4-Cyano-3'-methoxybenzophenone - ≥95% , CAS No.750633-60-4

CAS: 750633-60-4 Cat. No.: C974669 Formula: C₁₅H₁₁NO₂ Peso molecolare: 237.258 PubChem CID: 24722777

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: COC1=CC=CC(=C1)C(=O)C2=CC=C(C=C2)C#N
• IUPAC Name: 4-(3-methoxybenzoyl)benzonitrile
• InChIKey: TZKPZLKZSQMCJL-UHFFFAOYSA-N
• INCHI: 1S/C15H11NO2/c1-18-14-4-2-3-13(9-14)15(17)12-7-5-11(10-16)6-8-12/h2-9H,1H3
• Isomeri SMILES: COC1=CC=CC(=C1)C(=O)C2=CC=C(C=C2)C#N
• PubChem CID: 24722777
• Peso molecolare: 237.258

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzophenones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzophenones
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzophenones
• Alternative Parents: Diphenylmethanes Aryl-phenylketones Phenoxy compounds Methoxybenzenes Benzoyl derivatives Benzonitriles Anisoles Alkyl aryl ethers Nitriles Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzophenone - Aryl-phenylketone - Diphenylmethane - Phenoxy compound - Anisole - Benzonitrile - Benzoyl - Methoxybenzene - Aryl ketone - Phenol ether - Alkyl aryl ether - Ketone - Ether - Nitrile - Carbonitrile - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Cyanide - Organic oxygen compound - Aromatic homomonocyclic compound
• Descrizione: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 237.250 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 237.079 Da
• Monoisotopic Mass: 237.079 Da
• Topological Polar Surface Area: 50.100 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 336.000
• 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

Application Protocols

No manufacturer-validated application protocols are provided for this item.

• General laboratory usage suggestions (non-binding)

  • Synthetic reactions: Weigh compound accurately, dissolve in a suitable dry organic solvent, and proceed under inert atmosphere if using moisture-sensitive reagents.
  • Analytical characterization: Typical methods include 1H/13C NMR (aromatic and carbonyl resonances; nitrile carbon near ~115–120 ppm, literature), IR (C=O ~1650–1680 cm−1; C≡N ~2220–2260 cm−1; Ar–O–CH3 ~1240–1270 cm−1), MS (M+ at m/z ~237, literature), and HPLC/UV.
  • Purification: Silica gel chromatography using hexanes/EtOAc gradients; confirm identity and purity by orthogonal methods.

• For any specific protocols (e.g., exact solvent volumes, temperatures, or analytical system suitability), please refer to your internal methods or develop/qualify methods as needed.

Biological Roles

This product is a synthetic aromatic small molecule intended for laboratory research and chemical synthesis.

• General information (not medical/clinical; literature context)

  • No established biological role in metabolism or signaling. It is not a natural metabolite.
  • The benzophenone chromophore can act as a photo-crosslinking handle in biochemical probe design; cyano and methoxy substituents provide tunability of photophysical properties. Such uses require derivatization and validation.
  • Aromatic nitriles and benzophenones may interact with biomolecules under UV irradiation (e.g., photoaffinity labeling), but specificity and safety must be experimentally determined.

• Not applicable elements

  • There are no known endogenous targets or pathways specific to 4-cyano-3'-methoxybenzophenone.
  • No claims are made regarding therapeutic, diagnostic, or clinical applications.

• Research-only statement

  • For research use only. Not for human or veterinary use.

Buffer Applications

This is not a buffering reagent and is not typically used to prepare aqueous buffer systems.

• Practical guidance
  • If handling in biological assays, dissolve in an appropriate organic co-solvent (e.g., DMSO or acetonitrile) before diluting into assay media, ensuring final organic content is compatible with the system.
  • No buffering capacity, pKa, or ionic speciation data are provided for this item; refer to CoA/Spec Sheet for any solubility notes relevant to your application.

Green Alternatives

Greener choices pertain mainly to solvent and reagent selection for transformations of this substrate.

• Solvent alternatives (general guidance)

  • Replace chlorinated solvents (DCM/CHCl3) with ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME), or propylene carbonate when feasible.
  • Favor ethanol or isopropanol for reductions/hydrogenations instead of isopropyl ether or toluene when compatible.

• Reagent choices (general)

  • Carbonyl reductions: Use catalytic hydrogenation (H2/Pd) or transfer hydrogenation (e.g., Ru/Mn catalysts with iPrOH) instead of stoichiometric hydrides.
  • Nitrile hydrolysis: Employ aqueous conditions and catalytic acids/bases; avoid high-boiling polar aprotics if not required.
  • O-Demethylation: Explore catalytic demethylation (e.g., aluminum- or iron-based catalysts) or oxidative demethylation where selectivity allows, as alternatives to BBr3.

• Comparison snapshot (general)

  • DCM vs 2-MeTHF: 2-MeTHF is biomass-derived, lower toxicity, and supports organometallics; DCM offers unmatched volatility for easy removal but is chlorinated and problematic for EHS.
  • DMF/DMAc vs Acetonitrile/EtOAc: MeCN/EtOAc are easier to remove, have better EHS profiles, and can often substitute for medium-polarity needs.

• Process notes

  • Solvent recycling and reduced solvent volumes often provide the largest green impact.
  • Choose room-temperature or flow photochemistry for benzophenone-mediated steps to minimize energy input.

• Item-specific green data: Not specified for this item; refer to CoA/Spec Sheet if available.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item.

• General, non-clinical context

  • Substituted benzophenones are sometimes used as intermediates in the synthesis of drug candidates and performance materials. The cyano and methoxy groups enable diversification to amides, acids, amines, and phenols.
  • The UV-active benzophenone core can be useful in process analytics (e.g., HPLC/UV monitoring) for intermediate tracking.

• Not specified for this item; refer to CoA/Spec Sheet

  • Compliance with USP/Ph. Eur. monographs (if any), residual solvent limits, bioburden/endotoxin, and other GMP-related parameters are not specified here.

• Compliance note

  • Supplied for research use only. Not for use in human or veterinary formulations.

Physical Properties

• Item-specific specs

  • 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 and expectations (for context; not item specifications)

  • Phase: Typically a crystalline aromatic solid for substituted benzophenones (literature/general trend)
  • Molecular weight (from literature formula C15H11NO2): ~237.26 g/mol
  • Polarity: Moderately polar aromatic due to carbonyl and nitrile; overall hydrophobic with limited aqueous solubility (general)
  • Solubility profile (general): Good solubility expected in chlorinated solvents (CH2Cl2, CHCl3), ethyl acetate, acetone, acetonitrile, THF, and aromatic solvents (toluene); poor in water.
  • UV–Vis: Benzophenone chromophore absorbs in near-UV; substituents shift maxima (literature/general; specific λmax not provided here)

• Not specified for this item; refer to CoA/Spec Sheet

  • Melting point, boiling point, density, refractive index, logP/logD, pKa, vapor pressure.

Quality and Grades

• Item-specific status

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades (general guidance)

  • Research/Technical grade: Suitable for most synthetic applications; impurities may include residual solvents or closely related organics.
  • High-purity/AR grade: Tighter limits on assay and common metal/halide residues; suitable for analytical and sensitive synthetic work.
  • HPLC grade (if applicable to solvents/UV-sensitive uses): Low non-volatile residue and low UV absorbance; relevant if using as a standard or chromophore reference.

• Practical quality considerations for this compound class (general)

  • UV purity: Benzophenone chromophores are UV-active; trace colored/UV-absorbing impurities can interfere with photochemical or analytical work.
  • Moisture: While aryl ketones/nitriles are not highly hygroscopic, surface moisture can affect weight accuracy and some base- or acid-catalyzed reactions. Dry over P2O5 or in vacuo if needed (general practice).
  • Trace metals/halides: If using in cross-coupling or photoredox studies, low metal content can be important; consult CoA if relevant.

• Documentation

  • For definitive specifications (assay, residual solvents, metal content, UV cutoff), please consult the product’s CoA/Spec Sheet.

Reaction and Applications

As a functionalized benzophenone, 4-cyano-3'-methoxybenzophenone is a versatile intermediate for constructing complex aromatics and heterocycles.

• Carbonyl chemistry (general literature)

  • Nucleophilic additions: Grignard/organolithium reagents add to the aryl ketone to give tertiary carbinols (benzhydrol derivatives). Use rigorously dry ether/THF at −78 to 0 °C.
  • Reductions: NaBH4 (mild) or catalytic hydrogenation reduces the carbonyl to a secondary alcohol; stronger reagents (LiAlH4) also tolerated but may affect the nitrile under forcing conditions.
  • Oxime/hydrazone formation: Condensation with hydroxylamine or hydrazines enables subsequent transformations (e.g., Beckmann-related chemistry, Wolff–Kishner on hydrazones).

• Nitrile handle transformations (general literature)

  • Hydrolysis: To amide (acidic or basic, controlled) or to carboxylic acid under stronger conditions.
  • Reduction: To primary amine (e.g., Raney Ni/H2, Pd/C/H2, or borane); to aldehyde via DIBAL-H at low temperature.
  • Cycloadditions: [3+2] with azide to tetrazoles under Lewis acid/thermal conditions.

• Methoxy substituent leverage (general literature)

  • O-Demethylation: BBr3 or HBr/AcOH provides the phenol, enabling further coupling or etherification.
  • Directing effects: The methoxy can activate the ring toward electrophilic substitution and direct ortho/para in subsequent functionalizations (relative to the methoxy-bearing ring).

• Photochemistry (general note)

  • Benzophenone cores populate long-lived triplet states under UV, enabling hydrogen abstraction and photoinitiation applications; substituents (cyano/methoxy) tune absorption and reactivity.

• Typical uses

  • Advanced intermediate for polyaryl architectures, photoactive materials, and scaffold diversification in discovery chemistry. No manufacturer-specific application text was provided; the above expands general synthetic utility.

Reaction Conditions

General literature conditions for transforming this scaffold (guidance only; optimize per lab data):

• Carbonyl reductions

  • NaBH4 in MeOH/EtOH or THF at 0–25 °C, 1–4 h, typically good to excellent yields to secondary alcohols. Avoid conditions that also reduce the nitrile if selectivity is required.
  • Catalytic hydrogenation (Pd/C, H2 1–5 bar) in EtOH or EtOAc at RT–50 °C can reduce the ketone; higher pressure/longer time may also reduce –CN.

• Nucleophilic additions (Grignard/organolithium)

  • RMgX or RLi in dry THF/Et2O at −78 to 0 °C, 1–3 equiv, giving tertiary alcohols. Quench with NH4Cl; protect nitrile if necessary to avoid over-addition in more reactive systems.

• Nitrile transformations

  • Hydrolysis to amide: Aqueous acid (H2SO4 or HCl) or base (NaOH) at reflux (MeOH/H2O or dioxane/H2O), 6–24 h.
  • Hydrolysis to acid: Stronger/longer conditions (e.g., 6 M HCl or 6 M NaOH, reflux), 12–48 h.
  • Reduction to amine: H2, Pd/C or Raney Ni (3–10 bar) in EtOH/MeOH at 25–60 °C; or BH3·THF, 0–25 °C.
  • Partial reduction to aldehyde: DIBAL-H (1.1–1.5 equiv) in toluene/CH2Cl2 at −78 to −20 °C.

• O-Demethylation

  • BBr3 (1–3 equiv) in DCM at −78 to 0 °C, 1–6 h, then aqueous workup to give the phenol. Alternative: HBr/AcOH reflux.

• Electrophilic aromatic substitution on anisole ring

  • Nitration, halogenation, or formylation under controlled conditions, leveraging o/p-directing methoxy (avoid overreaction; protect carbonyl if needed).

• Notes

  • Typical yields and times vary with scale and substitution; monitor by TLC/HPLC. These are literature-style conditions and not item-specific specifications.

Safety and Handling

• Item-specific hazard information

  • 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 considerations for aryl ketones and aryl nitriles (literature/general guidance; defer to SDS)

  • Hazards: May cause eye/skin/respiratory irritation. Aryl nitriles are generally of low volatility but should be handled to minimize exposure. Avoid dust formation and inhalation of particulates.
  • PPE: Lab coat, safety glasses or goggles, appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to control vapors/particulates.
  • Incompatibilities: Strong oxidizers (risk of exotherm), strong bases/acids may effect hydrolysis or demethylation under forcing conditions; reducing agents can reduce the carbonyl or nitrile.
  • Fire safety: Likely combustible organic solid. Keep away from ignition sources; use CO2, dry chemical, or foam for extinguishing.
  • First aid (overview; consult SDS):
    • 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 advice if irritation persists.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Environmental: Prevent release to the environment; collect spills with inert absorbent and dispose according to regulations.

• Special notes

  • This compound is not an ether solvent; peroxide formation is not a typical concern.
  • Always consult the current SDS for authoritative safety, toxicological, and regulatory information.

Solvent Selection

This aromatic ketone with nitrile and methoxy substituents is moderately polar but largely hydrophobic.

• Polarity/miscibility profile (general)

  • Expected to dissolve well in: dichloromethane, chloroform, THF, acetone, ethyl acetate, acetonitrile, DMF/DMSO, and aromatic solvents (toluene, xylene).
  • Poorly soluble in: water and very nonpolar aliphatic hydrocarbons at ambient temperature (general trend for substituted benzophenones).

• Use-case-driven selection (general guidance)

  • Reaction medium for nucleophilic additions to the carbonyl: THF, toluene, or etheric solvents for Grignard/organolithium additions; DCM/EtOAc for NaBH4 reductions when compatible.
  • Nitrile transformations (hydrolysis/reduction): Aqueous alcoholic mixtures (EtOH/H2O) under acid/base catalysis for hydrolysis; protic solvents or THF/EtOH for catalytic hydrogenation of nitriles.
  • O-Demethylation: Non-nucleophilic chlorinated solvents (DCM) or toluene often used with BBr3 or AlCl3 (general literature practice).

• Quick comparison (general)

  • DCM vs THF: DCM offers good solubility and easy workup; THF supports organometallic chemistry and broader temperature window.
  • Acetonitrile vs DMF: MeCN provides polarity with easier removal; DMF offers higher polarity/boiling point for challenging transformations.

• Note: Optimize solvent choice against base/acid sensitivity of the substrate and the intended transformation. No item-specific solvent specs are provided for this product.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (as provided in Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance for aromatic ketones/nitriles

  • Keep tightly closed in a dry, well-ventilated place. Store in original container or in amber glass to minimize light exposure (benzophenones are UV-active).
  • Protect from prolonged light and heat; store desiccated if precise weighing is critical.
  • Segregate from strong oxidizers and strong acids/bases if long-term storage is anticipated.

• Reconstitution/handling

  • Solid handling: If supplied as a solid, dissolve in a compatible organic solvent (e.g., DCM, THF, EtOAc, MeCN, or DMSO) to prepare stock solutions. Filter if necessary to remove particulates.
  • Solution stability: Prepare fresh solutions for sensitive reactions; for longer storage, keep solutions in amber vials under inert gas at low temperature where compatible (general practice). No item-specific solution stability data are provided.

• Shelf-life and specifications

  • Not specified for this item; refer to CoA/Spec Sheet for any retest date or stability information.

Structure and Identity

Brief overview: 4-Cyano-3'-methoxybenzophenone is an aromatic diaryl ketone bearing a para-cyano substituent on one ring and a meta-methoxy substituent on the other. It is a functionalized benzophenone useful as a building block in synthesis.

• Item-specific (from Product Data)

  • SKU: C974669
  • Product Name: 4-Cyano-3'-methoxybenzophenone
  • CAS: 750633-60-4
  • PubChem CID: 24722777
  • InChIKey: 354021 (as provided)
  • Storage: Room temperature
  • Research Use: For research use only

• Literature/computed identifiers and composition (not item specifications)

  • Molecular formula (literature, inferred from structure): C15H11NO2
  • Molecular weight (literature, calculated): ~237.26 g/mol
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general description)

  • Core: Benzophenone scaffold (diphenyl ketone, Ar–CO–Ar)
  • Ring A: para-cyano (–C≡N) substituent relative to the carbonyl carbon
  • Ring B: meta-methoxy (–OCH3) substituent relative to the carbonyl carbon
  • Functional groups: Aryl ketone (conjugated), aryl nitrile, aryl ether (methoxy)
  • Conjugation: Extended π-system over two phenyl rings and carbonyl; additional conjugation with the nitrile on one ring
  • Stereochemistry: None (achiral, no stereocenters)
  • 2D structure in words: Two benzene rings linked by a central carbonyl carbon; one ring bears a para-cyano substituent; the other ring bears a meta-methoxy substituent.

Synthetic Utility

Key functional handles and retrosynthetic opportunities make 4-cyano-3'-methoxybenzophenone a valuable intermediate.

• Functional group synthon roles (general literature)

  • Aryl ketone (Ar–CO–Ar): Entry to tertiary benzhydrols via nucleophilic addition; enone formation via Wittig/Julia after carbonyl activation; oxime/hydrazone derivatives as masked forms for further manipulations.
  • Aryl nitrile (–C≡N): Convertible to carboxamide, carboxylic acid, aldehyde, or amine, enabling branch points to diverse functionalities and ring-forming reactions (e.g., tetrazole synthesis).
  • Methoxy aryl ether: Switchable to phenol by demethylation (BBr3, AlCl3, HBr), unlocking O-alkylation, O-acylation, or cross-coupling (via subsequent triflation/halogenation).

• Retrosynthetic disconnections (conceptual)

  • Disassemble at the carbonyl: A benzoyl equivalent plus a substituted aryllithium/Grignard, or acylation (e.g., Friedel–Crafts acylation on an anisole derivative) followed by nitrile introduction.
  • Introduce –CN late-stage: From aryl halide via Pd-catalyzed cyanation (e.g., Zn(CN)2, K4[Fe(CN)6]) on a para-halobenzophenone precursor.

• Scaffold elaboration

  • Electrophilic aromatic substitution favored on the anisole ring (o/p directing) for further functionalization.
  • Directed ortho-metalation adjacent to methoxy under strong base (s-BuLi/TMEDA) for installable handles.

• Purification/handling (general)

  • Typically amenable to silica gel chromatography (hexanes/EtOAc or toluene/EtOAc). Crystallization from EtOAc/hexanes or toluene/MeOH mixtures often works for benzophenone derivatives.

Target Specificity

Not applicable. This product is a small-molecule chemical, not a biological reagent (e.g., antibody, enzyme, or ligand with defined biomolecular targets). No target, epitope, clone, isotype, or species reactivity information is provided for this item.