This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
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
265.260 g/mol
XLogP3
2.700
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Exact Mass
265.074 Da
Monoisotopic Mass
265.074 Da
Topological Polar Surface Area
67.200 Ų
Heavy Atom Count
20
Formal Charge
0
Complexity
423.000
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
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No assay-specific, validated application protocols are provided for this chemical intermediate.
If using as a substrate or intermediate, follow standard organic synthesis protocols relevant to the planned transformation (see Reaction Conditions and Synthetic Utility tabs).
For analytical characterization, typical methods include 1H/13C NMR (DMSO-d6, CDCl3, acetone-d6), IR (strong C=O ~1650–1680 cm−1; C≡N ~2220–2260 cm−1; ester C=O ~1730–1760 cm−1; literature), HPLC/LC–MS for purity and identity, and HRMS.
For handling in bioassays (if applicable to your research), prepare DMSO or MeCN stock solutions (e.g., 10–100 mM), filter if necessary (PTFE syringe filters), and dilute into buffered media ensuring final organic cosolvent ≤1–2% v/v to maintain biological compatibility.
Note: Parameters such as water content, residual solvents, and exact purity are lot-dependent and not specified for this item; consult the CoA.
Biological Roles
This product is a synthetic, non-natural small molecule designed as a chemical intermediate. It has no known endogenous biological role.
Endogenous occurrence: none expected; benzophenone-based, nitrile-containing aromatic esters are not common metabolites.
Biochemical interactions (general observations): aromatic ketones can engage in noncovalent interactions (π–π, hydrophobic) with proteins and membranes in vitro; nitriles are generally metabolically stable but can undergo biotransformation (hydrolysis/reduction) in some enzymatic systems (literature). These are context-dependent and not predictive of biological activity.
Photophysical considerations: benzophenone chromophores are triplet sensitizers; in biochemical assays, this can lead to photoinduced interactions or ROS generation under UV irradiation. Avoid unintended UV exposure if biological matrices are present.
Use context reminder: As stated in the Product Data, this material is for research use only. It is not intended for in vivo administration, diagnostic procedures, or therapeutic applications. Any biological testing should be performed under appropriate institutional approvals and safety reviews.
If biological compatibility or off-target interactions are relevant to your project (e.g., probe development), determine empirical properties such as logP, solubility in assay buffers (via cosolvents), and any photochemical reactivity under assay illumination conditions. No pharmacological targets are specified for this item.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biological or analytical buffers.
Aryl ketone/ester/nitrile scaffolds lack acid/base conjugate pairs suitable for maintaining pH in aqueous systems.
If used in biochemical assays, dissolution generally requires an organic cosolvent (e.g., DMSO, MeCN, EtOH) followed by dilution into buffer; ensure the final cosolvent content is compatible with the biological system.
For buffer preparation guidance, refer instead to dedicated buffers (e.g., phosphate, Tris, HEPES, acetate).
Green Alternatives
While the compound itself is a specialized intermediate, greener choices can be made in solvents and reagents used with it.
Replace dichloromethane/chloroform with ethyl acetate, 2-MeTHF, CPME, or toluene when solubility and selectivity allow.
Favor acetonitrile or EtOAc over DMF/DMSO when elevated temperature is not required, to ease workup and reduce EHS concerns.
For extractions and chromatography, consider heptane/EtOAc or cyclohexane/EtOAc systems instead of hexane/DCM.
Comparison snapshot (typical):
DCM vs EtOAc: EtOAc has lower toxicity, is biodegradable, and is derived from bio-ethanol/acetic acid; DCM offers higher density and volatility but presents higher environmental/health concerns.
THF vs 2-MeTHF: 2-MeTHF is biorenewable, forms fewer peroxides, and improves phase separation; THF is fully miscible with water and often requires careful peroxide control.
DMF/DMSO vs MeCN/CPME: MeCN and CPME are easier to remove and generally present lower worker exposure concerns than DMF; CPME is hydrophobic and supports water-tolerant catalysis.
Reagent alternatives (general):
Base-promoted deacetylation: use K2CO3 in MeOH/EtOH (catalytic) instead of strong bases (NaOMe/NaOH) to reduce waste and hazard.
Nitrile hydrolysis: enzymatic nitrilases or milder aqueous conditions under phase-transfer catalysis can replace strong mineral acids or bases for some substrates (evaluate case-by-case).
Reductions: consider catalytic hydrogenation (H2, Pd/C) under controlled conditions rather than stoichiometric metal hydrides where chemoselectivity permits.
Process considerations:
Minimize high-temperature steps to reduce energy demand and ester hydrolysis byproducts.
Employ solvent recycling and in-process controls (IPC) to optimize E-factors.
Pharmaceutical Uses
No pharmacopeial status or excipient role is provided for this compound; it is intended for research use as a synthetic intermediate.
Role in drug discovery/process chemistry (general):
As a multifunctional benzophenone derivative, it can serve as a late-stage intermediate or impurity reference in medicinal chemistry programs exploring aryl ketone motifs.
The acetoxy group is a removable protecting group for a salicyl-type phenol, facilitating analog synthesis around 2-hydroxybenzophenone cores common in kinase, protease, or photochemical probe scaffolds (literature context, non-clinical).
The nitrile offers a compact bioisostere for amide/carbonyl functionality and can be diversified into amines/amides/acids during SAR exploration.
Regulatory note: Not an approved API or excipient. No USP/Ph.Eur. monographs are implied. Any use in GMP settings would require independent qualification, impurity profiling, and residual solvent/toxicology assessments.
Formulation considerations (if handled as a reference material or intermediate): low aqueous solubility suggests use of organic vehicles or solid dispersion for analytics. Photostability testing may be warranted due to the benzophenone chromophore.
Always avoid clinical or diagnostic use. Restrict handling to R&D environments with appropriate SOPs and change controls.
Physical Properties
Item-specific specifications are not provided in the Product Data. The following are general/literature expectations for compounds of this structural class; verify with the CoA/SDS before use.
Appearance: Not specified for this item; refer to CoA/Spec Sheet. Aromatic benzophenone derivatives are typically off-white to pale solids (literature).
Molecular weight: ~265.27 g/mol (computed from C16H11NO3; literature).
Melting point: Not specified for this item; refer to CoA/Spec Sheet. Many substituted benzophenones melt in the 70–170 °C range (literature, wide variation by substitution).
Boiling point: Not typically distilled due to thermal sensitivity of aryl esters; BP not commonly reported (literature).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable to solids; if oil, not specified for this item.
Solubility (literature/typical):
Water: expected to be very low due to aromaticity and limited H-bond donors.
Organic solvents: expected to be soluble in ethyl acetate, dichloromethane, chloroform, THF, acetone, and acetonitrile; moderate in toluene; highly soluble in DMSO/DMF.
LogP: likely moderate (typical for benzophenone derivatives; literature trend). Not specified for this item.
UV-Vis: benzophenone chromophore typically absorbs in near-UV (ca. 240–260 nm, 320–350 nm bands; literature). Not specified for this item; refer to CoA if UV cutoff matters.
Note: The aryl ester can undergo thermal or hydrolytic cleavage; avoid prolonged heating above its decomposition onset (consult SDS/CoA).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. In the absence of a declared grade, users should confirm assay, residual solvents, and impurity profile on the lot-specific Certificate of Analysis.
Context on common grades (general guidance):
Research/Technical grade: suitable for most synthetic applications; assay typically >95%, but exact threshold is lot-dependent. Verify if trace metals, water, or UV absorbance are critical to your method.
HPLC grade (if applicable, not specified here): optimized for low UV absorbance/background; typically used for chromatographic mobile phases, which is not the primary use case for this solid reagent.
Low-water/anhydrous specifications (not specified here): would be relevant if base-sensitive steps (to avoid ester hydrolysis) are planned.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet. Aromatic esters typically do not require stabilizers, but inert packaging and desiccation improve shelf life.
What to check on receipt:
Appearance, melting point (if provided), and NMR consistency with a reference spectrum.
Purity assay (e.g., HPLC/GC) and residual solvents.
Peroxide content is not relevant to this class; aryl esters/ketones are not known peroxide formers.
Regulatory/usage note: Research use only (as stated in Product Data). Not for human or veterinary use.
Reaction and Applications
As a multifunctional benzophenone derivative, 2-acetoxy-3′-cyanobenzophenone serves as a versatile intermediate where orthogonal transformations enable route diversification.
Protective-group chemistry: the 2-acetoxy unit is a removable protecting group for an ortho-phenol. Mild deprotection under basic (Na2CO3, K2CO3, NaOMe) or acidic (AcOH, HCl) conditions regenerates the phenol, enabling subsequent etherification, esterification, or intramolecular cyclizations.
Carbonyl chemistry: selective reduction of the benzophenone carbonyl to secondary alcohols (NaBH4, DIBAL-H, catalytic hydrogenation) while retaining the nitrile and ester under carefully chosen conditions; or conversion to imines/oximes and subsequent transformations (e.g., Beckmann rearrangement on oximes; literature precedent for benzophenone scaffolds).
Nitrile transformations: hydrolysis to amide/carboxylic acid (acidic or basic; stepwise), partial reduction to imine/amine (Raney Ni/H2, LiAlH4, or catalytic hydrogenation), or addition of organometallics to form ketimines/tertiary alcohols upon workup.
Directed metalation/cross-coupling: although not halogenated, the nitrile and carbonyl groups are strong directors for ortho-lithiation on their respective rings (via TMP/buLi at low T), permitting subsequent electrophile trapping and, after halogenation, Pd-catalyzed cross-couplings.
Intramolecular assembly: after deacetylation to the 2-hydroxybenzophenone (salicylophenone), the ortho-phenol can undergo O-alkylation/acylation, or be leveraged in chelation-controlled reactions and photoactive benzophenone derivatives for materials or photochemistry research.
Practical tips:
Sequence planning: perform base- or acid-sensitive steps with awareness of ester lability; nitrile is robust to many conditions but sensitive to strong acids/bases at high temperature.
Protecting-group orthogonality: if phenol must remain masked during carbonyl/nitrile chemistry, avoid nucleophiles that would saponify the acetate.
Photochemistry: the benzophenone chromophore can engage in triplet-sensitized processes; verify if the acetoxy and nitrile substituents alter triplet yields for your application (literature characterization recommended).
Reaction Conditions
The following condition ranges are general literature guidance for functional groups present in 2-acetoxy-3′-cyanobenzophenone. Optimize for your substrate and scale.
Deacetylation (unmask phenol):
Basic: K2CO3 (1–2 equiv) in MeOH or MeOH/THF (0.05–0.2 M), 20–40 °C, 0.5–4 h; monitor by TLC/HPLC. NaOMe (0.1–0.5 M in MeOH) affords faster rates but higher risk of side reactions.
Acidic: AcOH–H2O (9:1) or catalytic H2SO4 in MeOH, 25–50 °C, 1–6 h. Avoid strong mineral acids at high temperature to protect the nitrile.
Carbonyl reduction (to benzhydrol):
NaBH4 (1.5–3 equiv) in MeOH, EtOH, or THF/MeOH at 0–25 °C, 0.5–2 h. Nitrile and ester typically remain intact under mild conditions.
Catalytic hydrogenation: H2 (1–5 bar), Pd/C (5–10 wt%), EtOAc/EtOH, 20–25 °C, 2–8 h; watch for potential nitrile reduction at elevated pressure/temperature.
Nitrile hydrolysis:
Acidic: H2SO4 or HCl (2–6 M) in aqueous dioxane/MeCN, 70–110 °C, 4–24 h → amide/acid depending on time and water content.
Basic: NaOH or KOH (2–5 equiv) in EtOH/H2O or DMSO/H2O, 60–110 °C, 4–24 h; ester saponification will co-occur; stage transformations accordingly.
Nitrile reduction:
LiAlH4 (2–4 equiv) in THF, 0–25 °C to reflux, 2–6 h → primary amine; may reduce the ketone—protect or sequence accordingly.
Catalytic hydrogenation: H2 (10–30 bar), Raney Ni or Pd/C, MeOH/EtOH, 25–80 °C, 4–24 h; monitor to avoid over-reduction.
Ortho-lithiation (directed by nitrile or carbonyl):
s-BuLi or n-BuLi with TMPH (LiTMP) in THF at −78 to −40 °C, 0.5–2 h; quench with electrophiles (I2, CO2, MeI). Ensure ester stability under base.
Typical workup:
Quench basic reactions with NH4Cl or AcOH; extract with EtOAc/DCM. Dry over Na2SO4/MgSO4; avoid prolonged basic aqueous exposure to preserve ester.
Yields: strongly substrate- and condition-dependent; consult primary literature for close analogs.
Safety and Handling
Hazard classification and pictograms are not provided in the Product Data. Treat this compound as a laboratory chemical with unknown acute hazards until SDS review.
GHS classification, signal word, H-statements, and pictograms: Not specified for this item; refer to the SDS for authoritative information.
General handling guidance (good laboratory practice):
Likely hazards (based on functional groups, literature): irritant to skin/eyes/respiratory tract; harmful if swallowed. Aryl nitriles and aromatic ketones can cause reversible irritation; aryl esters may hydrolyze to phenols/acids which are also irritants.
PPE: lab coat, safety glasses, appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid dust inhalation.
Engineering controls: use in a certified chemical fume hood with local exhaust ventilation; avoid aerosol generation.
Incompatibilities: strong bases and nucleophiles (ester saponification); strong acids under heating (ester hydrolysis); strong oxidizers; reducing agents (can reduce the ketone and/or nitrile). Avoid moisture for long-term stability to minimize slow ester hydrolysis.
First aid (overview; defer to SDS):
Eyes: rinse cautiously with water for several minutes; remove contacts; seek medical attention if irritation persists.
Skin: wash with soap and water; remove contaminated clothing.
Inhalation: move to fresh air; seek medical advice if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: treat as combustible organic solid; suitable extinguishing media include CO2, dry chemical, or foam. Thermal decomposition may produce CO/CO2 and irritant fumes.
Always consult the product SDS for definitive hazard and response information.
Solvent Selection
This compound is a moderately nonpolar aromatic with polar functional groups (ketone, ester, nitrile), giving good solubility in many aprotic organic solvents.
Polarity class (qualitative, literature): moderately polar, aprotic; poor hydrogen-bond donation; good hydrogen-bond acceptance via carbonyls and nitrile.
For reactions sensitive to hydrolysis (to preserve the acetoxy group), use dry, aprotic solvents: DCM, THF, EtOAc, toluene, or MeCN under anhydrous conditions.
For polar transformations (e.g., nitrile hydrolysis/reduction), DMSO/DMF/MeCN provide high solubility and thermal stability.
For chromatographic purification, normal-phase silica with hexanes/EtOAc or DCM/MeOH gradients typically separates this scaffold from less polar impurities; avoid basic modifiers unless ester hydrolysis is acceptable.
Quick comparison (literature/typical):
DCM vs EtOAc: DCM offers faster kinetics and better solubility for many aromatic ketones; EtOAc is greener and compatible with base-sensitive substrates when dry.
MeCN vs THF: MeCN provides higher polarity and better support for SN1/SN2 ionic processes; THF is versatile for organometallic steps but requires peroxide monitoring (on solvent, not this solute).
Always verify solvent compatibility with your specific reaction conditions and review moisture sensitivity for base/acid-mediated steps.
Storage and Reconstitution
Storage conditions: Room temperature (as provided in Product Data). Store tightly closed in a dry, well-ventilated place away from direct light. Given the presence of an aryl ester, minimizing humidity will help limit slow hydrolysis over long-term storage.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and handling (general guidance for small organic solids):
Solubility: Expected to dissolve readily in dichloromethane, chloroform, ethyl acetate, acetone, acetonitrile, THF, and polar aprotic media (DMF, DMSO) (literature/typical). Poorly soluble in water.
Preparing stock solutions: For synthetic applications, prepare concentrated solutions (0.1–1.0 M) in dry, oxygen-stable solvents (e.g., DCM, THF, MeCN). For analytical or bioassay stocks, 10–100 mM in dry DMSO or MeCN are common; store aliquots to avoid repeated freeze–thaw/exposure.
Stability: Avoid prolonged exposure to strong acids/bases and moisture. Limit heating to prevent ester cleavage; if drying is needed, use high vacuum at ambient to 40 °C.
Packaging: Keep in amber or opaque containers to reduce unintended photochemistry associated with benzophenone chromophores.
Disposal: Dispose of waste and contaminated materials as halogen-free organic waste unless process introduces halogens/metals; follow institutional and local regulations.
For lot-specific stability and any special handling instructions, refer to the CoA and SDS.
Research use note: For research use only (as stated in Product Data).
Structure and Identity
A benzophenone derivative bearing an ortho acetoxy substituent on one ring and a meta nitrile on the other, useful as a bifunctional aromatic building block.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: C16H11NO3 (computed/literature for this structure)
Molecular weight: ~265.27 g/mol (computed from formula; literature)
Structural features (descriptive):
Core scaffold: benzophenone (diphenyl ketone) with a central carbonyl linking two phenyl rings.
Ring A: substituted at the 2-position by an acetoxy group (–O–C(=O)CH3), indicating a protected salicylate-like phenol (ortho to the ketone). The acetoxy is an aryl ester (phenyl acetate motif).
Ring B: substituted at the 3′-position by a nitrile (–C≡N), a strong electron-withdrawing, meta-directing group.
Functional groups: aromatic ketone, aryl ester, and aryl nitrile. No stereocenters; overall molecule is achiral.
2D description: two conjugated phenyl rings flanking a carbonyl; one ring bears an ortho acetoxy substituent adjacent to the carbonyl; the opposing ring bears a meta nitrile relative to the carbonyl-bearing ipso.
Identity notes:
The combination of ketone, nitrile, and masked phenol (acetate) provides orthogonal handles for selective transformations in synthetic sequences.
For definitive structure confirmation and lot-specific identity (NMR/HRMS/IR), consult the Certificate of Analysis (CoA).
Synthetic Utility
Key functional handles and their reactivity enable convergent and divergent synthesis:
Aryl ester (2-acetoxy):
Protects an ortho-phenol; removable under mild basic (K2CO3/MeOH, NaHCO3/MeOH–H2O) or acidic conditions (AcOH, catalytic H2SO4) to unveil 2-hydroxybenzophenone.
Can participate in transesterification (NaOMe/MeOH) or be converted to the corresponding phenoxide for SNAr if an activated aryl electrophile is present.
Benzophenone carbonyl:
Reductions (NaBH4, catalytic hydrogenation) yield benzhydrols; Wolff–Kishner or Clemmensen conditions can deoxygenate to diarylmethanes when compatible with other groups (literature caution for ester/nitrile stability).
Formation of imines/oximes followed by Beckmann rearrangement or reductive amination to introduce amine functionality.
Nitrile (meta on ring B):
Hydrolysis to amide/acid (acidic or basic conditions; stepwise). Partial reduction to amine (LiAlH4, BH3, or catalytic H2/Ni) affords anilines after subsequent transformations.
Useful as a directing group for ortho-lithiation, enabling further substitution patterns before nitrile functional-group interconversion.
Retrosynthetic value:
The scaffold can arise from acylation of a cyanobenzene derivative with a salicylic acid derivative (followed by O-acetylation), or from Friedel–Crafts benzoylation strategies using protected salicyl phenyl precursors.
Selectivity notes:
Sequence transformations to preserve sensitive groups: conduct carbonyl and nitrile manipulations under conditions that avoid ester saponification unless deprotection is intended.
Chelation effects from the salicylophenone (post-deacetylation) can control ortho/para selectivity and facilitate intramolecular reactions (e.g., formation of benzoxazinones via cyclizations).
Target Specificity
Not applicable. This product is a small-molecule chemical intermediate and is not an antibody, enzyme, or biological probe with defined target specificity.
Antigen/epitope, clone, isotype, or species reactivity: Not applicable.
For biochemical targeting studies, any binding or activity would need to be established experimentally for your system.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
