This compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
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.
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Application Protocols
No antibody/assay application protocols are associated with this small-molecule reagent in the Product Data.
Typical laboratory uses (general, non-protocol)
Synthetic transformations: Follow standard procedures for esterification, amidation, and cross-coupling as outlined in Reaction Conditions.
Analytical: Prepare solutions in ACN/MeOH (often 0.5–2 mg/mL) for LC/UV or LC–MS method development; adjust pH with formic/acetic acid or ammonium buffers depending on ionization requirements.
For any validated, method-specific protocols, refer to your internal SOPs or analytical method files.
Biological Roles
Item-specific
Research Use Note: For research use only.
General biochemistry context (no therapeutic/clinical claims)
2-(3-Chlorophenoxy)-2-methylpropanoic acid is a synthetic aromatic carboxylic acid. It is not a naturally occurring metabolite and has no intrinsic biological role in standard metabolic pathways.
The phenoxyisobutyric acid motif is widely studied in environmental chemistry and toxicology as a hydrophobic weak acid with an aromatic chromophore, useful in analytical method development and sorption/partitioning studies.
Acid-base behavior: At physiological pH, the compound would predominantly exist as its carboxylate anion (given pKa for related structures ~3.2–3.5, literature), influencing membrane interaction and protein binding in experimental systems.
Protein interactions (general): Carboxylates can form ionic pairs with basic residues (Lys/Arg) and hydrogen-bond networks; the aryl ether/chloro substituent enhances hydrophobic interactions in binding studies. Such properties are often leveraged in in vitro binding or partitioning assays.
Caution: Any biological testing should be conducted under appropriate approvals and strictly for laboratory research. No health-related performance or effects are implied or warranted for this product.
Buffer Applications
This compound is not a standard buffering agent.
Applicability
As a monocarboxylic weak acid, it can form salts with bases, but it lacks the high solubility, defined pKa spacing, and low hydrophobicity required for practical laboratory buffers.
For pH control in the acidic range, use established buffers (e.g., acetate, citrate, MES). For neutral/basic ranges, use HEPES, MOPS, TRIS, phosphate.
Practical note
In method development or extraction workflows, its acid/base form can be toggled (acid vs. carboxylate) to manipulate partitioning, but this is not “buffering” in the classical sense.
Green Alternatives
Consider greener solvents and reagents when processing this phenoxy carboxylic acid. The core molecule itself is fixed; greenness gains come from medium and reagent selection.
Solvent choices (comparative, general)
Replace DCM/chloroform with EtOAc, 2-MeTHF, CPME, or toluene where feasible.
Use MeOH/EtOH in place of more hazardous alcohols for recrystallization or esterification when compatible with selectivity.
Comparison snapshot (qualitative)
DCM: Excellent solvating power; high EHS concern, halogenated waste.
EtOAc: Biodegradable, low toxicity; similar polarity; easy removal.
2-MeTHF: Bio-based, good water immiscibility, supports many couplings; can form peroxides—monitor and manage.
CPME: Broad liquid range, low peroxide formation relative to ethers, hydrophobic—useful for extractions.
Reagent alternatives (general)
Swap SOCl2 with Ghosez reagent or mixed anhydrides to avoid corrosive off-gassing, where practical.
Favor catalytic esterification (Amberlyst-15) or enzymatic approaches for selective transformations.
For amide bond formation, consider EDCI/ethyl(HOBt) alternatives such as COMU or green coupling strategies (T3P) to reduce urea waste.
Workup/waste minimization
Utilize bicarbonate/carbonate washes for selective phase transfers instead of repeated solvent-intensive washes.
Optimize crystallizations to replace chromatographic purifications where possible (reduced silica/solvent use).
Pharmaceutical Uses
Item-specific
No pharmacopeial status or excipient role is specified for this item; refer to CoA/Spec Sheet.
General formulation/manufacturing context (no therapeutic claims)
Phenoxyisobutyric acids and derivatives may be encountered as reference standards or process/degradation markers in analytical methods. The meta-chloro isomer can serve as a positional isomeric impurity standard for related substances testing in discovery or process chemistry.
As a carboxylic acid building block, it can be converted to esters, amides, and pro-moieties during lead optimization or for preparing internal process controls.
Physicochemical profile: Moderately lipophilic weak acid—useful in studying permeability/solubility trade-offs, salt screening (Na+, K+, organic amines), and crystallization behavior of aryl-ether acids.
Regulatory caution
This catalog item is for research use only. No statements regarding safety, efficacy, or therapeutic use are made or implied.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical values for this compound class (not product specifications)
Molecular weight: ~214.65 g/mol (calculated from C10H11ClO3)
Acid dissociation: pKa of phenoxyisobutyric acids typically ~3.2–3.5 (literature); exact value for the 3-chloro isomer may vary slightly.
LogP: Expected moderately lipophilic (literature for related phenoxyisobutyric acids logP ~2.7–3.3); ionic state (as carboxylate) increases aqueous solubility.
Solubility profile (qualitative, literature):
Neutral form: sparingly soluble in water; soluble in common organic solvents (MeOH, EtOH, acetone, acetonitrile, DCM, EtOAc).
As salts (Na+, K+): markedly more water-soluble.
Melting point, boiling point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Notes for practice (general):
The compound behaves as a weak acid; solubility in water increases with pH > pKa. Partitioning is pH-dependent—important for extractions and chromatography method development.
In RP-HPLC UV detection, aromatic chromophore offers strong absorbance around 200–230 nm and a shoulder 250–280 nm (literature, qualitative). Exact ε/λmax not specified for this item.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general information)
Analytical/AR grade: Emphasizes low inorganic/organic contaminants and suitability for quantitative analysis.
Synthetic grade: Appropriate for routine synthesis where ultra-low trace impurities are not critical.
HPLC/UV grade (for solvents/standards): Low UV absorbance background and low particulate/metal content; relevant if using as an analytical standard.
Impurity considerations for phenoxy acids (general)
Potential related impurities: Positional isomers (e.g., 2- or 4-chloro), unreacted phenols/acids, ester residues, and inorganic halides.
Trace metals/UV cutoff/water content/peroxides: Not specified for this item; refer to CoA/Spec Sheet.
What to check on receipt
Verify identity by 1H/13C NMR (tertiary carboxyl signal patterns; phenoxy aromatic pattern), IR (broad O–H ~2500–3300 cm−1, C=O ~1710–1730 cm−1), and HRMS.
Confirm purity by HPLC/GC where applicable; assess positional isomer content using well-resolved chromatographic methods.
Reaction and Applications
Synthetic roles (general for this scaffold)
Carboxylic acid handle enables formation of esters (Fischer, Steglich), amides (carbodiimide/HOBt, HATU/HOAt, EDCI), acyl chlorides (SOCl2, oxalyl chloride), and anhydrides.
The aryl chloride enables cross-coupling (Buchwald–Hartwig amination, Suzuki–Miyaura, Negishi) using Pd catalysts/ligands optimized for aryl chlorides (e.g., Pd2(dba)3/XPhos, Pd-PEPPSI). Meta-chloro position resists SNAr; metal-catalyzed routes are preferred.
The phenoxy linkage transmits electron-withdrawing effects; this can subtly lower phenyl ring nucleophilicity and influence coupling conditions.
Application domains (non-clinical)
Intermediate toward phenoxyisobutyric ester derivatives (e.g., to probe physicochemical properties, environmental fate studies, or as analytical reference materials related to fibrate-class analogs).
Use in preparing amide libraries for SAR in agrochemical/discovery workflows where the phenoxyisobutyric motif is of interest.
Practical tips
Maintain anhydrous conditions for coupling/esterification to avoid competing hydrolysis. Tertiary center minimizes racemization concerns.
For acyl chloride formation, add catalytic DMF to SOCl2 for activation; quench cautiously.
During Pd-catalyzed couplings on the aryl chloride, elevated temperatures (80–110 °C) and bulky electron-rich ligands improve rates. Monitor for potential de-etherification under strong basic/nucleophilic conditions.
Acid-base workup: Convert to carboxylate with aqueous NaHCO3 for phase manipulation; re-acidify to recover the neutral acid.
Reaction Conditions
General literature guidance (not product specifications; optimize per substrate and scale):
Esterification (Steglich)
Conditions: Carboxylic acid (1.0 eq), ROH (1.5–3.0 eq), DCC (1.1 eq), DMAP (0.1 eq) in DCM or THF, 0 °C → rt, 2–18 h.
Notes: Filter DCU byproduct; for hindered alcohols, use CDI or T3P.
Amide coupling
EDCI (1.2 eq)/HOBt or HOAt with DIPEA (2.0 eq) in DMF or DCM, rt–40 °C, 2–16 h. Alternatively HATU (1.1 eq)/DIPEA in DMF, 0 °C → rt.
Notes: As a tertiary acid center, coupling is generally clean; avoid prolonged basic heating to protect the ether linkage.
Acid chloride formation
SOCl2 (3–5 eq), catalytic DMF, 0 °C → reflux (40–70 °C depending on solvent), 1–3 h. Distill excess reagent under reduced pressure; convert in situ to amide/ester.
Catalyst/ligand: Pd2(dba)3 (1–2 mol%) with XPhos or SPhos (2–4 mol%).
Base: K3PO4 or Cs2CO3 (2–3 eq). Solvent: 2-MeTHF, toluene/H2O, or dioxane/H2O. Temp: 80–110 °C, 6–18 h.
Notes: Meta-chloro requires robust ligation; monitor for ether stability.
Workup/purification
Acid/base toggling: Extract as carboxylate into aqueous NaHCO3; re-acidify (pH ~2) and back-extract with EtOAc. Add 0.1–1% AcOH in chromatography eluent to reduce tailing of the acid.
Safety and Handling
Item-specific (from Product Data)
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
Storage conditions: Store at 2–8 °C.
Shipping: Shipped on wet ice.
General safety considerations for carboxylic aryl ethers (informational; consult SDS for authoritative guidance)
Likely hazards: May cause skin/eye irritation and respiratory tract irritation if dust/aerosols are generated (based on functional group class). Avoid ingestion and prolonged exposure.
PPE: Laboratory coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation of dust or solvent vapors during handling.
Incompatibilities: Strong oxidizers; strong bases can form carboxylate salts (increased solubility); strong acids may lead to hydrolysis only under forcing conditions. Avoid prolonged exposure to strong reducing agents and reactive metals.
First aid (overview):
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; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Organic solid; combustible. Use CO2, dry chemical, or foam. Decomposition can release HCl and irritant fumes.
Always defer to the product’s SDS for definitive hazard classification and response measures.
Solvent Selection
This is a moderately lipophilic, weakly acidic aromatic compound. Solvent choice should reflect its acid-base behavior and the need for either neutral or ionized forms.
Polarity/miscibility (literature, general)
Neutral form: Good solubility in MeOH, EtOH, acetone, acetonitrile, DCM, chloroform, THF, and EtOAc; limited solubility in water.
Ionized form (as Na/K salt): Enhanced water solubility; useful for aqueous handling or partitioning into aqueous phase.
Selection guidance
Purification by recrystallization: EtOAc/hexanes, toluene/hexanes, or alcohol/water mixtures can be explored; optimize empirically.
Chromatography: Normal phase silica with gradient of hexanes/EtOAc or toluene/EtOAc works for the neutral acid; add 0.1–1% acetic or formic acid to suppress tailing of the carboxylic acid. For RP-HPLC, aqueous buffer (pH 2–3) with MeOH or ACN improves peak shape for the unionized form.
Reaction media: For esterification/coupling, use anhydrous DCM, DMF, DCM/DMF, or THF. For salt formation, employ aqueous NaHCO3/Na2CO3, then back-extract from water after acidification.
Comparison notes (general)
DCM vs EtOAc: DCM often affords faster dissolution and better phase separation; EtOAc is greener and less dense.
MeOH vs ACN: MeOH enhances solubility for acids and is protic; ACN is aprotic and often preferred for LC method development.
Storage and Reconstitution
Item-specific (from Product Data)
Storage: Store at 2–8 °C.
Shipping: Shipped on wet ice.
General guidance for this compound class
Solid handling: Keep container tightly closed in a dry, well-ventilated place. Protect from excessive heat and direct light.
Solution stability: Prepare stock solutions freshly when possible. For short-term analytical stocks, dissolve in acetonitrile, methanol, DMSO, or ethyl acetate. Store solutions at 2–8 °C for short term (days) or at −20 °C for longer term (weeks), protected from moisture.
Concentrations: Typical analytical stocks 1–10 mg/mL; filter (0.2 µm PTFE) if using for HPLC.
Freeze–thaw: Minimize cycles. If storing aliquots at −20 °C, partition into single-use volumes.
Stability notes
The aryl ether and carboxylic acid are generally robust under neutral conditions. Avoid prolonged exposure to strong acids/bases at elevated temperature to prevent hydrolysis or ether cleavage.
Water content, residual solvents, and specific stability-indicating parameters: Not specified for this item; refer to CoA/Spec Sheet.
Always consult the product label and SDS for final instructions.
Structure and Identity
Brief description: 2-(3-Chlorophenoxy)-2-methylpropanoic acid is a chlorinated phenoxyisobutyric acid scaffold featuring a tertiary carboxylic acid center ether-linked to a meta-chlorophenyl ring.
Item-specific (from Product Data)
CAS: 17413-73-9
CID: 28529
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general reference values; not product specifications)
Preferred IUPAC name (literature): 2-(3-chlorophenoxy)-2-methylpropanoic acid
Substitution pattern: The quaternary carbon (α to the carboxyl) bears two methyl groups and an O-aryl substituent (phenoxy). The aryl ring is chlorinated at the meta (3-) position relative to the ether oxygen.
Stereochemistry: None—quaternary center is achiral because substituents include two identical methyl groups.
2D structure in words: A tert-butyl-like carboxylic acid core [C(CH3)2–CO2H] with the remaining substituent being an O–(3-chlorophenyl) group attached via an ether linkage.
Synthetic Utility
Functional group leverage
Carboxylic acid (tertiary): Enables straightforward derivatization to esters, amides, acyl halides, and mixed anhydrides. The adjacent quaternary carbon prevents enolization/racemization, simplifying coupling choices.
Aryl chloride (meta): Amenable to Pd-catalyzed cross-couplings with appropriate ligand sets; SNAr is generally unfavorable at meta positions unless strongly activated.
Phenoxy ether: Typically stable under neutral and mildly basic conditions; can be cleaved only under forcing acidic nucleophilic conditions.
Steglich esterification (DCC/DMAP) to generate screening esters; T3P or CDI as greener alternatives.
Amide formation via EDCI/HOBt or HATU; use DIPEA or NMM as base in DMF/DCM.
Suzuki–Miyaura coupling on the aryl chloride to append boronic acids (use Pd/XPhos, elevated T); Buchwald–Hartwig amination to introduce anilines.
Conversion to acid chloride (SOCl2, cat. DMF) to enable Friedel–Crafts acylations is not applicable because the acyl center is tertiary; instead, use the acid chloride for nucleophilic acyl substitutions only.
Retrosynthetic value
The scaffold disconnects to 3-chlorophenol and methacrylic-acid-derived tert-carboxyl fragments via O-alkylation/acylation strategies, informing route scouting.
Target Specificity
This product is a small-molecule reagent, not a biological affinity reagent.
Item-specific
Target/antigen, epitope, clone, isotype, species reactivity: Not applicable to this item; no such data are provided in the Product Data.
For research workflows requiring target-specific binding, consult antibody/affinity reagent listings instead.
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