Benzyloxyacetone - ≥95% , CAS No.22539-93-1

CAS: 22539-93-1 Cat. No.: B168757 Summenformel: C₆H₅CH₂OCH₂COCH₃ Molekulargewicht: 164.2 EG-Nummer: 828-028-6

GRADE & PURITY ≥95%

Synonyms

1-(Benzyloxy)propan-2-one | SY107427 | EN300-108880 | Z906195414 | 2-Propanone, 1-(phenylmethoxy)- | SCHEMBL712779 | AKOS009157009 | 1-(benzyloxy)acetone | FT-0622855 | MFCD01863536 | 1-Benzyloxy-2-propanone | 1-[(phenylmethyl)oxy]-2-propanone | 1-Benzylo

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Specifications

Synonyme

1-(Benzyloxy)propan-2-one | SY107427 | EN300-108880 | Z906195414 | 2-Propanone, 1-(phenylmethoxy)- | SCHEMBL712779 | AKOS009157009 | 1-(benzyloxy)acetone | FT-0622855 | MFCD01863536 | 1-Benzyloxy-2-propanone | 1-[(phenylmethyl)oxy]-2-propanone | 1-Benzylo

Spezifikationen & Reinheit

≥95%

Storage

Store at 2-8°C,Argon charged

Verschickt in

Wet ice

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥95%

Namen und Kennungen

• Pubchem Sid: 504762666
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762666
• Kanonisches Lächeln: CC(=O)COCC1=CC=CC=C1
• IUPAC Name: 1-phenylmethoxypropan-2-one
• InChIKey: YHMRKVGUSQWDGZ-UHFFFAOYSA-N
• INCHI: 1S/C10H12O2/c1-9(11)7-12-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
• Isomere SMILES: CC(=O)COCC1=CC=CC=C1
• WGK Deutschland: 3
• Molekulargewicht: 164.2
• Reaxy-Rn: 2046112
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2046112&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzylethers
• Alternative Parents: Ketones Dialkyl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzylether - Ketone - Ether - Dialkyl ether - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
• 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

Chemische und physikalische Eigenschaften

• Brechungsindex: n20/D 1.512 (lit.)
• Flammpunkt (°F): 230 °F
• Flammpunkt (°C): 110 °C
• Siedepunkt (°C): 259 °C (lit.)
• Molekulargewicht: 164.200 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 164.084 Da
• Monoisotopic Mass: 164.084 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 137.000
• 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 assay or bioanalytical application protocols are provided for this small-molecule reagent. For synthetic use, see the Reaction Conditions and Synthetic Utility sections for representative procedures and optimization guidance tailored to common transformations (hydrogenolysis, reductive amination, enolate chemistry). Always consult primary literature for scale-up.

Biological Roles

This product is intended for research and laboratory synthesis. It is not an endogenous metabolite and has no established physiological role. Consequently, there are no specific biological functions to summarize for benzyloxyacetone itself.

General considerations (literature/practice):

• As a small, non-ionic organic molecule bearing an ether and ketone, it may act as a hydrophobic probe or intermediate in the synthesis of bioactive candidates. However, any biological activity would derive from target molecules synthesized from this intermediate, not from benzyloxyacetone per se.
• The benzyl ether serves as a removable protecting group in complex-molecule synthesis (including peptides, oligosaccharides, and natural product fragments), enabling temporary masking of primary alcohols during assembly.

No clinical or therapeutic claims are made or implied. Use strictly for research applications.

Buffer Applications

Not typically applicable. Benzyloxyacetone is a neutral organic reagent (not a buffering agent) and is not used to prepare aqueous buffer systems or electrophoresis buffers. For laboratory use, focus instead on the synthetic utility, reaction conditions, and storage guidance tabs for relevant information.

Green Alternatives

While benzyloxyacetone is a substrate rather than a process solvent, greener choices can be applied to its use in synthesis by selecting safer media and catalysts.

Greener choices for common transformations (literature/practice):

• Hydrogenolysis of Bn ether:
  • Prefer ethanol or 2-propanol over chlorinated solvents; use Pd/C at ambient temperature/pressure where feasible.
  • Flow hydrogenation can improve safety and reduce solvent waste.
• Enolate/aldol chemistry:
  • Use 2-MeTHF or CPME instead of THF/Et2O where compatible; they offer improved safety profiles and biorenewable sourcing (2-MeTHF).
  • Explore organocatalysts (e.g., proline derivatives) to avoid heavy metals for asymmetric variants.

Illustrative comparison (general):

• THF vs 2-MeTHF: similar polarity/solvation for enolates; 2-MeTHF is often less miscible with water (easier workups) and derived from renewable feedstocks; however, enolate reactivity and low-temperature behavior may require re-optimization.
• DCM vs EtOAc: EtOAc is a greener extraction/chromatography solvent but may alter hydrogenolysis kinetics; adjust catalyst loadings accordingly.

Process intensification:

• Solvent recycling, microscale screening to minimize reagent excess, and catalytic hydrogen sources (transfer hydrogenation with i-PrOH) can lower E-factors while maintaining performance.

All choices should be validated for the specific transformation on this substrate.

Pharmaceutical Uses

• Formulation/excipient role: none established. Benzyloxyacetone is not a standard pharmaceutical excipient.
• Typical role in pharma R&D: synthetic intermediate for structure–activity relationship (SAR) exploration, protecting-group strategies, and fragment installation via ketone chemistry (e.g., reductive amination, aldol coupling).
• Compendial status: no pharmacopeial monograph is known for this specific reagent (general note).

Any application in drug development would be as a process intermediate within a GMP framework; specifications, residuals, and impurity controls must be defined per process needs. No therapeutic or clinical use is claimed for this material.

Physical Properties

Item-specific specifications (for this catalog listing):

• Appearance: 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/general properties (for reference; not item specifications):

• Physical state: typically a colorless to pale yellow liquid for many benzylic ethers of similar size.
• Miscibility: expected to be miscible with common organic solvents (e.g., dichloromethane, THF, ethyl acetate, toluene) and only sparingly soluble in water due to the aryl group and moderate polarity of the ether/ketone.
• Polarity: moderately polar aprotic, combining an ether and a ketone; suitable for both nucleophilic and electrophilic transformations.
• Volatility: significantly less volatile than low-boiling ethers; handle with standard liquid-transfer technique (syringe/cannula) when water/air exclusion is desired.
• Odor: mild aromatic/ether-like (qualitative; consult SDS).

Computed/literature identifiers (reference):

• Formula (literature): C10H12O2
• Formula weight (literature): ~164.20 g/mol

Always verify any critical physical parameters (bp, mp, density, refractive index, UV cutoff, water/peroxide content, metal traces) on the specific lot CoA; values are not specified for this item.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for exact assay, impurity profile, and any stabilizers.
• UV cut-off, water content, residual solvents, metals: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret typical grades (general guidance):

• Research or reagent grade typically ensures suitability for routine synthetic operations. For chromatography-sensitive applications (photochemistry, UV detection), low-UV grades or additional purification may be required.
• If a stabilizer is present in some lots of aryl ethers/ketones, it is usually to suppress oxidation/polymerization; verify presence/absence on the CoA, as stabilizers can interfere with downstream steps (e.g., hydrogenations).
• For enolate chemistry or moisture-sensitive couplings, practitioners often perform a quick pre-treatment (e.g., drying over molecular sieves, brief distillation) regardless of listed grade to ensure low water/peroxide levels.

Lot-specific documentation:

• Certificate of Analysis (CoA) provides assay, GC/HPLC purity, and key residuals.
• Specification Sheet details acceptable ranges.
  Please consult these documents for procurement decisions and method validation.

Reaction and Applications

Benzyloxyacetone is a versatile alpha-alkoxy methyl ketone and a benzylic ether, combining two broadly useful synthetic handles. Typical research applications (literature/practice):

• Protecting-group relay:

  • The benzyl ether can be selectively removed by catalytic hydrogenolysis (H2, Pd/C) to afford 1-hydroxy-2-propanone (acetol), leaving the ketone intact. This enables temporary masking of a sensitive alcohol function during multistep sequences.
  • Orthogonality: compatible with many bases, organometallics, and neutral conditions; removable under hydrogenolysis or strong Lewis acid conditions.

• Enolate-derived transformations:

  • The methyl ketone forms enolates/enamines for C–C bond construction (alkylation, aldol, Michael additions). The adjacent –CH2–O–Bn can act as a leaving group under specific conditions, enabling fragmentation or rearrangement chemistry.
  • Stereocontrol: chiral auxiliaries or organocatalysts can be applied to asymmetric aldol or Mannich chemistry on the ketone.

• Reductive amination:

  • Direct conversion to benzyloxy-substituted secondary/tertiary amines using amines and hydride sources (NaBH3CN, NaBH(OAc)3) or H2/Pd. Subsequent hydrogenolysis removes the benzyl to reveal 2-amino-1-propanol motifs.

• Cyclization and acetal chemistry:

  • Under acid catalysis, intramolecular reactions of alpha-alkoxy ketones can deliver cyclic acetals or tetrahydrofuran derivatives; benzylic oxygen substitution adds tunability via later deprotection.

• Functional-group interconversions:

  • Oxime/hydrazone formation at the ketone; Wolff–Kishner or Clemmensen reductions to the ether–propyl framework; Baeyer–Villiger oxidation to the corresponding ester can be explored with appropriate control.

Reaction Conditions

General literature guidance for typical operations on benzyloxyacetone (reference conditions; optimize per substrate and scale):

• Hydrogenolysis of benzyl ether:

  • Catalyst: 5–10% Pd/C (0.5–5 mol% Pd relative to substrate).
  • Solvent: EtOH, MeOH, or EtOAc; optional AcOH (0.1–1 eq) to promote rate.
  • Conditions: H2 balloon to 3 bar; 20–40 °C; 2–24 h.
  • Outcome: cleavage of Ph–CH2–O– to reveal 1-hydroxy-2-propanone with the ketone intact.

• Reductive amination at the ketone:

  • Reagents: amine (1.1–2.0 eq), NaBH3CN (1.2–2.0 eq) or NaBH(OAc)3 in MeOH/EtOH/MeCN with AcOH (pH ~5–6).
  • Temperature: 0–25 °C; 2–16 h.
  • Notes: control water content; post-reaction hydrogenolysis can remove benzyl to unmask aminoalcohols.

• Enolate alkylation:

  • Base: LDA or NaHMDS (1.1–1.5 eq) in dry THF, −78 to 0 °C.
  • Electrophiles: primary alkyl halides, Michael acceptors (via enolate addition), or acylating agents.
  • Quench: aqueous NH4Cl or HOAc; 0–25 °C workup.

• Baeyer–Villiger oxidation:

  • Oxidant: mCPBA (1.2–2.0 eq) in DCM, 0–25 °C.
  • Considerations: monitor for potential ether cleavage under strongly acidic conditions; use buffered mCPBA if required.

Expected yields vary with substrate and conditions; consult primary literature and perform small-scale optimization. Observe appropriate safety for hydrogenation and strong bases.

Safety and Handling

Item-specific hazard statements, signal word, pictograms, and GHS class: Not specified for this item; refer to the SDS for authoritative safety information.

General laboratory safety guidance for benzylic ethers and aliphatic ketones (literature/practice—not product specifications):

• Anticipated hazards: may cause eye/skin irritation and respiratory irritation; ketones and ethers can be harmful if swallowed or inhaled. Avoid aerosol formation and prolonged skin contact.
• PPE: lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (nitrile commonly used). Work in a fume hood.
• Incompatibilities: strong oxidizers (risk of exotherm/oxidation), strong acids or bases (can catalyze cleavage or condensation), and finely divided metals in air.
• Peroxide formation: simple dialkyl ethers are peroxide-formers; benzylic aryl ethers are less prone, but good practice is to store under inert gas as provided and check aged materials if distilled.
• Fire safety: treat as a combustible organic liquid; keep away from ignition sources. Use CO2, dry chemical, or foam for small fires per SDS guidance.
• First aid (overview; defer to SDS): rinse eyes/skin with water for several minutes upon contact; move to fresh air if inhaled; seek medical attention if symptoms persist.
• Handling tips: minimize moisture and oxygen exposure when performing base-sensitive or hydrogenation procedures; use dry glassware and inert atmosphere as needed.

Always consult the product SDS and your institutional EHS protocols before use.

Solvent Selection

This product is a reactive organic building block (benzylic ether bearing a methyl ketone), not a process solvent. Solvent selection is therefore driven by the intended transformation on this substrate rather than by its use as a solvent.

General miscibility and solvent pairing (literature/practice):

• Solubility profile: typically soluble in ethers (THF, MTBE), chlorinated solvents (DCM, chloroform), esters (EtOAc), aromatics (toluene), and polar aprotics (MeCN, DMF). Limited solubility in water.
• Choosing the medium:
  • Enolate chemistry/alkylation: dry THF, DME, or toluene/THF mixtures at −78 to 0 °C with LDA or related bases.
  • Hydrogenolysis of the benzyl ether: MeOH, EtOH, EtOAc, or AcOH-containing media with Pd/C under H2.
  • Reductive amination: alcohols (MeOH/EtOH/i-PrOH) or MeCN; adjust acidity with AcOH; use NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation.
  • Aldol/condensation: toluene, DCM, or MeCN under Lewis/Brønsted acid catalysis.

Comparison notes:

• Versus more hydrophobic benzylic ethers lacking a carbonyl, benzyloxyacetone dissolves better in moderately polar media due to the ketone.
• For aqueous or biphasic catalysis, consider phase-transfer agents (e.g., quaternary ammonium salts) if water compatibility is needed.

Storage and Reconstitution

Item-specific storage and shipping (from Product Data):

• Storage Conditions: Store at 2–8 °C, argon charged.
• Shipped In: Wet ice.
• Research Use: For research use only.

General handling guidance (practice; not item specifications):

• Keep container tightly closed under inert gas (Ar or N2) to limit oxidation or acid-catalyzed side reactions.
• Minimize exposure to moisture and air during transfers (use septum caps and dry syringes/cannulas if conducting base-sensitive chemistry).
• If long-term storage is anticipated, consider aliquoting to minimize repeated headspace exchange.
• Do not freeze unless validated for your workflow (potential glass ampoule stress/phase separation); 2–8 °C per label is recommended.
• Inspect material visually before use; if crystallization, phase separation, or discoloration is observed, warm gently to ambient and verify integrity by GC/HPLC/NMR as appropriate.

Reconstitution: Not applicable; supplied as a neat organic liquid (typical for this class). If dilution is needed for dosing or stock preparation, use anhydrous, oxygen-free solvents compatible with the intended reaction (e.g., dry THF, toluene, MeOH), and label secondary containers with concentration and date.

Structure and Identity

Item-specific identifiers from Product Data:

• CAS: 22539-93-1
• SKU: B168757
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature identity (for reference; not item-specific specifications):

• Common name: Benzyloxyacetone (also called 1-(benzyloxy)-2-propanone; acetonyl benzyl ether)
• Molecular formula (literature): C10H12O2
• Molecular weight (literature): ~164.20 g/mol
• Typical SMILES (literature): CC(=O)COCc1ccccc1 (depicts CH3–CO–CH2–O–CH2–Ph)

Structural features (general description):

• Functional groups: one aryl benzyl ether (Ph–CH2–O–) and one aliphatic methyl ketone (–CO–CH3).
• Connectivity: an ether oxygen bridges a benzylic methylene (–CH2–Ph) and the methylene alpha to a methyl ketone (–CH2–O–CH2–Ph adjacent to –CO–CH3).
• 2D description: a phenyl ring bonded to a benzylic CH2, linked via an ether O to a –CH2– that is alpha to a carbonyl carbon bearing a terminal methyl group.
• Stereochemistry: achiral; no stereocenters.

Note: All non-specified identifiers for this catalog item should be confirmed against the product’s CoA/Spec Sheet prior to use in regulated workflows.

Synthetic Utility

Key functional handles:

• Benzylic ether (Ph–CH2–O–): removable protecting group; stable to many bases and nucleophiles yet cleavable by hydrogenolysis (H2, Pd/C) or strong Lewis/Brønsted acids.
• Methyl ketone (–CO–CH3): supports enolate formation, reductive amination, oxime/hydrazone formation, and oxidative/reductive interconversions.

Representative transformations (literature/practice):

• Hydrogenolysis → 1-hydroxy-2-propanone (acetol), enabling late-stage unmasking of a primary alcohol adjacent to a carbonyl.
• Reductive amination with primary/secondary amines to furnish benzyloxy-substituted amines; subsequent benzyl deprotection yields 2-amino-1-propanol derivatives.
• Enolate chemistry: LDA or NaHMDS-mediated alpha-alkylation/acylation; crossed-aldol reactions under TiCl4, SnCl4, or organocatalysts.
• Baeyer–Villiger oxidation (mCPBA or peracids) to access corresponding esters; choice of reagent governs chemoselectivity vs ether cleavage.
• Chemoselective reductions: NaBH4 or catalytic hydrogenation to secondary alcohol (benzyloxy-2-propanol); Wolff–Kishner/Clemmensen for deoxygenation when compatible.
• Ether manipulations: benzyl migration or cleavage under acidic conditions; conversion to leaving groups after activation at oxygen (e.g., silylation, then substitution in multistep sequences).

Practical notes:

• Maintain inert atmosphere during strong-base steps to avoid side reactions.
• When planning hydrogenolysis, exclude sulfur- or amine-poisoning species from the mixture and pre-filter Pd/C carefully to avoid metal contamination.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting reagent (e.g., antibody, ligand, or probe) with defined antigen/epitope specificity.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.