aryl nitriles). Quantitative solubilities are not specified for this item.
Volatility: aryl nitriles generally exhibit moderate to low vapor pressure relative to small aliphatics; handle in a fume hood.
Spectroscopic handles: strong IR band for the nitrile stretch typically near 2220–2260 cm⁻¹ (literature). 1H/13C NMR consistent with para-disubstituted benzene and cyclopropyl resonances; 13C of CN near 115–120 ppm and of C≡N carbon near ~118–124 ppm (literature ranges).
Important: For authoritative physical property specifications (mp, bp, density, refractive index, UV cutoff, water content, metals, etc.), consult the CoA/Spec Sheet for this specific lot.
Quality and Grades
Grade/Purity (this item): Not specified for this item; refer to CoA/Spec Sheet.
Appearance (this item): Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades for small-molecule building blocks (general):
Research grade: Suitable for most synthetic applications; impurities are typically controlled to facilitate reactions and routine analytics (NMR/GC/HPLC). When not explicitly stated, assume normal organic impurity profiles and trace inorganics typical of fine chemicals.
High-purity/assay-specified: When assay is specified (e.g., ≥98%), such material supports sensitive transformations (e.g., cross-couplings) and reduces catalyst poisoning.
Low-UV/HPLC or LC-MS grade solvents vs. reagents: Not applicable here; this product is a building block rather than a chromatography solvent.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Aryl nitriles generally do not require inhibitors, and are typically stable under ambient storage in sealed containers.
Quality documentation:
Each lot should be verified against an internal specification. For exact acceptance criteria (assay method, residual solvents, inorganic residues, identity tests), consult the Aladdin CoA/Spec Sheet for SKU C1071973.
Recommendations:
For metal-catalyzed reactions, consider pre-checking by GC/HPLC and, if needed, performing a quick filtration through basic alumina to remove trace acidic impurities that may affect catalysts (general practice; not specific to this lot).
Reaction and Applications
4-Cyclopropylbenzonitrile is a versatile aryl nitrile building block that combines the directing/electron-withdrawing character of –C≡N with a strain-rich cyclopropyl substituent. Typical uses (literature/general):
Nitrile functional group interconversions:
• Hydrolysis to amides or carboxylic acids under acidic or basic conditions (R–C≡N → R–CONH2/CO2H).
• Reduction to primary amines (LiAlH4, BH3·THF, or catalytic hydrogenation) or to aldehydes (DIBAL-H, low temperature).
• Conversion to tetrazoles via [3+2] cycloaddition with azide (TMSN3 or NaN3/Lewis acid).
• Formation of amidines/imidates via Pinner or related chemistry.
Directed ortho-metallation: The nitrile can direct strong base metalation ortho to –C≡N (e.g., s-BuLi/TMEDA), enabling access to diversified ortho-functionalized analogs while the para cyclopropyl group remains intact under carefully controlled conditions.
Cross-couplings exploiting C–CN activation (nickel or palladium catalysis): Aryl nitriles can serve as electrophiles in couplings with boron, silicon, or Grignard partners under specialized ligand sets, enabling biaryl and aryl–alkenyl formations without halides (literature).
Cyclopropyl reactivity: The cyclopropyl ring can engage in radical-mediated ring-opening or serve as a conformational/steric modulator in medicinal chemistry SAR campaigns, while the nitrile acts as a handle for polarity tuning or downstream diversification.
Late-stage diversification: Robustness of –C≡N permits electrophilic aromatic substitutions or metal-catalyzed C–H functionalization at positions not deactivated beyond feasibility, subject to standard electronic/steric constraints.
Applications span discovery chemistry, analog synthesis, and materials-related motif introduction where a para-cyclopropyl aryl core and a convertible nitrile are desired.
Reaction Conditions
General literature guidance for common transformations of aryl nitriles (not item-specific specifications):
Hydrolysis to amide/acid:
• Acidic: conc. H2SO4 or HCl, 80–120 °C (amide) to reflux (acid). Extended times (hours) often required; water content controls selectivity.
• Basic: KOH/NaOH in aqueous alcohol or high-boiling glycols (e.g., ethylene glycol) at 120–180 °C, leading to carboxylate; acidic workup affords acid.
• Note: Cyclopropyl ring is generally stable to moderate acid/base but may ring-open under strongly acidic conditions—monitor by GC/LC.
Reduction:
• To primary amine: LiAlH4 in THF/Et2O, 0 °C → reflux, 2–16 h; or catalytic hydrogenation (Raney Ni, Pd/C, 1–10 bar H2) in EtOH/AcOH at rt–60 °C.
• To aldehyde: DIBAL-H (1–2 equiv) in toluene/THF at −78 to −20 °C, then careful quench at low temp to minimize over-reduction.
Tetrazole formation:
• TMSN3 (excess) with Lewis acids (ZnBr2, AlCl3) in toluene/CH3CN at 60–110 °C; or NaN3 with Zn2+ salts in DMF at 80–120 °C. Handle azides with rigorous safety protocols.
Ortho-lithiation:
• s-BuLi (1.1–1.5 equiv) with TMEDA in THF at −78 °C, then trap with electrophiles (B(OR)3, D2O, CO2). Quench at low temp to avoid rearrangements.
C–CN activation/cross-coupling:
• Ni(cod)2 (5–10 mol%), bidentate phosphine or NHC ligands, base (e.g., iPr2NEt), in dioxane/THF/toluene, 80–130 °C, 6–24 h, coupling with B2pin2 (borylation) or organozincs. Ligand/catalyst tuning is crucial.
Yields and exact parameters vary by substrate and setup; consult primary literature and perform small-scale scouting runs.
Safety and Handling
Safety classification for this catalog item:
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/general):
Hazards: Aromatic nitriles can be harmful if swallowed, inhaled, or absorbed through skin. While benzonitrile derivatives are less prone than aliphatic nitriles to liberate hydrogen cyanide under neutral conditions, decomposition in strong acids/bases or at high temperature can generate toxic species. Avoid aerosol formation.
Engineering controls: Use in a certified chemical fume hood. Provide local exhaust during heating or reactions.
PPE: Lab coat, safety glasses or splash goggles, and nitrile gloves (change regularly). Consider double-gloving for extended contact or solvent work.
Incompatibilities: Strong oxidizers. Hydrolysis under strong acidic or basic conditions may occur; avoid prolonged exposure to concentrated acids/bases unless intended for reaction. Combustible—keep away from ignition sources.
First-aid overview:
• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin contact: Remove contaminated clothing; wash with soap and water.
• Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Spill/Fire: Absorb small spills with inert material; for fire use dry chemical, CO2, or foam. Thermal decomposition may emit irritating/toxic fumes.
Always defer to the Aladdin Scientific SDS for definitive hazard and response information.
Solvent Selection
This product is an aryl nitrile building block rather than a solvent. Solvent selection relates to its use in synthesis and analysis.
Polarity class (analyte): Moderately nonpolar/aprotic; aromatic with a polar nitrile functionality. Exhibits good solubility in many organic solvents.
Common solvents for handling/dissolution (general guidance):
• Dichloromethane (DCM), chloroform: rapid dissolution; suitable for extractions and reactions at 0–40 °C.
• Toluene, xylene: good for higher-temperature reactions and metal-catalyzed couplings.
• THF, 2-MeTHF, MTBE, EtOAc: useful in organometallic and nucleophilic reactions; 2-MeTHF is a greener alternative to THF.
• DMF, DMAc, NMP, DMSO: maximize solubility for polar transformations (e.g., SNAr, Ni-catalyzed C–CN activation).
Aqueous media: Aryl nitriles are typically poorly soluble in water; phase-transfer or micellar conditions can sometimes be employed for greener processes (literature), but performance is reaction-specific.
Analytical solvents: For NMR, CDCl3 or DMSO-d6 generally provide clean spectra for aryl nitriles; verify solubility prior to preparation.
Comparison notes (general):
Choose aprotic, non-nucleophilic solvents for reactions sensitive to nucleophiles (e.g., DIBAL-H reductions).
For high-temperature couplings, toluene or anisole can offer higher reflux temps vs THF/EtOAc.
For greener profiles, consider 2-MeTHF, EtOAc, propylene carbonate, or cyclopentyl methyl ether (CPME) where compatible with the transformation.
Storage and Reconstitution
Storage conditions (this item): Room temperature (as provided in Product Data). Store tightly closed in the original container. Protect from excessive heat and direct sunlight.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Stability: Aryl nitriles are typically stable under ambient lab conditions. Avoid prolonged exposure to strong acids/bases unless for intended reactions.
Moisture/air sensitivity: Generally not moisture sensitive; however, keep container tightly sealed to prevent contamination and solvent loss if supplied as a liquid.
Reconstitution/Preparation for use:
• If supplied as a solid: Dissolve in an appropriate organic solvent (e.g., DCM, toluene, THF, EtOAc, DMF) to prepare stock solutions at desired concentrations.
• If supplied as a liquid: Use neat or dilute into a compatible anhydrous solvent as required by the reaction.
• Filter through a PTFE syringe filter (0.2–0.45 µm) if particulates are observed.
Freeze–thaw guidance: Not typically applicable. Avoid unnecessary temperature cycling; store at consistent room temperature.
Documentation: For lot-specific stability, packaging type, and any additional handling instructions, consult the Aladdin Scientific CoA/Spec Sheet.
Research Use Only: As stated, this material is supplied strictly for research and laboratory use.
Structure and Identity
Brief description: 4-Cyclopropylbenzonitrile is a para-substituted aryl nitrile featuring a benzene ring bearing a nitrile (–C≡N) and a cyclopropyl group in the 1,4-relationship.
Product Name (catalog): 4-Cyclopropylbenzonitrile
CAS: 1126-27-8
CID: 11332535
SKU: C1071973
InChIKey (as provided in Product Data): 123483
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Common/literature SMILES (for reference): N#Cc1ccc(cc1)C2CC2
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Typical/literature formula: C10H10N
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Calculated from literature formula (C10H10N): ~144.19 g/mol
Structural features (general/literature description):
Functional groups: one aromatic nitrile (sp-hybridized carbon of –C≡N), one cyclopropyl alkyl substituent.
Ring systems: one benzene ring (planar, conjugated) and one cyclopropane ring (strained three-membered ring).
Substitution pattern: para (1,4) relationship between –C≡N and –cyclopropyl, minimizing steric interactions and enabling conjugative/inductive electronic effects across the ring.
Stereochemistry: none (achiral). 2D depiction would show a benzene ring with –C≡N at C1 and –C3H5 (cyclopropyl) at C4.
Notes: Identity values specifically tied to this catalog item that are not listed above should be confirmed in the item’s CoA/Spec Sheet.
Synthetic Utility
Key functional handles and strategies (literature/general):
Nitrile as a convertible group:
• Hydrolysis sequence: –C≡N → amide (controlled hydrolysis) → acid (harsher conditions).
• Reductions: to primary amine (LiAlH4, borane, catalytic H2) or to aldehyde (DIBAL-H, −78 to −20 °C).
• Heterocycle formation: tetrazoles via azide [3+2] cycloaddition; imidates/amidines via Pinner/Beckmann-adjacent chemistries (as applicable to nitriles).
Directing effects: The –C≡N group is a strong ortho-director for metalation, enabling introduction of electrophiles (D, halogens, formyl, boryl) at the ortho positions. Subsequent functional group manipulations can be sequenced to diversify the scaffold.
Cross-coupling via C–CN activation: Under Ni/Pd catalysis with tailored ligands, aryl nitriles can be transformed into aryl boronates (borylation), silanes, stannanes, or engaged directly in Suzuki/Negishi-type couplings—useful when halide analogs are unavailable.
Cyclopropyl chemistry: The cyclopropyl ring can be preserved as a compact hydrophobic substituent or opened under radical/acidic conditions to access propyl/allylic variants, offering late-stage scaffold adjustment.
Protecting-group orthogonality: The nitrile often survives conditions that would cleave esters, carbamates, or silyl ethers, enabling it to act as a polarity handle through multistep sequences.
Retrosynthetic value: 4-Cyclopropylbenzonitrile can trace back to para-substituted anilines/acids via Sandmeyer-type cyanation or to para-halobenzenes via metal-catalyzed cyanation; conversely, it can branch forward to amides, acids, primary amines, or tetrazoles for library diversification.
Target Specificity
Not applicable. This product is a small-molecule building block and not a biological targeting reagent (e.g., antibody, ligand standard). No antigen, clone, isotype, or species reactivity information applies.
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