5-(3-Chlorophenoxy)pentanoic acid - ≥95% , CAS No.7170-52-7

CAS: 7170-52-7 Cat. No.: C989105 Formula: C₁₁H₁₃ClO₃ Peso molecolare: 228.670

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1=CC(=CC(=C1)Cl)OCCCCC(=O)O

IUPAC Name

5-(3-chlorophenoxy)pentanoic acid

InChIKey

GHDJNPDNWTXTND-UHFFFAOYSA-N

INCHI

1S/C11H13ClO3/c12-9-4-3-5-10(8-9)15-7-2-1-6-11(13)14/h3-5,8H,1-2,6-7H2,(H,13,14)

Peso molecolare

228.670

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Chlorobenzenes Alkyl aryl ethers Aryl chlorides Monocarboxylic acids and derivatives Carboxylic acids Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Phenol ether - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Monocyclic benzene moiety - Aryl halide - Monocarboxylic acid or derivatives - Ether - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organochloride - Organohalogen compound - Carbonyl group - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 228.670 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 228.055 Da
• Monoisotopic Mass: 228.055 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 196.000
• 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-specific, vendor-validated protocols are provided for this small-molecule reagent.

General handling suggestions:

• Prepare concentrated stocks in anhydrous DMSO or DMF; filter through 0.2 µm PTFE if needed.
• For aqueous assays, pre-neutralize with equimolar NaOH/KOH to form the carboxylate salt, then dilute into buffered media.
• For chromatographic analysis, add 0.1% formic or acetic acid to organic eluents to minimize tailing of the free acid.

For detailed, application-specific procedures, consult primary literature relevant to your transformation or assay system.

Biological Roles

Item-specific biological activity data are not provided for this SKU. This compound is a synthetic small molecule with no established endogenous role.

General context for the scaffold (no clinical claims):

• Phenoxyalkanoic acids are a well-known chemotype in chemical biology and agrochemical structure–activity studies, often explored as analogs in receptor-binding, transport, and partitioning investigations due to their amphiphilic nature (aryl lipophilicity plus an ionizable carboxylate).
• At physiological pH, the carboxyl group is largely deprotonated, favoring interactions and transport behaviors characteristic of monocarboxylates.
• The 3-chloro substituent modulates electronic properties and lipophilicity of the aryl ring, influencing membrane association and protein binding in exploratory assays.

Use restrictions: For research use only. Any biological testing should be conducted under appropriate approvals and safety oversight. No medical, diagnostic, or therapeutic use is implied.

Buffer Applications

This product is not a conventional buffering agent. As a monoprotic carboxylic acid, it lacks a high-capacity, narrow pH buffering window compared to dedicated buffers (e.g., acetate, phosphate, Tris).

• Practical notes:
  • The free acid can be deprotonated to its sodium/potassium salt for enhanced aqueous solubility in assays, but this serves solubilization rather than buffering.
  • If a buffer near pH ~4–5 is needed, consider standard systems such as acetate or citrate; for near-neutral pH, use phosphate or HEPES.

Focus on the Solvent Selection section for handling and stock preparation guidance.

Green Alternatives

Sustainability considerations focus on solvent and reagent choices used with this substrate, as the molecule itself is a stable organic acid/ether.

• Prefer greener solvents when feasible:

  • Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME), or toluene for extractions and reactions when solubility allows.
  • For polar media, consider acetonitrile or acetone instead of DMF/NMP; for stock solutions, DMSO remains common but minimize volumes.

• Greener coupling strategies:

  • Use water-compatible carbodiimide systems (EDC·HCl with N-hydroxysuccinimide) in mixed aqueous-organic media to reduce chlorinated waste.
  • Explore enzymatic esterifications in solvent-free or ionic liquid systems for selective transformations of the carboxyl group.

• Energy and process intensity:

  • Cross-couplings of aryl chlorides can proceed under microwave or flow conditions, shortening reaction times and potentially lowering energy usage.

• Waste/reagent comparison (general):

  • Traditional: DCM workups, DMF reactions, SOCl2 for acid chlorides (releases SO2/HCl).
  • Alternative: EtOAc or 2-MeTHF workups; MeCN/MeTHF as reaction media; T3P (propylphosphonic anhydride) as a lower-toxicity coupling reagent with benign byproducts.

Balance green substitutions against performance; verify purity profiles and yields as greener media can affect solubility and reaction rates.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item.

General context (no therapeutic claims):

• In medicinal chemistry workflows, aryl–alkyl ether carboxylic acids like this are frequently used as intermediates for amide and ester libraries to probe SAR around aryl chloride handles (which can be diversified via cross-coupling).
• The free acid functionality facilitates salt screening and physicochemical optimization (e.g., logD modulation via esterification or salt formation) during lead development.
• If formulation studies are pursued, conventional practices apply (e.g., formation of sodium/potassium salts to increase aqueous solubility); however, no formulation guidance is provided for this specific product.

For regulated applications, obtain comprehensive characterization and impurity profiling from the lot-specific CoA and follow applicable guidelines. This catalog item is supplied strictly for research use only.

Physical Properties

Item-specific physicochemical specifications (e.g., exact melting/boiling point, density, refractive index, UV cutoff) are not provided for this catalog entry. Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for the chemotype (for planning only; not product specifications):

• Phase/appearance: Aromatic ether–carboxylic acids of comparable size are often low-melting solids or viscous oils; exact form for this SKU is not specified.
• Acid–base: Monoprotic carboxylic acid; expected pKa in water ~4–5 (literature, typical for aliphatic carboxylic acids adjacent to ether/aryl groups).
• Solubility profile (qualitative):
  • Organic: Good solubility anticipated in polar aprotic solvents (DMSO, DMF, acetone), chlorinated solvents (DCM, chloroform), and moderately in ethyl acetate and alcohols.
  • Aqueous: Low at neutral pH; markedly increased solubility in basic aqueous media as the carboxylate salt.
• Partitioning: Presence of aryl ring and ether suggests moderate lipophilicity; no item-specific logP available.
• Thermal behavior: Carboxylic acids may show broad melting behavior if impure or if liquid; avoid overheating to prevent decarboxylation/ether cleavage under harsh conditions.

Always consult the product’s CoA/SDS for authoritative physical constants. Use small trial dissolutions to confirm solvent choice before scale-up.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvent limits, and related substance profile.

Guidance for interpreting common grades (general information):

• Research grade: Suitable for synthesis, screening, and method development. Impurity profile supports general laboratory use.
• Analytical or HPLC grade (if stated on CoA): Implies tighter controls on UV-absorbing impurities and residue levels, beneficial for trace analysis or detector baselines.
• Stabilizers/inhibitors: None stated for this SKU. If present in a specific lot, the CoA will note the identity and level; consider this in downstream reactions (e.g., acid-catalyzed steps or hydrogenations).

Quality considerations specific to this chemotype:

• Carboxylic acid titer and water content can influence coupling efficiencies; if critical, verify by potentiometric titration or Karl Fischer before scale-up (item-specific limits not provided here).
• Trace phenolic or hydrolytic byproducts (e.g., 3-chlorophenol) can arise from ether cleavage under harsh storage; routine NMR/UPLC checks are recommended for sensitive applications.

Documentation: Request the lot-specific CoA/SDS for assay, residual solvents, and any compendial tests applicable to your application.

Reaction and Applications

This molecule serves as a versatile bifunctional building block: an aryl chloride (on the ring), an ether linkage, and a terminal carboxylic acid enable orthogonal transformations.

• Carboxylate chemistry:
  • Esterification (Fischer, Steglich) to access lipophilic esters for prodrug or materials studies.
  • Amide formation via carbodiimide (EDC/DMAP, DCC), uronium coupling (HATU, HBTU), or acid chloride routes (SOCl2 or oxalyl chloride activation) for SAR libraries.
• Aryl chloride cross-couplings (literature guidance):
  • Suzuki–Miyaura: Pd catalysts with dialkylbiaryl phosphines (e.g., SPhos, XPhos); bases such as K3PO4 or Cs2CO3; 60–110 °C in toluene/dioxane/MeCN/THF.
  • Buchwald–Hartwig amination: BrettPhos/XPhos ligands, NaOtBu or KOtBu, 80–110 °C; tolerate carboxylate as free acid or protected ester depending on base strength.
  • Carbonylative couplings using CO (Pd) to elaborate the aryl position.
• Directed metalation/functionalization:
  • The phenoxy substituent is an ortho/para director; directed ortho metalation adjacent to O– may be achievable under strong base (s-BuLi/TMEDA) on suitably protected derivatives.
• Ether stability and cleavage:
  • Aryl–alkyl ethers resist many conditions but can be cleaved under strong Lewis/Brønsted acids (e.g., BBr3, HBr) to regenerate 3-chlorophenol and a ω-hydroxypentanoic acid.
• Applications (typical for this scaffold):
  • Intermediate for synthesizing phenoxyalkanoate derivatives used in agrochemical SAR, receptor-binding probes, and polymer/ester materials. No medical/therapeutic claims are made.

Drying the free acid and controlling base strength improve coupling yields; protect the acid (as ester) when strongly basic cross-couplings are required.

Reaction Conditions

General literature guidance for typical transformations of this scaffold (not product specifications):

• Esterification (Fischer): Alcohol (3–10 eq), catalytic H2SO4 or p-TsOH, Dean–Stark in toluene or refluxing alcohol; 60–120 °C, 2–16 h. For acid-sensitive contexts, use DCC/DMAP or Steglich (DCC, DMAP, CH2Cl2, 0–25 °C).
• Amide coupling:
  • EDC·HCl (1.1–1.5 eq), HOBt or Oxyma (1.1–1.5 eq), base (DIPEA, 2–3 eq) in DMF/MeCN, 0–25 °C to rt, 1–12 h.
  • HATU (1.1–1.3 eq), DIPEA (2–3 eq), DMF/DMF–DCM, 0–25 °C, 0.5–4 h; monitor for O-acylurea suppression.
  • Acid chloride route: SOCl2 (2–4 eq), catalytic DMF, reflux 0.5–2 h, then couple in DCM with amine/base at 0–25 °C.
• Cross-coupling on aryl chloride (representative):
  • Suzuki–Miyaura: Pd2(dba)3 (1–2 mol%) + SPhos/XPhos (2–4 mol%), boronic acid (1.2–1.5 eq), base (K3PO4, Cs2CO3 2–3 eq), 80–105 °C in dioxane/H2O or toluene/EtOH/H2O, 2–12 h.
  • Buchwald–Hartwig amination: Pd(OAc)2 (1–3 mol%) + BrettPhos/RuPhos (2–6 mol%), amine (1.2–1.5 eq), NaOtBu or KOtBu (2–3 eq), 80–110 °C in toluene/dioxane, 2–16 h. Consider protecting or neutralizing the acid to avoid base consumption.
• Ether cleavage (if desired): BBr3 (1–3 eq) in DCM at −78 to 0 °C, then warm to rt; or reflux HBr/AcOH (conditions may affect aryl chloride).

Always optimize on small scale; the free acid can attenuate bases/catalysts—use esters or in situ neutralization to improve conversions.

Safety and Handling

• GHS classification, signal word, and hazard statements: Not specified for this item; refer to SDS for authoritative information.
• Anticipated hazards (general, not product-specific): Carboxylic acids can be irritants to skin/eyes; aryl chlorides/ethers may cause respiratory irritation if aerosolized. Avoid ingestion, inhalation of dust/mist, or skin contact.
• Personal protective equipment (PPE): Laboratory coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to control vapors/aerosols.
• Incompatibilities: Strong oxidizers; strong bases generate the corresponding carboxylate salt (exotherm possible upon neutralization). Prolonged exposure to strong acids/bases can promote ether cleavage. Avoid reactive acylation agents unless intentionally used under controlled conditions.
• Handling tips:
  • Prevent moisture ingress if you require the free acid (base will form salts).
  • When weighing potentially low-melting solids or viscous oils, pre-cool or use tared containers to minimize loss.
• First aid (general):
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor for respiratory irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Combustible organic compound; use CO2, dry chemical, or foam. Thermal decomposition can release corrosive/irritant fumes (e.g., HCl, COx). Store away from ignition sources.

Always defer to the SDS provided for this SKU for definitive hazard and response guidance.

Solvent Selection

Chemotype-driven guidance for 5-(3-chlorophenoxy)pentanoic acid (aryl–alkyl ether with a terminal carboxylic acid):

• Polarity/miscibility (qualitative):
  • Readily soluble in DMSO, DMF, NMP, acetone, acetonitrile, chloroform, and dichloromethane; moderately soluble in ethyl acetate and alcohols (MeOH/EtOH).
  • Poorly soluble in water at neutral pH; converts to a water-soluble carboxylate in basic media (e.g., pH > 7.5 with NaHCO3/Na2CO3).
• Stock solutions for screening/biology:
  • Prepare concentrated stocks in anhydrous DMSO (e.g., 10–100 mM) and dilute into assay buffers with final DMSO ≤1–2% v/v to minimize solvent effects.
• Purification solvents:
  • Normal-phase chromatography: Hexanes/EtOAc or toluene/EtOAc gradients exploit the compound’s intermediate polarity; addition of 0.1–1% acetic acid can suppress tailing of the free acid.
  • Reverse-phase: MeCN/H2O with 0.1% formic acid or ammonium bicarbonate when analyzing as the carboxylate.
• Reaction media:
  • Couplings/activations: DCM, THF, MeCN, or DMF are typical; ensure base selection accounts for acid–base equilibria.
• Comparison notes (general):
  • DMSO/DMF maximize solubility but can complicate workup; EtOAc/MeTHF offer greener extractions with reasonable solubility.

Always confirm actual solubility with a small trial, as crystallinity and polymorphs can shift behavior.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place away from heat and incompatible materials.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution and solution handling (general guidance):

• Solubility: Readily dissolved in DMSO, DMF, acetone, or chlorinated solvents; moderate in EtOAc/alcohols; low in water unless basified.
• Stock solutions: Prepare at 10–100 mM in dry DMSO or DMF. For aqueous systems, neutralize to the sodium/potassium salt with equimolar base before dilution. Filter sterilize if sterility is required (0.2 µm PTFE).
• Stability: Store solutions at 2–8 °C for short term; for longer-term storage, aliquot and freeze (−20 °C) to minimize hydrolysis or oxidation. Avoid repeated freeze–thaw cycles.
• Container compatibility: Use glass or high-quality polypropylene; avoid reactive metals in basic solutions due to potential corrosion/salt formation.

Always consult the lot-specific CoA/SDS for definitive storage constraints and solution stability data.

Structure and Identity

5-(3-Chlorophenoxy)pentanoic acid is an aryl–alkyl ether bearing a terminal carboxylic acid. The molecule comprises a 3-chlorophenyl ring connected via a phenoxy oxygen to the ω-position of a pentanoic acid chain.

• Item-specific identifiers (from Product Data):

  • CAS: 7170-52-7
  • InChIKey: 101963 (as provided)
  • SKU: C989105

• Research use: For research use only

• Structural features (general description):

  • Functional groups: carboxylic acid (–CO2H) and aryl–alkyl ether (Ar–O–alkyl); aryl ring carries a meta-chloro substituent.
  • Connectivity (verbal 2D description): HOOC–CH2–CH2–CH2–CH2–CH2–O–C6H4(Cl-3). The ether oxygen links C5 of the pentanoic acid chain to the phenyl ring; chlorine resides at the ring’s 3-position relative to the ether oxygen.
  • Stereochemistry: None (achiral, no stereocenters).

• Computed/literature identifiers and composition (literature/computed; not item-specific):

  • Molecular formula (computed): C11H13ClO3
  • Molecular weight (computed): ~228.68 g/mol
  • Representative SMILES (literature): O=C(O)CCCCOc1cccc(Cl)c1

• Category context: Listed under 生命科学 (Life Sciences); commonly used as a synthetic intermediate and reference compound in chemical biology and agro/auxin-mimetic structure–activity studies (no clinical use implied).

Synthetic Utility

5-(3-Chlorophenoxy)pentanoic acid offers orthogonal handles enabling modular synthesis:

• Carboxyl group transformations:
  • Esterification (Fischer, Steglich) to tune lipophilicity or serve as protecting groups.
  • Amide couplings (EDC/HOBt, HATU, T3P) to introduce diverse amines; mixed anhydrides or acid chlorides enable hindered couplings.
  • Decarboxylative variants (photoredox, silver-mediated) can forge C–C bonds from activated carboxylates (literature trend).
• Aryl chloride diversification:
  • Pd-catalyzed Suzuki, Negishi, Kumada, or Buchwald–Hartwig couplings broaden aryl substitution; modern ligands enable activation of aryl chlorides under relatively mild conditions.
• Ether linkage as a scaffold element:
  • The phenoxy ether confers rigidity and electronics akin to anisole analogs, biasing para/ortho reactivity. Under forcing Lewis/Brønsted acid, selective cleavage can unmask the phenol and a terminal alcohol, enabling branch-point elaboration.
• Retrosynthetic flexibility:
  • Disconnection to 3-chlorophenol and a 5-halo- or 5-tosyl-pentanoic acid derivative allows convergent assembly via Williamson ether synthesis (base: K2CO3/DMF; phase-transfer variants for scale).

These features make the compound suitable as a hub for library generation, linker design, and materials motifs where both an aromatic platform and an ionizable terminus are desired.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological macromolecule or affinity reagent. No antigen, epitope, or isotype information is associated with this item.