1-Hydroxy-1-phenyl-2-propanone - ≥95% , CAS No.90-63-1

CAS: 90-63-1 Cat. No.: H695092 Fórmula: C₉H₁₀O₂ Peso molecular: 150.17 Número EC: 202-006-0

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥95%

Nombres e identificadores

Sonrisas canónicas

CC(=O)C(C1=CC=CC=C1)O

IUPAC Name

1-hydroxy-1-phenylpropan-2-one

InChIKey

ZBFFNPODXBJBPW-UHFFFAOYSA-N

INCHI

1S/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3

Isómeros SMILES

CC(=O)C(C1=CC=CC=C1)O

Peso molecular

150.17

Reaxy-Rn

3196936

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3196936&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Phenylpropanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Phenylpropanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpropanes
• Alternative Parents: Acyloins Alpha-hydroxy ketones Secondary alcohols Organic oxides Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenylpropane - Acyloin - Alpha-hydroxy ketone - Secondary alcohol - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic alcohol - Organooxygen compound - Carbonyl group - Alcohol - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
• 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

Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 150.170 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068 Da
• Monoisotopic Mass: 150.068 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 136.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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

• Not applicable as a biological reagent. No WB/IHC/IF/FC protocols or recommended dilutions are associated with this small-molecule chemical.
• For synthetic uses, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory protocols and optimization guidance.

Biological Roles

• Item-specific biological data are not provided; this product is designated for research use only.

• General context (literature):

  • α-Hydroxy aryl ketones occur as intermediates in oxidative metabolism of alkylbenzenes and can be accessed enzymatically (e.g., via alcohol dehydrogenases or Baeyer–Villiger/ketoreductase cascades). However, 1-hydroxy-1-phenyl-2-propanone itself is predominantly a synthetic intermediate in laboratory chemistry.
  • The α-hydroxyl adjacent to a carbonyl can engage in hydrogen bonding with proteins/enzymes and can chelate metals transiently; such interactions underpin biocatalytic transformations (e.g., lipase-mediated resolutions), but no specific biological pathway or role is assigned to this exact compound.
  • Chirality at the α-carbon allows for stereospecific enzyme recognition where applicable; enantioselective biocatalysis has been reported broadly for related α-hydroxy ketones.

• Note: No clinical, diagnostic, or therapeutic use is implied; for laboratory research only.

Buffer Applications

• Not typically applicable. 1-Hydroxy-1-phenyl-2-propanone is an organic building block and is not used as a buffering agent.
• For aqueous operations involving this compound, choose buffer systems compatible with your reaction or extraction chemistry (e.g., phosphate, acetate) to control pH during oxidations/reductions or enzymatic resolutions, but the compound itself does not serve as a buffer.

Green Alternatives

• Context: As a building block, greener choices concern solvents, reagents, and energy input rather than replacing the molecule itself.

• Greener solvent choices (general guidance):

  • Prefer EtOAc, MeTHF, CPME, 2-propanol, MeCN (with care), or water/EtOH mixtures where compatible.
  • Reduce reliance on chlorinated solvents (CH2Cl2, CHCl3) unless necessary for selectivity.

• Greener oxidation/reduction options (literature):

  • Oxidations: Use catalytic TEMPO with aqueous bleach (NaOCl), or O2 with nitroxyl catalysts, in biphasic systems with minimal organic solvent.
  • Reductions: Employ catalytic hydrogenation (H2, Pd/C) or transfer hydrogenation (isopropanol/Ru or organocatalytic systems) instead of stoichiometric metal hydrides when feasible.

• Energy/processing:

  • Consider flow chemistry for hazardous oxidants, enabling lower inventory and improved heat/mass transfer.
  • Employ solvent recycling and distillation; design crystallization-based purifications to minimize silica waste when possible.

• Example comparison (general):

  • Traditional oxidation (Dess–Martin in CH2Cl2) vs. greener alternative (TEMPO/NaOCl in EtOAc–buffer): similar conversions reported in literature with reduced waste and improved E-factor, albeit with careful pH control and potential halogenation side-reactions if not optimized.

Pharmaceutical Uses

• Item-specific pharmacopeial status, excipient grade, or GMP suitability: Not specified for this item; refer to CoA/Spec Sheet.

• General context (no therapeutic claims):

  • α-Hydroxy aryl ketones like 1-hydroxy-1-phenyl-2-propanone are used as synthetic intermediates in medicinal chemistry programs to build β-aryl alcohols, 1,2-diols, enones, and heterocycles.
  • The chiral center enables SAR exploration through enantioenriched variants prepared by chiral resolution or asymmetric synthesis/biocatalysis.
  • In formulation science, this specific compound is not a common excipient; its utility is upstream in route development, not as a finished formulation component.

Physical Properties

• Item-specific (from Product Data):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage conditions: Room temperature (as provided).

• Literature/typical values for 1-hydroxy-1-phenyl-2-propanone (for general reference only; not item specifications):

  • Physical state: typically a colorless to pale yellow liquid or low-melting solid depending on purity and temperature (literature).
  • Density, refractive index, boiling/melting points, UV cutoff, residual water/peroxide/metal content: Not specified here; consult literature or CoA/SDS for definitive values for the supplied lot.
  • Solubility: expected to be miscible with many organic solvents (e.g., EtOAc, MeOH, CH2Cl2, acetone); moderate water solubility due to the α-hydroxyl and carbonyl (literature, qualitative).
  • Partitioning: aromatic α-hydroxy ketones typically show intermediate polarity; logP expected in the low-to-moderate range (literature, qualitative).

• Practical notes (general):

  • As an α-hydroxy ketone, it may exhibit hydrogen bonding and can form intramolecular H-bonds that influence NMR chemical shifts and chromatographic behavior.
  • The compound is chiral; racemic mixtures may display broadened or doubled signals in chiral solvating agents.

Quality and Grades

• Item-specific information from Product Data:

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

• Guidance for interpreting grade (general):

  • If offered in synthetic/technical grade, expect suitability for general organic synthesis; UV background and trace metal limits may be unqualified.
  • If offered as ≥95–99% assay (typical for fine chemicals), expect low levels of starting materials/side-products; exact impurity profile should be confirmed on CoA/GC/HPLC.
  • HPLC/GC grade labeling typically implies low non-volatile residue and low UV absorbance suitable for analytical use; absent here unless explicitly stated on the label/CoA.

• Practical QA/QC recommendations (general):

  • Verify identity by 1H/13C NMR and MS; an α-hydroxy ketone will show a characteristic deshielded α-proton (CHOH) and a carbonyl signal ~δC 200 ppm.
  • Check for oxidation to the corresponding α-diketone (e.g., phenylglyoxal derivatives) by LC/MS if material is aged.
  • Water content and residual solvents: Not specified for this item; refer to CoA/Spec Sheet. Use Karl Fischer and GC if process-critical.

Reaction and Applications

• Role: 1-Hydroxy-1-phenyl-2-propanone is an α-hydroxy aryl methyl ketone (acyloin type) useful as a chiral (racemizable) building block and synthon in fine-chemical synthesis.

• Typical applications (literature/general):

  • Oxidation to α-diketones (e.g., phenylglyoxal derivatives) using Dess–Martin periodinane, TEMPO/bleach variants, or MnO2; useful in heterocycle construction and as electrophiles in nucleophilic additions.
  • Ester/carbonate/silyl protection of the α-hydroxyl (Ac2O, BzCl, Boc2O for carbonates; TBSCl/TBDPSCl) to modulate reactivity and enable selective transformations at the carbonyl.
  • Nucleophilic additions at the carbonyl (NaBH4, catalytic hydrogenation) giving β-aryl-1,2-diols; subsequent selective derivatizations furnish diverse scaffolds.
  • Dehydration to enones (E1cB under acidic or basic conditions) yielding aryl-substituted α,β-unsaturated ketones; these serve as Michael acceptors for further elaboration.
  • Halogenation at the α-position (NBS/NCS, under radical or ionic conditions) after protection of the OH; enables substitution or cyclization sequences.
  • Asymmetric transformations: resolution or enantioselective acylation/oxidation using organocatalysts or lipases (e.g., Candida antarctica lipase B) to access enantioenriched α-hydroxy ketones.

• Practical tips:

  • Control of stereochemistry: racemization can occur under basic/acidic conditions; maintain mild pH and lower temperatures where stereointegrity matters.
  • Workup: owing to H-bonding, product may tail on silica; mild base or small alcohol fractions help elution.
  • Monitoring: TLC with UV 254 nm typically effective; stain with phosphomolybdic acid or anisaldehyde to visualize hydroxyl-containing spots.

Reaction Conditions

• General literature guidance (not item specifications; optimize per substrate and scale):

  • Oxidation to α-diketone: Dess–Martin periodinane (1.3–1.5 equiv) in CH2Cl2, 0–25 °C, 1–3 h; typical conversions high with minimal over-oxidation when base is limited. Alternatively, TEMPO (5–10 mol%) with NaOCl (pH ~9) in biphasic EtOAc/NaHCO3(aq), 0–10 °C.
  • Reduction to 1,2-diol: NaBH4 (1.1–2.0 equiv) in MeOH or EtOH at 0–25 °C, 0.5–2 h; diastereoselectivity solvent-dependent. Catalytic hydrogenation (H2, 1–3 bar, Pd/C 5–10 wt%) in EtOH or EtOAc at rt–40 °C can effect clean reduction.
  • Protection (TBS ether): TBSCl (1.2–1.5 equiv), imidazole (2–3 equiv), DMF or CH2Cl2, 0–25 °C, 2–6 h; monitor by TLC. Acetylation: Ac2O (1.5 equiv), pyridine or DMAP (cat.), CH2Cl2, 0–25 °C.
  • Dehydration to enone: catalytic p-TsOH in toluene or Dean–Stark with azeotropic water removal, or POCl3/pyridine at 0–25 °C; control to avoid overreaction/polymerization.
  • α-Halogenation (after OH protection): NBS (1.05 equiv) with AIBN (cat.) in CCl4/MeCN under hv or thermal initiation; or ionic conditions with NCS/NBS in AcOH at 0–10 °C.

• Monitoring and workup:

  • Use TLC (UV 254 nm) and LC/MS for endpoint. Quench oxidants carefully; for DMP, quench with Na2S2O3/NaHCO3 and filter.
  • Maintain anhydrous conditions where carbocationic rearrangements or acyl transfer might occur.

• Expected yields:

  • Many of the above transformations report moderate to high isolated yields in the literature (often 60–90%), subject to catalyst, solvent, and substrate-specific effects.

Safety and Handling

• Item-specific hazard information: Signal word, H-statements, GHS classification, and pictograms are not provided for this item; defer to the product SDS for authoritative safety information.

• General safety guidance for α-hydroxy aryl ketones (literature/industry practice):

  • Likely hazards: may cause skin/eye irritation; avoid inhalation of vapors or mists and prevent prolonged skin contact. Handle in a fume hood.
  • PPE: laboratory coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use respiratory protection if ventilation is inadequate.
  • Incompatibilities: strong oxidizing agents (risk of exothermic oxidation), strong bases or acids (may catalyze aldol-type condensations, dehydration, or cleavage). Avoid reactive metals if moisture/base is present.
  • Thermal/photochemical behavior: α-hydroxy ketones can undergo oxidation to α-diketones; minimize exposure to air/heat if oxidation is a concern. Not a typical peroxide former, but periodic assessment for degradation is prudent.
  • First aid (overview; consult SDS):
    • Inhalation: move to fresh air; seek medical attention if symptoms persist.
    • Skin: wash with soap and water; remove contaminated clothing.
    • Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
  • Spill response: absorb with inert material (vermiculite, sand), collect for disposal. Prevent release to drains.
  • Waste: dispose in accordance with local regulations; typically treat as organic chemical waste.

Solvent Selection

• Applicability: This product is an organic building block/intermediate rather than a solvent. Solvent choice here concerns its use in reactions, workups, and analyses.

• General solvent compatibility (literature/experience):

  • Polar protic/aprotic organic solvents (MeOH, EtOH, i-PrOH, MeCN, DMF, DMSO, EtOAc, THF, CH2Cl2) typically dissolve α-hydroxy aryl ketones readily.
  • Water solubility is moderate; salting-out facilitates phase separations during workup.
  • For chromatographic purification, normal-phase silica using EtOAc/hexanes or gradient to MeOH works; the OH group may cause tailing—add 0.1–1% triethylamine if needed.

• Selection guidance by task (general):

  • Nucleophilic substitutions/derivatizations (e.g., acylation, silylation): CH2Cl2, THF, or MeCN under anhydrous conditions.
  • Oxidations to α-dicarbonyls: Acetonitrile, acetone, or MeOH often used; choose based on oxidant compatibility.
  • Reductions to 1,2-diols or deoxygenation: Protic solvents with hydride sources (MeOH/i-PrOH) or ether solvents with borohydrides/hydrosilanes.
  • Asymmetric catalysis on the α-position: Toluene, CH2Cl2, or ethers are common for organocatalysts/metal catalysts.

• Notes:

  • Avoid strongly basic aqueous media if racemization or retro-aldol pathways are concerns.
  • Dry solvents when moisture-sensitive steps (e.g., acylation/silylation) are performed.

Storage and Reconstitution

• Item-specific storage/shipping:

  • Storage: Room temperature (as provided in Product Data). Protect from light and moisture for best stability.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General handling recommendations:

  • Keep container tightly closed under inert headspace (e.g., nitrogen) if long-term storage is anticipated to minimize aerial oxidation to α-dicarbonyl species.
  • If solidification occurs at lower temperatures, gently warm to ambient and mix thoroughly before use.
  • Avoid repeated freeze–thaw or heat cycles; subdivide into aliquots for sensitive applications.

• Reconstitution:

  • Not applicable; supplied neat as a liquid/solid reagent (appearance not specified). If a solution is required, prepare fresh in a compatible dry solvent (e.g., CH2Cl2, EtOAc, MeOH) at the desired concentration.

• Shelf-life/quality checks:

  • Periodically assess purity by NMR/GC/LC as needed for critical applications. Any specific shelf-life, stabilizers, or acceptance criteria: Not specified for this item; refer to CoA/Spec Sheet.

• Research Use Note: For research use only.

Structure and Identity

• Item-specific (from Product Data):

  • Product name: 1-Hydroxy-1-phenyl-2-propanone (SKU: H695092)
  • CAS: 90-63-1
  • PubChem CID: 92733
  • InChIKey: 452329 (as provided; verify against SDS/CoA)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (general reference, not item specifications):

  • A commonly referenced structure for 1-hydroxy-1-phenyl-2-propanone corresponds to an α-hydroxy ketone bearing a phenyl on the α-carbon adjacent to an acetyl group (Ph–CH(OH)–CO–CH3).
  • Typical molecular formula: C9H10O2 (literature)
  • Typical molecular weight: ~150.18 g/mol (literature)

• Structural features (general):

  • Functional groups: one secondary alcohol (α-hydroxyl) adjacent to one aryl-substituted ketone (α-hydroxy aryl methyl ketone).
  • Ring systems: one benzene ring (phenyl) directly bonded to the α-carbon of the carbonyl fragment.
  • Stereochemistry: the α-carbon bearing OH is stereogenic; materials may be racemic unless otherwise specified (no stereochemical specification is provided for this item).
  • 2D description: a phenyl substituent and a hydroxyl substituent reside on the same α-carbon next to a methyl ketone; conjugation between the aryl ring and carbonyl is possible via the α-carbon.

Synthetic Utility

• Functional group synopsis: aromatic ring (electrophilic substitution platform), secondary α-hydroxyl (nucleophilic and directing), and methyl ketone (electrophilic carbonyl and enolizable α-position).

• Transformations (literature/general):

  • Protection/deprotection: silyl (TBS, TBDPS), benzoyl/acetyl carbonates; enables orthogonal manipulation of the carbonyl.
  • Oxidation: conversion to α-dicarbonyls (e.g., phenylglyoxal-type) with hypervalent iodine or nitroxyl-catalyzed systems.
  • Reduction: NaBH4 or catalytic hydrogenation to furnish syn/anti 1,2-diols; subsequent selective oxidations or cyclizations build tetrahydrofuran or dioxolane motifs.
  • Dehydration/condensation: acid/base-promoted elimination to enones; conjugate additions expand diversity (Michael additions of amines, thiols, or stabilized carbanions).
  • Cross-coupling leverage: after halogenation or via aryl ring functionalization, Suzuki/Heck/Buchwald steps integrate the motif into larger frameworks.
  • Chiral pool/biocatalysis: kinetic resolution or DKR using lipases or ketoreductases delivers single-enantiomer α-hydroxy ketones as valuable chiral synthons.

• Retrosynthetic value:

  • Disconnection at the C–OH bond suggests access from phenylglyoxal or from α-halo ketones via hydrolysis/reduction; alternatively from acetophenone via α-hydroxylation (e.g., via SeO2 or dioxirane chemistry) followed by methyl migration/acetylation strategies.

Target Specificity

• Not applicable. This product is a small-molecule chemical reagent/intermediate and is not an antibody, probe, or biologic. No target, epitope, clone, isotype, or species reactivity data are associated with this item.