5-Cyclopropylpentanoic acid - ≥95% , CAS No.5266-60-4

CAS: 5266-60-4 Cat. No.: C953147 Formula: C₈H₁₄O₂ Peso molecolare: 142.200 Numero EC: 887-308-6

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: C1CC1CCCCC(=O)O
• IUPAC Name: 5-cyclopropylpentanoic acid
• InChIKey: GIQHUMQLXXRAHV-UHFFFAOYSA-N
• INCHI: 1S/C8H14O2/c9-8(10)4-2-1-3-7-5-6-7/h7H,1-6H2,(H,9,10)
• Peso molecolare: 142.200

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Carbocyclic fatty acids
• Alternative Parents: Medium-chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Carbocyclic fatty acid - Medium-chain fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as carbocyclic fatty acids. These are fatty acids containing a carbocyclic 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: 142.200 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 142.099 Da
• Monoisotopic Mass: 142.099 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 116.000
• 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/application protocols are specified for this item in the Product Data.

• General usage notes (research context)
  • For stock solutions, prepare 0.1–1.0 M in dry DMSO, DMF, MeCN, or alcohols; filter (PTFE) if particulates are present.
  • For coupling reactions, typical charge: acid (1.0 equiv), amine/alcohol (1.1–1.5 equiv), coupling reagent (1.1–1.5 equiv for EDC; 1.1–1.2 equiv for HATU), base (2–3 equiv DIPEA). Adjust based on substrate reactivity.
  • Analytical: Monitor by LC-MS (negative ESI for acid; positive ESI for amide/ester products) and by 1H/13C NMR (CDCl3, DMSO-d6, or CD3OD).

All procedures should be validated and optimized by the end user; consult primary literature and the SDS before use.

Biological Roles

This compound is a synthetic, non-natural aliphatic carboxylic acid; no endogenous biological role is established.

• General context (literature/class-based)

  • Carboxylic acids can engage in ionic interactions with proteins when deprotonated (carboxylate), influencing binding in SAR studies. The cyclopropyl group increases conformational rigidity and can modulate metabolic stability by resisting oxidative cleavage.
  • Physicochemical properties: at physiological pH, the carboxylate is largely ionized (pKa ~4.6–4.9 for aliphatic acids), which reduces passive membrane permeability unless masked as esters or amides.

• Research relevance (non-clinical)

  • Useful as a fragment to explore hydrophobic pocket occupancy in enzyme/receptor mimetics (through its amides/esters), and as a handle for prodrug strategies (e.g., esterification to modulate permeability in biochemistry assays).

• Note: All uses are for research and laboratory investigation only. No medical, diagnostic, or therapeutic applications are claimed or implied.

Buffer Applications

This compound is not typically used as a laboratory buffer component.

• Rationale

  • Although carboxylic acids can, in principle, buffer near their pKa, the low aqueous solubility of medium-chain aliphatic acids and odor/handling considerations make them unsuitable for routine buffer preparation.
  • For pH ~4.5–5.5, acetate or citrate buffers are standard, water-soluble alternatives.

• Practical guidance

  • If handling in aqueous systems is required, adjust pH with base (NaOH, NaHCO3) to form the carboxylate salt to improve solubility; this is for extraction/processing rather than true buffering.

Green Alternatives

While the compound itself is a target/building block (not a solvent), greener choices can be made in its transformations.

• Greener solvent choices (literature guidance)

  • Replace DMF/NMP with 2-MeTHF, CPME, EtOAc, MeCN, or propylene carbonate where compatible.
  • Favor alcohol media for Fischer esterification and water/MeOH biphasic systems for extractions.

• Coupling reagent considerations

  • EDC·HCl (water-compatible) or T3P (propylphosphonic anhydride) can be lower-waste alternatives to DCC/HATU; minimizes urea byproduct handling.
  • Enzymatic esterification/amidation (lipases) in green solvents or solvent-free conditions can reduce energy and waste.

• Workup/waste

  • Use bicarbonate washes selectively to deionize and recover material; avoid excessive halogenated solvents by substituting EtOAc/MTBE where possible.

• Comparison snapshot (general)

  • Traditional: DMF + HATU, CH2Cl2 workup → high efficiency, but hazardous solvent/reagent and difficult waste.
  • Greener: 2-MeTHF + EDC·HCl (or T3P), EtOAc workup → comparable yields reported in many amide formations with improved EHS profile.

• Trade-offs

  • Some greener solvents alter solubility or reaction rates; minor re-optimization (temperature, base equivalents, concentration) may be required.

Pharmaceutical Uses

• Item-specific regulatory status: Not specified for this item; not listed as a compendial excipient in the provided data.

• General, non-clinical context

  • Role in process chemistry: Serves as an intermediate for the synthesis of amide or ester derivatives during API route scouting. The cyclopropyl group is a common motif in medicinal chemistry to tune potency and metabolic stability.
  • Formulation context: The parent acid is not a typical excipient. However, derivatives (salts, esters, amides) could be explored in pre-formulation studies for structure–property relationships (permeability, solubility, stability) in research settings.

• Compliance and documentation

  • For any GMP-lean or regulated development work, request extended documentation (CoA, TSE/BSE statements, residual solvent profile) specific to the lot. Absent such data, restrict to discovery-phase, research-only applications.

• Note: No medical or therapeutic claims are made. This product is supplied strictly for research use.

Physical Properties

• Item-specific specifications

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

• Literature/computed physical data (general guidance; not item specifications)

  • Molecular formula: C8H14O2 (computed from structure)
  • Molecular weight: 142.20 g/mol (computed)
  • Acid dissociation: pKa typically ~4.6–4.9 for aliphatic monocarboxylic acids (literature, class value)
  • Phase at ambient: expected to be a low-melting solid or viscous liquid depending on exact purity/isomer content (literature expectation for C8 aliphatic acids with rings)
  • Solubility profile (qualitative, literature):
    • Water: low at neutral pH; forms soluble carboxylate salts under basic conditions.
    • Organic solvents: good solubility in polar protic/aprotic solvents (MeOH, EtOH, i-PrOH, acetone, acetonitrile, DMSO, DMF) and in moderately nonpolar media (EtOAc, THF, toluene, CH2Cl2).
  • Partitioning: logP expected in the low-to-mid 2 range for C8 aliphatic acids when unionized (literature, class behavior).
  • Volatility: low; typical of C8 carboxylic acids (literature trend).

• Not provided for this item; consult CoA/Spec Sheet if required: exact BP/MP, density, refractive index, UV cutoff, residual water/peroxide/metal content.

Quality and Grades

• Item-specific info

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvents, and impurity profile.
  • Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on grades (general)

  • Research grade carboxylic acids are typically suitable for synthetic applications, screening, and library builds. If low UV background is important (e.g., LC-UV analytics), HPLC grade reagents/solvents are preferred for workup/analysis, but the acid itself seldom has a defined “HPLC grade.”
  • For coupling chemistry (amide/ester formation), pay attention to water content and acid-value/titration; trace water can reduce coupling efficiency. If specifications are critical (metals, peroxides, residual solvents), request the batch CoA.
  • If chiral/stereochemical purity is relevant: this compound has no stereocenters; thus, enantiomeric purity is not applicable. Regiochemical purity (absence of isomeric cyclopropylalkyl acids) may matter in SAR programs—check CoA for isomer limits if needed.

• Documentation

  • For regulated workflows or QC release, obtain the lot-specific CoA and, if required, a detailed Spec Sheet outlining acceptance criteria.

Reaction and Applications

5-Cyclopropylpentanoic acid serves as a robust building block to introduce both a lipophilic linear spacer and a metabolically resilient cyclopropyl motif.

• Representative transformations (literature/general)

  • Amide coupling: Convert to amides with EDC·HCl/HOBt, HATU, T3P, or CDI; base (DIPEA/Et3N) in DMF/MeCN/2-MeTHF. Acid chloride intermediate via SOCl2 or (COCl)2 expands scope to weakly nucleophilic amines.
  • Esterification: Fischer–Speier in alcohols with catalytic H2SO4 or p-TsOH; Steglich esterification (DCC/DMAP) in CH2Cl2 for base-sensitive substrates.
  • Reduction: BH3·THF or LiAlH4 affords the corresponding primary alcohol; two-step via acid chloride then NaBH4 also possible (Rosenmund-like modifications not applicable to aliphatic acids without activation).
  • Decarboxylative couplings: Activation as redox-active ester (NHP ester) enables Ni- or Cu-catalyzed decarboxylative C(sp3)–C cross-couplings (literature trend in photocatalysis and electrosynthesis) to elaborate the cyclopropylalkyl fragment.
  • Curtius/Schmidt pathways: Formation of acyl azide (DPPA) delivers isocyanate for urea/carbamate chemistry.

• Application domains (non-clinical)

  • Medicinal chemistry/SAR: The cyclopropyl group can tune pKa, lipophilicity, and block oxidative metabolism; the C5 spacer modulates spatial reach to target pharmacophores.
  • Materials/monomers: Amide/ester derivatives introduce constrained hydrophobic segments; useful in surface modifiers and dendrons.

• Practical notes

  • Drying the acid (vacuum, mild heat) prior to coupling improves activation efficiency. Minimize adventitious water with molecular sieves when using carbodiimides.
  • Monitor by TLC/LC-MS; acids often show strong response in negative ESI.

Reaction Conditions

General literature guidance (not item-specific; optimize per substrate):

• Amide formation (EDC·HCl/HOBt or HATU)

  • Solvent: DMF, MeCN, or 2-MeTHF
  • Base: DIPEA (2–3 equiv)
  • Temperature: 0–25 °C (scale-up often 20–30 °C)
  • Time: 1–12 h
  • Notes: Pre-cool when adding HATU to minimize exotherm; monitor by LC-MS. Additives like HOAt/oxyma improve coupling and suppress racemization (not applicable here but can aid yields).

• Fischer esterification

  • Solvent/reagent: Neat alcohol (MeOH/EtOH/i-PrOH) with 1–5 mol% H2SO4 or p-TsOH
  • Temperature: Reflux of chosen alcohol (65–83 °C)
  • Time: 2–24 h; remove water (molecular sieves or Dean–Stark for higher alcohols in toluene)

• Acid chloride formation

  • Reagent: SOCl2 (2–3 equiv) or (COCl)2 with catalytic DMF
  • Solvent: CH2Cl2 or toluene, anhydrous
  • Temperature: 0 °C to reflux (1–3 h)
  • Caution: Control off-gas (HCl/SO2/CO/CO2). Use inert atmosphere.

• Reduction to alcohol (BH3·THF)

  • Solvent: THF, anhydrous
  • Temperature: 0–25 °C; then reflux if needed
  • Stoichiometry: ~1–1.5 equiv BH3 per –CO2H
  • Workup: Quench carefully with MeOH/H2O; extract with EtOAc.

• Decarboxylative couplings (NHP ester)

  • Activation: DIC + NHPI, DMAP, CH2Cl2/EtOAc
  • Coupling: Ni(II) catalyst + photoredox (Ir/Ru) in MeCN/DMF, blue LEDs, rt–40 °C
  • Notes: Radical conditions maintain cyclopropyl ring integrity; oxygen exclusion is critical.

Safety and Handling

• Item-specific hazard details

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements/Pictograms: Not specified for this item; refer to SDS.

• General safety guidance for aliphatic carboxylic acids (literature/class-based; defer to SDS for authority)

  • Hazards: May cause skin and eye irritation; inhalation of mists/vapors may irritate respiratory tract. Strong odors possible for medium-chain acids.
  • PPE: Use safety glasses or chemical splash goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid exposure to vapors or aerosols.
  • Incompatibilities: Strong bases (forms salts, heat evolution), strong oxidizers (risk of exotherm), strong reducing agents, and acid chlorination reagents unless intended (SOCl2, oxalyl chloride—generate HCl/SO2/CO byproducts). Avoid contact with reactive metals in presence of moisture (salt formation/corrosion).
  • First aid (overview):
    • Skin: Wash with soap and water; remove contaminated clothing.
    • Eyes: Rinse cautiously with water for several minutes; remove contacts if present and easy to do; seek medical attention.
    • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
  • Handling tips: Keep containers tightly closed. Avoid prolonged heating; if generating acid chlorides/anhydrides, ensure adequate scrubbing for acidic off-gases.

• Storage per Product Data: Store at room temperature. Protect from moisture and strong oxidants.

Solvent Selection

This product is a hydrophobic, monofunctional carboxylic acid. Solvent choice depends on ionization state and target transformation.

• Polarity/miscibility (general, literature)

  • Unionized acid: soluble in polar organics (MeOH, EtOH, i-PrOH, acetone, EtOAc, THF, MeCN, DMSO, DMF) and moderately in nonpolar media (toluene, CH2Cl2, MTBE) due to hydrophobic backbone.
  • Carboxylate salts: highly soluble in water/alcohols. Aqueous basic media (NaHCO3/Na2CO3) extract the acid as its carboxylate.

• Selection by use case

  • Amide coupling: DMF, NMP, or MeCN are common; greener options include 2-MeTHF or EtOAc with modern coupling systems.
  • Fischer esterification: anhydrous ROH (MeOH/EtOH/i-PrOH) with catalytic acid; Dean–Stark in toluene or xylene for higher alcohols.
  • Acid chloride formation: anhydrous CH2Cl2, toluene, or heptane with SOCl2/oxalyl chloride; catalytic DMF may be employed.
  • Reductions to alcohol: THF, Et2O, or toluene with LiAlH4; for milder systems (BH3·THF), THF is typical.

• Practical tips

  • For analytical LC, dissolve in MeOH, ACN, or DMSO; adjust pH with a small base if solubility is limited.
  • For extractions, leverage acid/base liquid–liquid partitioning: wash organics with NaHCO3 to remove acid, then re-acidify aqueous phase to recover.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Stability guidance (general for aliphatic carboxylic acids)

  • Stable under ambient laboratory conditions. Protect from strong oxidizers and prolonged exposure to heat.
  • Hygroscopicity: low-to-moderate; however, moisture can affect downstream coupling efficiency. If critical, dry under vacuum (30–40 °C) prior to use.

• Reconstitution and solution handling (research use)

  • For reaction stocks: prepare solutions in dry solvents (DMSO, DMF, MeCN, THF, EtOAc, alcohols) at 0.1–1.0 M. Use anhydrous conditions for activation/coupling chemistry.
  • Aqueous work: dissolve by first forming the sodium/potassium carboxylate with dilute base (NaHCO3/NaOH), then adjust as required.
  • Storage of solutions: For non-aqueous solutions, store under inert gas at 2–8 °C if keeping >24 h. Avoid repeated freeze–thaw; aliquot as needed.

• Disposal: Follow institutional guidelines for organic acids. Neutralize before aqueous disposal where permitted; otherwise, collect as organic waste.

Structure and Identity

Brief description: 5-Cyclopropylpentanoic acid is an aliphatic carboxylic acid bearing a terminal cyclopropyl substituent, useful as a hydrophobic building block.

• Item-specific identifiers (from Product Data)

  • SKU: C953147
  • Product Name: 5-Cyclopropylpentanoic acid
  • CAS: 5266-60-4
  • CID: 21321698
  • InChIKey: 103078 (as provided)
  • Storage Conditions: Room temperature
  • Research Use Note: For research use only

• Computed/literature identity (general reference; not item-specific specs)

  • Preferred IUPAC name (literature): 5-cyclopropylpentanoic acid
  • Molecular formula (computed): C8H14O2
  • Molecular weight (computed): 142.20 g/mol
  • SMILES (literature): O=C(O)CCCC1CC1
  • Structural features: one carboxylic acid (–CO2H), a four-methylene spacer (–CH2–)4, and a terminal cyclopropyl ring. No heteroatoms beyond the carboxyl oxygens; no stereocenters.
  • 2D description in words: a linear C5 aliphatic chain terminating at one end with a carboxylic acid and at the other with a three-membered cyclopropyl ring; the acid carbonyl is conjugated only to sigma framework (no additional unsaturation).

Synthetic Utility

Functional group and handles:

• Carboxylic acid (–CO2H): enables amidation, esterification, acylation, Curtius rearrangement to isocyanate, activation to acid chloride/anhydride, and conversion to redox-active esters for decarboxylative couplings.
• Cyclopropyl unit: a compact, conformationally constrained, and metabolically robust hydrophobe; can influence bioactive conformations and block β-oxidation-like degradations.

Strategic uses (literature/general):

• Scaffold diversification: Rapid generation of amides with diverse amines (HATU/EDC/T3P) to probe SAR while holding a constant cyclopropylalkyl vector.
• Polarity tuning: Convert to esters (Me, Et, t-Bu) to mask acidity; unveil under mild hydrolysis to regenerate the acid.
• Cross-coupling via decarboxylation: N-hydroxyphthalimide (NHP) ester formation, followed by Ni/photoredox catalysis, installs new C–C bonds at the methylene terminus, preserving the cyclopropyl.
• Late-stage elaboration: Acid chloride route to ketones via reaction with organocuprates (acylation then reduction control) or to Weinreb amides for selective one-carbonyl additions.

Practical considerations:

• Pre-dry prior to coupling; trace water diminishes activation efficiency.
• Employ bases like DIPEA to neutralize HCl when forming acid chlorides in situ.
• Monitor for potential ring-opening under strongly acidic, high-temperature conditions; cyclopropane is generally stable under standard coupling/esterification conditions.

Target Specificity

Not applicable. This product is a small-molecule carboxylic acid, not a biological targeting reagent (e.g., antibody, probe, or ligand with defined target specificity). No target specificity information is provided in the Product Data.