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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Point de fusion (°C)
102-106 °C
Poids moléculaire
238.240 g/mol
XLogP3
1.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Exact Mass
238.084 Da
Monoisotopic Mass
238.084 Da
Topological Polar Surface Area
72.800 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
276.000
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
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Application Protocols
Not applicable. No biological assay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block.
For synthetic use, general procedures are provided under Reaction Conditions and Synthetic Utility.
For analytical preparation (general): dissolve a known amount in HPLC-grade MeOH, ACN, or DMSO to prepare 1–10 mg/mL stock; filter (0.2 µm PTFE) before injection to LC/LC–MS. Item-specific solution stability: Not specified; verify experimentally.
Biological Roles
This product is intended for research use in synthetic and analytical chemistry and is not a biomolecule or reagent with intrinsic biological function.
Biological function: Not typically assigned. As an aromatic carboxylic acid/ketone, it does not have a defined role in metabolism or signaling.
Biochemical utility (general): electron-rich aryl ketones absorb in the UV, which can be leveraged for UV-based detection in biochemical assay development or chromatographic method validation, but the compound itself is not a buffer or biochemical cofactor.
Research use restriction (from Product Data): For research use only.
No clinical or therapeutic claims are made or implied. Any evaluation of bioactivity would be purely exploratory and outside the scope of typical catalog use.
Buffer Applications
Not typically applicable. 3-(2′,5′-Dimethoxybenzoyl)propionic acid is an aromatic carboxylic acid used as a synthetic building block, not a defined buffering agent.
If a buffered environment is required for a transformation (e.g., bioconjugation after converting to an active ester), select a buffer compatible with the reaction (e.g., phosphate or bicarbonate), but the compound itself is not used to prepare standard biochemical buffers.
Buffer specifications (pKa, buffering range, recipes) for this item: Not applicable.
Green Alternatives
Greener practice for handling and transforming aryl carboxylic acids focuses on solvent substitution, milder reagents, and minimized protecting-group manipulations.
Prefer greener solvents:
Replace DCM with EtOAc or 2‑MeTHF for extractions and reactions when solubility allows.
Use 2‑MeTHF or CPME instead of THF for enolate chemistry (higher boiling point, partial water tolerance, biomass-derived source for 2‑MeTHF).
Favor acetone or ethanol for recrystallization over halogenated solvents.
Coupling and activation:
Employ catalytic esterification (Amberlyst-15, Sc(OTf)3) or green dehydrative couplings (e.g., COMU in EtOAc/MeCN) instead of DCC/DCM systems to reduce urea waste and chlorinated solvent use.
For acid chlorides, consider T3P (propylphosphonic anhydride) or CDI to avoid thionyl/oxalyl chlorides when compatible with downstream chemistry.
Energy and waste reduction:
Microwave-assisted esterification or amidation in green solvents can shorten reaction times and reduce energy input.
Telescoping: form ester or amide in situ and proceed to subsequent transformations without isolation to cut solvent and materials footprint.
Trade-offs (balanced view):
2‑MeTHF and CPME can exhibit peroxide formation over time; incorporate peroxide testing and inhibitor management. CPME is less polar than THF, potentially affecting enolate reactivity/selectivity.
EtOAc has higher water miscibility than DCM at scale, which can complicate phase splits; salting-out or co-solvent strategies may be needed.
Item-specific green profile: Not specified for this item; refer to CoA/Spec Sheet for any sustainability notes.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item.
Item-specific pharma/formulation information: Not specified for this item; refer to CoA/Spec Sheet.
General context: Aromatic carboxylic acid building blocks like this are commonly used in medicinal chemistry for SAR exploration, intermediate formation (esters, amides), and scaffold elaboration due to their tunable electronics (methoxy substituents) and functional-group handles (ketone and acid).
Formulation note (general): When used as an intermediate, conversion to esters or amides can improve solubility or stability for subsequent steps. For analysis, solutions are typically prepared in DMSO, MeOH, or acetonitrile for LC/LC–MS characterization.
This product is for research use only and is not intended for human or veterinary use.
Physical Properties
Item-specific physical constants are not provided in the Product Data.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions (from Product Data): Room temperature. Shipped under normal conditions.
General/literature expectations for this class (clearly non-spec for this item):
Phase: typically a crystalline solid for aryl‑substituted benzoylpropionic acids.
Acidity: the terminal –CO2H is a weak acid (typical pKa for benzylic aliphatic carboxylic acids ~4–5; literature, general range).
Polarity/solubility: expected to be sparingly soluble in water; soluble in polar organic solvents (e.g., alcohols, acetone) and readily soluble as the carboxylate salt in aqueous base (literature, general behavior of arylalkanoic acids).
Hydrogen bonding: carboxylic acid dimerization in nonpolar media; intramolecular H‑bonding to the ketone is geometrically disfavored (four-atom tether), but weak conformational preferences may occur (general note).
Boiling/melting point, density, refractive index, UV cutoff, and logP: Not specified for this item; refer to CoA/Spec Sheet.
Note: Any precise numerical property (mp, bp, density, solubility limits, UV absorbance, residual water/peroxide/metal levels) should be taken from the item’s CoA/Spec Sheet or SDS; values above are general expectations based on functional groups only.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades (general information to help selection):
Research/technical grade: suitable for routine synthesis and method development. May have broader impurity profiles and is not optimized for trace analysis.
Analytical (AR) grade: tighter specifications for common inorganic and organic impurities; appropriate for quantitative analytical work.
HPLC grade (for solvents): not directly applicable to this solid, but for solution preparation, choose low-UV solvents to minimize baseline noise.
Low-metal/trace grade: relevant if the compound is used in metal-catalyzed cross-coupling; metal contamination can poison catalysts.
Stabilizers/additives:
None specified for this item; refer to CoA/Spec Sheet. Aromatic carboxylic acids of this type typically do not require stabilizers; however, dryness and exclusion of strong light/oxidants help retain integrity.
Quality control considerations (general):
Identity: Confirm by 1H/13C NMR (diagnostic aromatic and methoxy resonances; carbonyls ~170–200 ppm), IR (broad OH ~2500–3300 cm−1; C=O bands: aryl ketone ~1660–1690 cm−1; acid ~1700–1725 cm−1), and HRMS.
Purity: HPLC/UPLC with diode-array detection is effective due to UV activity of the aryl ketone. Water content by Karl Fischer if needed.
Item-specific specs (water, residual solvents, UV cutoff, metals): Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
As a 3-(arylbenzoyl)propionic acid bearing two methoxy substituents, this compound serves as a versatile intermediate in aromatic and carbonyl chemistry.
Key application themes (literature/general):
Enolate chemistry at the methylene adjacent to the aryl ketone (–CO–CH2–):
Deprotonation with LDA, NaHMDS, or KHMDS in THF/2‑MeTHF at −78 to 0 °C enables C‑alkylation or acylation, installing substituents α to the aryl ketone.
Subsequent intramolecular condensations can forge cyclic scaffolds (e.g., tetralone-like frameworks) after functionalization.
Carboxyl functional group interconversions:
Esterification (Fischer with ROH/H+; Steglich with DCC/DMAP) to provide handling-friendly esters.
Conversion to acid chlorides (SOCl2, oxalyl chloride) for amide coupling or Friedel–Crafts acylation on other aromatics.
Amide formation using carbodiimides (EDC/HOBt), uronium salts (HATU, TBTU), or mixed anhydrides.
Electrophilic aromatic modulation:
The 2,5-dimethoxy pattern is strongly activating/ortho‑/para‑directing, enabling selective electrophilic substitutions elsewhere on the ring if protection of the acid is in place.
Cyclization strategies (literature precedents):
Intramolecular aldol or Dieckmann-type variants on suitably derivatized esters can deliver cyclopentanone/cyclohexanone motifs linked to the anisyl ring.
Building block for heterocycles:
The γ‑keto acid can participate in decarboxylative couplings or form pyrones after activation under dehydrative conditions (substrate/condition specific).
Manufacturer applications: Not specified in Product Data; the above reflect general uses of aryl‑substituted benzoylpropionic acids with electron-rich rings.
Reaction Conditions
General literature guidance for transformations of aryl benzoylpropionic acids; not item-specific specs.
Enolate formation/alkylation:
Base: LDA or NaHMDS (1.1–1.5 equiv) in THF or 2‑MeTHF.
Temperature: −78 to 0 °C for deprotonation; 0 to rt for electrophile addition.
Electrophiles: primary alkyl halides, acyl chlorides (to form 1,3‑diketone esters), or aldehydes (aldol additions).
Esterification (Fischer):
ROH (MeOH/EtOH, solvent and reagent), catalytic H2SO4 or p‑TsOH, reflux 2–16 h; remove water azeotropically (Dean–Stark in toluene for higher alcohols).
Steglich esterification:
DCC (1.1 equiv), catalytic DMAP (0.1 equiv), CH2Cl2 or EtOAc, 0 °C→rt, 2–18 h; filter off DCU.
Amide coupling:
HATU or EDCI/HOBt in DMF/MeCN with DIPEA (2–3 equiv), 0 °C→rt, 2–16 h; monitor by LC–MS.
Ketone chemoselective reduction:
Luche conditions: NaBH4 (1.2 equiv), CeCl3·7H2O (0.5 equiv) in MeOH at 0 °C→rt, 0.5–2 h to reduce the aryl ketone preferentially.
Oxime formation:
NH2OH·HCl (1.5 equiv), pyridine or EtOH with base at rt→reflux, 2–6 h; isolate oxime for further rearrangement studies.
Workup/analysis (general):
Acidic extractions partition the neutral acid into organic layers; basic washes form water-soluble carboxylate salts (useful for separations from neutral/aromatic byproducts).
Strong UV absorbance at ~254 nm facilitates TLC/HPLC monitoring.
Exact conditions and yields depend on substitution/electrophiles; optimize on small scale.
Safety and Handling
GHS classification, signal word, pictograms, H‑statements: Not specified for this item; consult the SDS for authoritative hazard information.
General hazards (functional-group based, literature):
Carboxylic acids can be irritants to skin, eyes, and respiratory tract; aryl ketones may cause irritation upon contact or inhalation of dust.
Dust may be combustible; avoid dust formation and ignition sources (standard lab caution for organic solids).
PPE recommendations (good laboratory practice):
Use lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to minimize dust exposure.
Handling tips:
Avoid prolonged exposure to moisture and strong bases unless forming salts intentionally; neutralization generates heat and CO2 (if bicarbonate used).
Avoid strong oxidizers; aromatic ethers (methoxy groups) and benzylic frameworks may be susceptible to harsh oxidative conditions.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with copious water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Incompatibilities (general): strong oxidizers, strong bases/acids for storage, and acylation catalysts that may react with the acid moiety without control.
Fire safety: Use CO2, dry chemical, or foam; combustion may produce CO/CO2 and irritant fumes; firefighters should wear SCBA.
Always consult the product-specific SDS for definitive classifications and measures.
Solvent Selection
This item is an aromatic carboxylic acid with an additional aryl ketone and two methoxy groups, leading to moderate polarity and strong UV absorbance.
Polarity/miscibility (general expectations):
Poorly soluble in water in the neutral form; readily soluble as the carboxylate in aqueous base.
Good solubility in polar organics (MeOH, EtOH, iPrOH, acetone, acetonitrile, DMF, DMSO); limited solubility in nonpolar solvents unless esterified or warmed.
Dielectric considerations: For reactions involving enolates or coupling, use polar aprotic solvents (THF, 2‑MeTHF, CPME, DME, DMF, DMSO, MeCN) to stabilize anions (general guidance).
UV detection: The aryl ketone chromophore supports strong absorbance near 254 nm; choose HPLC solvents with low UV background when monitoring reactions or performing preparative chromatography.
When to choose protic vs aprotic:
Protic (MeOH/EtOH): for Fischer esterification or salt formation; also useful for recrystallization.
Aprotic (THF/2‑MeTHF/EtOAc/MeCN): for enolate chemistry, acyl activation, or amide couplings.
Solvent comparison (general):
THF vs 2‑MeTHF: similar polarity; 2‑MeTHF offers improved sustainability and salting‑out extraction advantages.
EtOAc vs DCM: EtOAc is greener and often dissolves aryl acids sufficiently; DCM may be used for rapid extractions but is less sustainable.
Note: Solubility limits and exact solvent choices are substrate- and base-dependent; verify on small scale. Item-specific solubility is Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Storage (from Product Data): Room temperature. Shipped under normal conditions.
Container: Store in a tightly closed container, protected from moisture and incompatible reagents (oxidants, strong bases/acids). Use desiccant and ambient darkness to minimize hydrolysis or oxidative discoloration over long storage.
Stability (general): Aromatic carboxylic acids with methoxy substituents are typically stable at ambient conditions. Avoid prolonged exposure to strong light/heat. Item-specific retest/expiry: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution/dissolution (general guidance for lab use):
Readily prepares stock solutions in DMSO, DMF, MeOH, or ACN. Gentle warming (30–40 °C) and sonication can aid dissolution.
For aqueous work, dissolve in a small volume of organic co-solvent or convert to a sodium/potassium salt with dilute base, then dilute with water or buffer.
Filter solutions (0.2 µm PTFE) for analytical use. Store solutions at 2–8 °C and use fresh when possible; avoid repeated freeze–thaw.
Research use note: For research use only (from Product Data).
Structure and Identity
3-(2′,5′-Dimethoxybenzoyl)propionic acid is an aromatic benzoylpropionic acid derivative bearing two methoxy substituents on the benzene ring.
Core motif: a 2,5-dimethoxy-substituted phenyl ring acylated with a 4-oxobutanoic acid fragment (Ar–CO–CH2–CH2–CO2H).
Functional groups: one aromatic ring, two aryl methoxy substituents (electron-donating, ortho/meta pattern), one aryl ketone (benzoyl), and one terminal carboxylic acid.
Conjugation: aryl ketone is conjugated with the aromatic ring; the carboxylic acid is separated by a two‑carbon spacer (γ-keto acid topology).
Stereochemistry: none (achiral as drawn; no stereocenters).
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
2D structure in words (general): a benzene ring bearing methoxy groups at the 2- and 5-positions relative to an acyl substituent at the 1-position; the acyl chain is –C(=O)–CH2–CH2–CO2H.
Synthetic Utility
Functional features enabling diverse transformations (literature/general):
Bifunctional reactivity:
Carboxylic acid: amenable to esterification, amidation, acid chloride formation, anhydride formation, decarboxylative couplings (upon activation), and salt formation.
Aryl ketone: supports enolate generation at the α‑position, oxime/hydrazone formation, and reductive transformations to secondary alcohols (NaBH4/Luche, catalytic hydrogenation).
Electron-rich aryl ring (2,5-dimethoxy):
Strongly activating, directing further electrophilic substitution. Methoxy groups can serve as temporary directing groups and can sometimes be demethylated (BBr3, AlCl3/thiols) for phenol access.
Retrosynthetic value:
Serves as a masked 1,4‑dicarbonyl synthon; after esterification, intramolecular condensation can yield five- or six-membered carbocycles.
The acid can be converted to an N‑acyl imidazole or mixed anhydride to enable mild couplings with nucleophiles that are base-sensitive.
Representative named strategy connections:
Steglich esterification (DCC/DMAP), Yamaguchi macrolactonizations (after suitable elaboration), and HATU/EDC couplings for amides.
Luche reduction for chemoselective ketone reduction in the presence of an acid (NaBH4/CeCl3).
Oxime formation (NH2OH·HCl, pyridine/EtOH) as a handle for Beckmann rearrangement on suitably substituted derivatives.
These utilities make the compound a practical convergence point in routes to anisyl-substituted ketones, acids, and cyclic motifs.
Target Specificity
Not applicable. This product is a small-molecule building block and not a biological targeting reagent (no antigen/epitope, clone, or isotype). Item-specific immunoassay targeting data: Not applicable.
Foire aux questions
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 1084-74-8, the molecular formula is C12H14O5, and the molecular weight is 238.24 g/mol. InChIKey HSFBDVDTGCGJBZ-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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