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Application Protocols
Item-specific, validated protocols and dilutions: Not specified for this item; refer to any method notes provided with your order.
General guidance (research use):
GC–MS/LC–MS internal standard: Spike at a known concentration close to the expected analyte level (e.g., 0.1–10 µg/mL depending on method). Prepare stock in acetonitrile or methanol; verify stability and no co-elution with matrix peaks. Monitor a diagnostic M+2 transition or ¹³C-specific fragments.
NMR experiments: For ¹³C NMR, concentrations of 50–200 mM in CDCl3, DMSO-d6, or acetone-d6 provide strong signals. For ¹³C–¹³C coupling observations, consider INADEQUATE or 2D ¹³C–¹³C correlation with long acquisition times and suitable relaxation delays.
Biocatalysis assays: Dissolve in minimal DMSO/MeOH, dilute into buffered enzyme media (<1–2% organic cosolvent v/v). Track conversion by LC–MS, using the isotope pattern to confirm product carbon origin.
Document the exact isotopic enrichment and positions from the CoA to ensure correct quantitation and data interpretation.
Biological Roles
Item-specific biological data: Not specified for this item.
General context (research use only; literature):
Acetophenone is not a native metabolite in humans but can appear as a minor component in flavor/fragrance matrices and as a biotransformation product in certain microbial pathways.
¹³C-labeled acetophenone can serve as a tracer in biocatalysis studies, e.g., to follow ketone reductions by alcohol dehydrogenases or Baeyer–Villiger monooxygenases, enabling assignment of carbon incorporation and fate in products.
In stable-isotope probing (SIP) experiments, ¹³C labeling facilitates the tracking of substrate assimilation into biomass or products, when compatible organisms/enzymes accept acetophenone or its derivatives.
NMR-based metabolomics or enzyme mechanism elucidation: dual-¹³C labels in the acetyl fragment allow detection of ¹³C–¹³C couplings in intermediates or reduced alcohols (1-phenylethanol), aiding pathway mapping.
Note: No clinical/therapeutic uses are implied. For all biological experiments, ensure that solvent vehicles and concentrations are non-denaturing/non-toxic to the biocatalyst used and that isotopic enrichment and position are appropriately documented for data interpretation.
Buffer Applications
Not typically applicable. Acetophenone-α,β-¹³C₂ is a hydrophobic organic ketone and is not used as a buffering agent. For aqueous work, it may be dissolved in miscible co-solvents (e.g., DMSO, MeOH) and then added to buffered systems as a substrate or analytical standard. Refer instead to Reaction & Applications and Synthetic Utility for relevant usage guidance.
Green Alternatives
Context: This product is a labeled building block/standard rather than a solvent or bulk reagent. Greener considerations focus on reaction media and transformations used with it, not replacement of the compound itself.
Greener choices (literature guidance):
Solvent selection: prefer 2-MeTHF, CPME, EtOAc, MeOH/EtOH, or water-organic biphasic systems over chlorinated solvents when compatible with reactivity.
Oxidation/reduction: choose catalytic, atom-economical methods (e.g., transfer hydrogenation, catalytic aerobic oxidations with TEMPO/metal catalysts) over stoichiometric chromium or borane reagents.
Aldol/condensation: employ solid-supported bases or organocatalysts in green solvents; consider aqueous micellar conditions if feasible.
Illustrative comparison (general):
DCM vs EtOAc: EtOAc offers lower toxicity and better environmental profile, often adequate for extractions and chromatography of acetophenone derivatives.
THF vs 2-MeTHF/CPME: 2-MeTHF and CPME have improved safety (peroxide resistance, higher boiling points), renewable sourcing (2-MeTHF), and favorable LCA metrics, while supporting similar enolate chemistry.
Waste minimization:
Use microscale/flow methods for mechanistic isotopic studies to reduce labeled material consumption.
Recycle solvents through distillation or employ solvent-less (neat) conditions for photochemical steps when safe and practical.
Pharmaceutical Uses
Item-specific pharmacopeial status/excipient role: Not specified for this item; refer to CoA/Spec Sheet.
General, non-clinical context (research/manufacturing only):
Stable-isotope–labeled standards are widely used in analytical method validation and QC by LC–MS/GC–MS to ensure accurate quantitation of related substances or residual solvents in drug substances and intermediates. A ¹³C₂-acetophenone internal standard can improve precision for assays involving acetophenone or its transformation products.
Process studies: labeled substrates help deconvolute reaction pathways in route scouting (e.g., tracing carbon migration in Baeyer–Villiger or reduction sequences) to optimize impurity control.
No therapeutic or clinical claims are made or implied. Any use in regulated environments should verify compendial requirements, isotopic enrichment documentation, and impurity limits on a lot-specific CoA.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values for acetophenone (apply closely to ¹³C-labeled analogs; isotopic substitution minimally affects bulk properties):
Appearance: colorless to pale-yellow liquid at room temperature (literature)
Melting point: ~19–20 °C (literature)
Boiling point: ~202–204 °C at 1 atm (literature)
Density: ~1.028 g/mL at 25 °C (literature)
Refractive index (n20 D): ~1.532 (literature)
Water solubility: ~5–7 g/L at 20–25 °C; miscible with many organic solvents (EtOH, Et2O, DCM, toluene) (literature)
LogP (octanol/water): ~1.6–1.7 (literature)
Vapor pressure: low at ambient temperature; on the order of ~0.3–0.5 mmHg at 25 °C (literature)
UV absorption: strong π→π* bands in the UV (benzoyl chromophore); often used as a UV reference around 240–280 nm (literature)
Molecular weight (monoisotopic/computed): unlabeled acetophenone 120.15 g/mol; ¹³C₂ isotopologue increases by ~+2.00 Da to ~122.16 g/mol (computed, literature). Exact mass depends on isotopic enrichment pattern.
Important: The above values are for general reference only and are not the item’s guaranteed specifications. Always consult the product’s CoA/SDS for authoritative data.
Quality and Grades
Item-specific grade/purity, stabilizers, and analytical limits: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting typical grades (general information):
Isotopic enrichment: For ¹³C-labeled reagents, two separate metrics matter: chemical purity (organic assay, GC/HPLC) and isotopic enrichment at each labeled position (e.g., ≥98 atom % ¹³C). These are distinct and both influence data quality in NMR/MS tracer studies.
Residual solvents and water: Low residuals are important for quantitative NMR or kinetic isotope effect work. Karl Fischer or GC headspace data are commonly provided on CoA.
UV/LCMS suitability: For LC/UV applications, low baseline absorbance impurities are preferred. For MS, low metal/ionic content minimizes adduct formation.
Stabilizers: Aromatic ketones typically do not require added stabilizers; if any are present, they should be disclosed on the CoA as they may interfere in photochemical or radical processes.
Best practice:
Verify both chemical purity and isotopic enrichment specifications on the CoA before use in quantitative studies.
For mechanistic studies, document the exact enrichment pattern at the α and β positions to enable correct isotopologue accounting.
Reaction and Applications
Focus: dual-¹³C-labeled acetophenone is a tracer/standard for mechanistic, metabolic, and analytical studies. All uses are for research only.
Representative applications (literature/general):
Isotopic tracing by NMR: ¹³C–¹³C coupling across the acetyl fragment provides enhanced structural information; 1D/2D ¹³C NMR (e.g., INADEQUATE) can track carbon flow in condensations, oxidations, and rearrangements.
Mass spectrometry internal standard: +2 Da mass shift relative to unlabeled acetophenone improves quantitation in GC–MS/LC–MS assays, including monitoring of derivatized products.
Kinetic isotope effect controls: Although ¹³C KIEs are small, dual labeling can improve precision in competitive experiments.
Model substrate in named reactions: participates in Claisen–Schmidt condensations, Baeyer–Villiger oxidation (to phenyl acetate), Wolff–Kishner/Clemmensen reductions (to ethylbenzene), and α-alkylation/acylation via enolates—all enabling carbon tracing of product distribution.
Photochemistry and radical reactions: benzylic hydrogen abstraction and α-cleavage (Norrish I) can be probed with ¹³C tracking of fragment origins.
Practical tips:
Maintain anhydrous conditions for base-mediated enolate chemistry to prevent isotope scrambling via exchange.
Record the exact isotopic pattern and enrichment for data analysis; set up MS methods to resolve M+2 from natural abundance envelopes.
For NMR, enrich acquisition settings (inverse-gated ¹³C, DEPTQ) to avoid NOE biases in quantitation.
Reaction Conditions
General literature guidance (not item specifications):
Enolate formation/α-alkylation: LDA (1.1–1.5 equiv) in dry THF or THF/hexanes at −78 to −40 °C; then add electrophile (alkyl halide, carbonyl) and warm to 0–25 °C. Typical times 0.5–2 h for deprotonation; 1–4 h for trapping. Quench with NH4Cl. Aim to minimize proton exchange that could dilute ¹³C labeling.
Reduction to 1-phenylethanol: NaBH4 (1.1–1.5 equiv) in MeOH or EtOH at 0–25 °C, 0.5–2 h; or catalytic hydrogenation (Pd/C, H2, 1–3 bar) in EtOH/EtOAc at RT. Isotope pattern retained at carbonyl/methylene carbon in the product.
Baeyer–Villiger oxidation: mCPBA (1.2–1.5 equiv) in DCM at 0–25 °C, 2–6 h to give phenyl acetate; catalytic variants (e.g., peracids formed in situ, or enzymatic BVMO) are available. Track migration and carbonyl insertion via ¹³C.
Claisen–Schmidt (to chalcone): base (NaOH, KOH, or amines) in EtOH or aqueous EtOH at 0–25 °C, 1–12 h with substituted benzaldehydes; control self-condensation by stoichiometry/temperature.
Photochemistry (Norrish I α-cleavage): UV irradiation (e.g., 254–300 nm) in UV-transparent solvents (MeCN); monitor by GC–MS to observe ¹³C-labeled fragments.
Notes:
Use rigorously anhydrous conditions for base-mediated steps to avoid isotope scrambling.
For MS quantitation, calibrate to distinguish M, M+1 (natural ¹³C), and M+2 (label) envelopes.
Safety and Handling
Item-specific GHS data: Not specified; refer to SDS for this lot/item.
General safety information for acetophenone and ¹³C-labeled analogs (literature; not specific to this item):
Hazard nature: combustible liquid; irritant to eyes/skin; harmful if swallowed or inhaled at sufficient doses. Avoid aerosol generation.
PPE: use lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Employ local exhaust ventilation or fume hood.
Incompatibilities: strong oxidizers (risk of exotherm), strong bases/acids under conditions promoting aldol/condensation or hydrolysis. Avoid peroxides/strong reducing agents.
Handling: minimize skin contact and inhalation. Keep containers tightly closed. Use in well-ventilated areas or fume hood. Prevent contamination with strong bases if enolate formation is undesired.
First aid (overview):
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; remove contacts if present and easy; seek medical advice if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire fighting: use dry chemical, CO2, or alcohol-resistant foam. Cool containers with water spray.
Always defer to the product-specific SDS for definitive hazard statements, pictograms, exposure limits, and emergency procedures.
Solvent Selection
Relevance: This product is itself an organic liquid (aromatic ketone), not a solvent by design. However, understanding its solvent compatibility assists in reaction planning and analytical work.
General solvent compatibility and polarity (literature):
Polarity/class: moderately polar, aprotic aromatic ketone; engages in dipole–dipole interactions and π–π stacking.
Miscibility: miscible with common organic solvents (MeOH/EtOH, acetone, DCM, chloroform, diethyl ether, THF, toluene, hexanes to a lesser extent). Low-to-moderate solubility in water (~5–7 g/L at 20–25 °C).
Dielectric considerations: dissolves well in media with ε ~7–40 (e.g., toluene to acetonitrile). Polar aprotic solvents enhance reactions proceeding via its enol/enolate.
When to choose particular media:
Enolate chemistry/alkylation: dry THF, DME, or toluene with strong, non-nucleophilic bases (LDA, KHMDS) favor clean deprotonation at the benzylic (α) site.
Oxidations/reductions: DCM or MeCN for electrophilic oxidants; alcohols or ethereal solvents for hydride reductions.
Photochemical work: use non-aromatic, UV-transparent solvents (e.g., acetonitrile) to minimize background absorption from solvent.
Small comparison (literature):
In MeCN: higher polarity, good for MS coupling and fast kinetics; in toluene: better for Friedel–Crafts or radical reactions; in THF: excellent for low-temperature enolate generation and subsequent trapping.
Storage and Reconstitution
Item-specific storage: Room temperature (per Product Data). Shipped-in conditions: Not specified for this item; refer to CoA/Spec Sheet.
General guidance:
Storage: Keep tightly closed in an inert atmosphere (e.g., nitrogen) if possible, away from light and sources of ignition. Store in a dry place to limit hydrolysis/side reactions in base-catalyzed environments.
Stability: Aromatic ketones are generally stable at ambient conditions; avoid prolonged exposure to strong light/UV if photoreactivity is a concern for your application.
Reconstitution/Preparation: Typically supplied neat. For solution preparation, use dry, high-purity solvents (e.g., CDCl3 for NMR; MeCN/MeOH for MS). Record solvent lot and water content if using for quantitative work.
Freeze–thaw: Not applicable to neat liquids; if stored as solutions, minimize freeze–thaw cycles and use amber vials where photostability matters.
Always consult the item’s CoA/SDS for any lot-specific handling, storage, and stability instructions. Research use only.
Structure and Identity
Item-specific (from Product Data):
SKU: A473856
Product name: Acetophenone-α,β-¹³C₂
CAS: 190314-15-9
PubChem CID: 16213368
InChIKey: 191580 (as provided)
Storage conditions: Room temperature
Category: 全部 / 可售 / 化学和生化试剂
Literature/computed (general identity for the ¹³C₂-isotopologue of acetophenone; not item specifications):
Core scaffold: an aromatic ring (phenyl) bonded to a methyl ketone (acetyl) group (i.e., a phenyl methyl ketone).
Functional groups: aryl ring, ketone (C=O), benzylic methyl group capable of enolization.
Isotopic labeling: two carbons in the acetyl fragment are ¹³C-enriched. ¹³C labeling does not alter connectivity but enables NMR/MS tracing. A canonical isotopically annotated SMILES often used is [13CH3]13Cc1ccccc1 (literature depiction; not item spec).
2D description: a benzene ring (six sp2 carbons) para to no substituents, bearing at one ring carbon a carbonyl carbon double-bonded to oxygen and single-bonded to a methyl carbon; the two carbons of the acetyl unit carry ¹³C isotopic enrichment in this isotopologue.
Notes:
Molecular formula (connectivity) corresponds to the acetophenone framework C8H8O; isotopic composition is ¹³C2-enriched (literature).
Synthetic Utility
Chemical features enabling reactivity (literature):
Benzylic α-CH acidity (pKa of conjugate acid ~–7; effective α-C–H pKa in DMSO ~24) allows clean enolate formation with strong base, enabling α-alkylation, acylation, and Michael additions.
Carbonyl group undergoes standard ketone transformations: reductions (to 1-phenylethanol), oxidations (to benzoic acid derivatives via Baeyer–Villiger then hydrolysis), and condensations (Claisen–Schmidt to chalcones).
Aromatic ring supports electrophilic substitution on deactivated ring positions under strong conditions; metalation (e.g., ortho-lithiation with directing groups) possible in derivatives.
Use of the ¹³C₂ label:
Traces the fate of the acetyl carbons in C–C bond-forming reactions (aldol, Claisen–Schmidt), rearrangements (Baeyer–Villiger), and reductions/oxidations.
Facilitates ¹³C–¹³C correlation experiments to confirm connectivity after transformations.
Retrosynthetic/value:
As a benzylic ketone, acetophenone serves as a strategic handle to access a wide manifold of aryl-ethyl skeletons. The isotopic label preserves through many transformations, enabling isotope-resolved impurity profiling and mechanism mapping.
Target Specificity
Not applicable. This product is a small-molecule isotopically labeled ketone, not a biological targeting reagent (e.g., antibody, inhibitor with defined target spectrum). No antigen, epitope, or species reactivity is associated with this item.
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.
