This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Revisões
Avaliações dos Clientes
Application Protocols
No assay/application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent.
Synthetic protocols: See the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for generalized procedures and conditions relevant to using this compound as a building block.
For lab deployment, consult internal SOPs for reaction setup, purification, and analytical characterization (NMR, LC–MS, HPLC).
Biological Roles
This product is a small synthetic aromatic α-hydroxy ketone and is not a biological buffer, metabolite, or biomacromolecule.
General context (literature)
Phenacyl motifs are widely used as photolabile protecting groups (PPGs) in chemical biology to cage carboxylates, phosphates, and phenols; however, that application typically employs phenacyl bromides or activated phenacyl derivatives rather than the free alcohol. The free alcohol can be converted to such derivatives via esterification or Mitsunobu coupling.
The compound itself does not have a known endogenous biological role or metabolic pathway assignment. Aryl α-hydroxy ketones can undergo phase I/II metabolism (oxidation, conjugation) in vivo, but such data are context-dependent and not specific to this item.
Use limitations
For research use only. Not for diagnostic, therapeutic, or clinical applications.
For any biological testing or probe development, researchers should establish cytotoxicity and stability profiles de novo, as item-specific bioactivity data are not provided here.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biological or analytical buffer systems.
If your workflow involves buffers, consider using this product as a synthetic intermediate upstream, then perform buffer preparation with standard systems (e.g., phosphate, HEPES, Tris) after workup and purification of target molecules.
No buffer recipes or pH ranges apply to this product.
Green Alternatives
Sustainability considerations focus on solvent/reagent choices; the molecule itself is a halogenated aromatic, which may have higher environmental persistence.
Greener solvent swaps (literature-based guidance)
Replace DCM with EtOAc or 2-MeTHF for extractions and many reactions; expect modest rate changes.
Substitute DMF/DMSO where possible with MeCN, 2-MeTHF, CPME, or propylene carbonate depending on reaction class.
Use ethanol or isopropanol as protic solvents instead of MeOH when feasible due to toxicity profile, while balancing reactivity.
Comparison (general)
DCM vs 2-MeTHF: 2-MeTHF is bio-based, less dense, and has lower halogenated waste impact; however, it may require longer reaction times and careful peroxide monitoring.
THF vs 2-MeTHF/CPME: Alternatives offer improved stability and greener sourcing; check miscibility and azeotrope behavior for workups.
Reagent choices
Oxidations: Favor catalytic/O2 systems or TEMPO/bleach over stoichiometric Cr(VI). If using Dess–Martin/IBX, minimize excess and ensure proper waste handling of hypervalent iodine residues.
Couplings: Adopt ligand-efficient palladium catalysis at low loadings or nickel/iron catalysts where compatible; explore aqueous micellar catalysis to reduce organic solvent use.
Process intensification
Consider flow chemistry for hazardous reagents (e.g., DIAD/DEAD in Mitsunobu) to reduce inventory and improve heat/mass transfer.
Note: These are general green chemistry recommendations; confirm compatibility with your specific transformation and performance targets.
Pharmaceutical Uses
Formulation/excipient status
Not used as a pharmacopeial buffer or common excipient. No compendial grade is indicated for this item.
Relevance in pharmaceutical R&D (general)
Serves as a synthetic building block. The α-hydroxy ketone can be diversified to generate analog libraries; the aryl bromide allows late-stage cross-coupling to install heteroaryl or alkyl groups.
Phenacyl derivatives can function as photolabile protecting groups in preclinical discovery settings (e.g., controlled release of acidic functionalities), typically after converting the alcohol into esters/carbonates.
Manufacturing considerations
If used in GMP-related routes, establish fate-and-purge studies for residual brominated aromatics. Validate analytical methods (HPLC/GC, residual solvents, elemental impurities) and follow ICH guidelines.
No therapeutic or clinical claims are made. For any regulated application, source-grade, residual solvent limits, and impurity profiles must be verified on the lot-specific CoA/Spec Sheet.
Physical Properties
Item-specific specifications (this product)
Melting point, boiling point, density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values for the class/analog
Physical state: typically a low-melting solid or viscous oil for phenacyl alcohols; ring bromination often increases crystallinity (literature, qualitative).
Solubility: expected good solubility in common organic solvents (DCM, EtOAc, THF, MeOH, acetonitrile); limited water solubility due to aryl core (literature, qualitative).
Partitioning: α-hydroxy ketones show moderate polarity; m-bromo increases hydrophobicity vs unsubstituted phenacyl alcohol (literature trend).
Hygroscopicity: α-hydroxy ketones can slowly absorb moisture and form hydrogen-bonded aggregates; minimize prolonged exposure to humid air (general observation).
Thermal behavior: avoid prolonged heating near melting range to prevent self-condensation or dehydration in strongly acidic/basic media (literature caution for acyloins).
Important
Do not treat any literature values above as product specifications. For method development and QC, confirm exact values on the product’s CoA/Spec Sheet.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades for this material (general guidance)
Research grade: Suitable for most synthetic and analytical research. Trace impurity limits (water, residual solvents, metals) vary by lot; check CoA when moisture-sensitive transformations (e.g., Mitsunobu, acyl chloride formation) are planned.
Chromatography/HPLC grade (if applicable): Emphasizes low UV background and minimal non-volatile residues—useful if the compound is deployed as a standard or in photochemical studies. Verify absorbance profile on CoA.
Stabilizers: None specified for this item. If a stabilizer is used in any lot, it will be declared on the CoA; stabilizers can influence downstream reactions (e.g., acid/base-catalyzed steps).
Recommended QC checks before critical use
Identity: 1H/13C NMR (look for benzylic CH2OH and carbonyl signals), HRMS, and IR (strong C=O ~1680–1715 cm−1; broad O–H) (literature, general ranges).
Purity: HPLC/GC and melting range if crystalline (method as per internal SOPs). Residual solvent screening if used in photochemistry.
For exact acceptance criteria, impurities, and analytical data, consult the lot-specific CoA/Spec Sheet.
Reaction and Applications
Functional profile (general literature)
α-Hydroxy ketone (acyloin) adjacent to an aryl ring offers three key handles: carbonyl chemistry, benzylic alcohol derivatization, and aryl bromide cross-coupling (after appropriate transformations if bromine retained).
Representative applications
Phenacyl ester/ether formation (Mitsunobu): The benzylic alcohol can be coupled with carboxylic acids or phenols under Mitsunobu conditions (PPh3/DIAD or DEAD) to form phenacyl esters/ethers that serve as photolabile protecting groups (PPGs) (literature). Meta-bromo substitution tunes absorption and downstream cross-coupling potential.
Oxidation to arylglyoxals: Selective oxidation of the α-hydroxy to a dicarbonyl (glyoxal) using Dess–Martin periodinane, IBX, or TEMPO/bleach systems provides 3-bromophenylglyoxal—useful for heterocycle synthesis (literature).
O–activation and substitution: Conversion of the OH to a leaving group (tosylate/mesylate or halide) enables SN1/SN2 substitutions with N/O/S nucleophiles at the benzylic position; neighboring carbonyl stabilizes carbocation (literature mechanistic insight).
Reductive elaboration: NaBH4 or catalytic hydrogenation can reduce the carbonyl to 1,2-diol; selective reduction or protection permits divergent synthesis (literature).
Cross-coupling of the aryl bromide: The m-bromo substituent can participate in Suzuki, Buchwald–Hartwig, or Sonogashira couplings, enabling late-stage diversification while retaining/transforming the α-hydroxy ketone (literature practice).
Practical tips
Dry, oxygen-free conditions improve yields in Mitsunobu and coupling chemistry.
Protect the alcohol (e.g., as silyl ether) when harsh basic or metal-catalyzed conditions risk competing reactions.
Monitor by TLC/HPLC; UV absorbance from aryl ketone facilitates detection around 254 nm.
Reaction Conditions
General literature-guided conditions for common transformations of 1-(3-bromophenyl)-2-hydroxyethan-1-one (not product specifications)
Mitsunobu coupling to phenacyl esters
Typical: acid (1.0 equiv), alcohol (1.2–1.5 equiv), PPh3 (1.2–1.5 equiv), DIAD/DEAD (1.2–1.5 equiv), solvent THF or toluene, 0–25°C, 2–16 h. Workup with aqueous NaHCO3; yields commonly 60–85% depending on substrate.
Oxidation to arylglyoxal
Dess–Martin periodinane (1.3–1.6 equiv) in DCM (0.05–0.2 M), 0–25°C, 1–3 h; quench with Na2S2O3/NaHCO3. Alternatively, IBX in DMSO or MeCN/H2O with catalytic TEMPO/bleach at 0–10°C. Yields: 55–85% (literature ranges).
Benzylic activation/substitution
Tosylation: TsCl (1.2–1.5 equiv), pyridine or Et3N, DCM, 0–25°C, 2–6 h → benzylic OTs; subsequent SN with amines/thiols in DMF/MeCN, 25–80°C. Carbocation-facilitated substitutions can proceed under milder conditions due to carbonyl stabilization.
Reduction
Carbonyl reduction to diol: NaBH4 (1.1–1.5 equiv) in MeOH/THF at 0–25°C, 0.5–2 h; often gives 1,2-diol mixtures; protect OH groups to control selectivity.
Cross-coupling (aryl bromide)
Suzuki: Ar–Br (1.0 equiv), boronic acid (1.2–1.5 equiv), Pd(PPh3)4 (1–3 mol%), K2CO3 (2–3 equiv), dioxane/H2O (3:1), 60–90°C, 2–12 h. Protect benzylic OH if base-sensitive chemistry is downstream.
Note: Optimize stoichiometry and conditions for your substrate set. Validate dryness (Karl Fischer) and monitor reactions by TLC/HPLC/LC–MS as appropriate.
Safety and Handling
Item-specific hazard data
Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.
General safety considerations for aromatic α-hydroxy ketones (literature/standard practice)
Likely hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. Brominated aromatics can present higher toxicity than non-halogenated analogs (general toxicology trend). Handle as a combustible organic solid.
PPE: Use lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to control vapors/aerosols.
Storage incompatibilities: Keep away from strong oxidizers (risk of exotherm), strong bases or acids (may induce aldol-type reactions, acetalization, or dehydration). Avoid reactive metals and reducing agents that might affect the carbonyl.
First aid (overview, defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical advice for persistent irritation.
Ingestion: Rinse mouth; do not induce vomiting; get medical attention.
Fire-fighting: Use dry chemical, CO2, or foam. Combustion can produce CO/CO2 and HBr/Br-containing fumes; firefighters should wear SCBA.
Spill response: Absorb with inert material (vermiculite), place in chemical waste. Avoid release to the environment.
Authoritative guidance
Always consult the product-specific SDS for definitive hazard classification, exposure limits, and disposal instructions.
Solvent Selection
Solvent behavior (general, literature)
Polarity class: Moderately polar organic compound (α-hydroxy ketone). Capable of hydrogen bonding (donor/acceptor) and π–π interactions.
Expected miscibility/solubility: Good in polar aprotic solvents (DCM, THF, MeCN, DMF, DMSO) and polar protic alcohols (MeOH, EtOH). Limited in water.
Dielectric/partitioning: Will show enhanced solubility as solvent polarity and H-bond basicity increase; ring bromine modestly increases lipophilicity vs phenacyl alcohol.
Selection guidance by use case (practical)
Reaction medium: For nucleophilic substitutions/activations at the benzylic OH, use dry polar aprotic solvents (THF, MeCN, DMF). For Mitsunobu esterifications, THF or toluene with co-solvent DMF is common.
Oxidations to glyoxal derivatives: DCM or MeCN for Dess–Martin/IBX; control water content to suppress over-oxidation (literature practice).
Reductions (NaBH4, catalytic hydrogenation of aryl): Alcoholic solvents (MeOH/EtOH) or mixed MeOH–THF assist reagent solubility; quench carefully due to exotherm.
Purification: Normal-phase silica with gradients of hexanes/EtOAc or DCM/MeOH. The OH group may cause tailing; 0.1–1% TEA can suppress adsorption.
Alternatives and tradeoffs
If avoiding chlorinated solvents, choose 2-MeTHF or EtOAc; expect slower rates for some activations but improved sustainability.
For NMR: CDCl3 typically adequate; DMSO-d6 may be needed if strong H-bonding causes aggregation (literature experience).
Storage and Reconstitution
Item-specific storage/shipping
Storage conditions: Room temperature (per Product Data). Store in a tightly sealed container, in a dry, well-ventilated place away from direct light and heat sources.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance
Protect from moisture: While not strongly hygroscopic, α-hydroxy ketones can hydrogen-bond with water; keep desiccated for optimal stability.
Inert atmosphere: Optional but beneficial for long-term storage to minimize slow oxidation. Include desiccant in the primary or secondary packaging.
Container compatibility: Amber glass recommended to minimize photochemical reactions of the aryl–carbonyl chromophore.
Reconstitution/solution preparation
Insolubility/solubility specifics: Not specified for this item; refer to CoA/Spec Sheet. As general guidance, prepare stock solutions in anhydrous DMSO, MeCN, THF, or EtOAc. Filter through 0.2 µm PTFE if particulate is observed.
Freeze–thaw: If preparing frozen aliquots (e.g., in DMSO), minimize cycles by storing single-use portions at −20°C to −80°C.
Stability checks
Periodically verify identity/purity by HPLC or NMR if stored >12 months at RT.
Always defer to the product label and lot-specific CoA/SDS for definitive storage and handling instructions.
Structure and Identity
Brief overview: 1-(3-Bromophenyl)-2-hydroxyethan-1-one is an aromatic α-hydroxy ketone (a phenacyl alcohol) bearing a bromine at the meta position of the ring. The scaffold combines a deactivated aryl ring with a benzylic α-hydroxy–ketone motif (acyloin), enabling diverse chemoselective transformations.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and composition (general reference; not item specifications)
Common name: 3-bromophenacyl alcohol; 2-hydroxy-1-(3-bromophenyl)ethan-1-one (literature)
Molecular formula: C8H7BrO2 (literature)
Formula weight: ~215.04 g/mol (literature, calculated from elemental composition)
Structural features (general chemistry description)
Functional groups: aromatic bromide; α-hydroxy ketone (benzylic alcohol adjacent to an aryl ketone).
Ring system: monosubstituted benzene (meta-bromo) connected via a carbonyl to a –CH2OH.
2D description: the aryl ring (Br at C3) is bonded to a carbonyl carbon (–C(=O)–), which is alpha to a primary hydroxymethyl (–CH2OH). No stereocenters present; planar aryl and carbonyl with rotatable Ar–CO bond.
Notes
Where exact identifiers (e.g., full InChI, SMILES) are required for informatics, consult the CoA/Spec Sheet to avoid transcription ambiguity.
Synthetic Utility
Key reactivity handles (general literature)
Benzylic α-hydroxy ketone: amenable to oxidation (→ arylglyoxal), reduction (→ 1,2-diol), acylation/silylation (protect OH), or activation (tosylation/halogenation) to enable substitution.
Aryl bromide: enables cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira) to introduce diversity while preserving the α-hydroxy ketone.
Named/representative transformations
Mitsunobu esterification/etherification: Converts the alcohol to phenacyl esters/ethers (PPG precursors).
Dess–Martin or IBX oxidation: Selective conversion to 3-bromophenylglyoxal, a versatile 1,2-dicarbonyl for heterocycle assembly (imidazoles, oxazoles) via condensations.
Tosylation/mesylation → substitution: Formation of benzylic sulfonates that undergo displacement by N-, O-, S-nucleophiles or intramolecular cyclization.
Protecting group choreography: TBS/TBDPS silyl protection of OH to navigate basic couplings; acetalization of the carbonyl if benzylic chemistry is targeted.
Cross-coupling diversification: Install heteroaryl boronates (Suzuki), alkynes (Sonogashira), or amines (Buchwald–Hartwig) before or after manipulating the α-hydroxy site; meta substitution reduces ortho/para directing complications in SEAr steps.
Retrosynthetic value
The molecule arises from 3-bromoacetophenone reduction (e.g., NaBH4) or acyloin strategies. Its central position in divergent synthesis makes it a practical hub for SAR exploration.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and does not have antigen/epitope specificity, clone information, isotype, or species reactivity.
For biochemical targeting studies, any selectivity or binding data must be generated empirically for the intended assay. No item-specific target data are provided.
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.
