3-Cyclopentylbenzaldehyde - ≥95% , CAS No.201851-05-0

CAS: 201851-05-0 Cat. No.: C970383 Fórmula: C₁₂H₁₄O Peso molecular: 174.240 Número EC: 837-555-0

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥95%

Nombres e identificadores

Sonrisas canónicas

C1CCC(C1)C2=CC=CC(=C2)C=O

IUPAC Name

3-cyclopentylbenzaldehyde

InChIKey

RXDIRVUNKJIMCU-UHFFFAOYSA-N

INCHI

1S/C12H14O/c13-9-10-4-3-7-12(8-10)11-5-1-2-6-11/h3-4,7-9,11H,1-2,5-6H2

Peso molecular

174.240

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Benzoyl derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Benzoyl derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoyl derivatives
• Alternative Parents: Benzaldehydes Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoyl - Benzaldehyde - Aryl-aldehyde - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aldehyde - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
• 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

Propiedades químicas y físicas

• Peso molecular: 174.240 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 174.104 Da
• Monoisotopic Mass: 174.104 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 170.000
• 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

Not applicable as standardized bioassay protocols (e.g., WB, IHC, IF, FC) do not pertain to a neat small-molecule aldehyde.

• For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for general literature protocols and optimization tips.

Biological Roles

This product is intended for research and synthetic use; no biological role is assigned for the neat compound.

General/contextual information (literature)

• Aromatic aldehydes can act as reactive carbonyl species with biomolecules (e.g., forming Schiff bases with amines), but such reactivity is nonspecific and typically undesirable in biological systems.
• In chemical biology or medicinal chemistry, aryl aldehydes like 3-cyclopentylbenzaldehyde may serve as intermediates en route to target molecules (e.g., benzylic alcohols, amines, or alkenes) used for probe or lead synthesis. The cyclopentyl group can modulate hydrophobicity and metabolic stability of derivatives.

No clinical or therapeutic claims are made; for laboratory research use only.

Buffer Applications

Not typically applicable. 3-Cyclopentylbenzaldehyde is a hydrophobic organic building block rather than a buffering agent.

• If used in biochemical assays, it would generally be dissolved in a co-solvent (e.g., DMSO, MeCN, ethanol) and then diluted into an aqueous buffer; maintain final organic content low (commonly ≤1–2% v/v) to avoid perturbing biological systems.
• No standard buffer systems are associated with this compound. Refer to assay-specific protocols for solvent tolerance and vehicle controls.

Green Alternatives

Greener choices relate primarily to solvent selection and reagent economy; the substrate itself is a neutral building block. Consider the following (literature/general guidance):

• Prefer greener solvents when feasible

  • Replace DCM with EtOAc, toluene, or cyclopentyl methyl ether (CPME) for condensations/olefinations where polarity needs are moderate.
  • Use 2-MeTHF in place of THF for organometallic additions; it is biorenewable, has higher boiling point, and eases phase separation.
  • Use ethanol or isopropanol for reductive aminations (with transfer hydrogenation) to minimize halogenated waste.

• Energy and waste minimization

  • Employ Dean–Stark azeotropy (toluene) or molecular sieves to drive imine/condensation chemistry, reducing excess reagents.
  • Choose catalytic methods (e.g., organocatalyzed Knoevenagel, TEMPO-catalyzed oxidations with bleach) over stoichiometric chromates.

• Comparative summary (general)

  • THF vs 2-MeTHF: similar reactivity profile for many nucleophilic additions; 2-MeTHF offers greener sourcing and easier workups but can alter selectivity in some cases.
  • DCM vs EtOAc: EtOAc is less toxic and from greener feedstocks; however, DCM’s higher polarity can accelerate some reactions—evaluate kinetics.

Note: These are general green chemistry considerations; verify compatibility with your specific transformation and required selectivity.

Pharmaceutical Uses

No pharmacopeial/excipient status is specified for this item; refer to CoA/Spec Sheet.

General manufacturing/research context (non-clinical)

• 3-Cyclopentylbenzaldehyde can function as an intermediate in multi-step syntheses toward APIs or advanced intermediates, enabling introduction of a benzylic alcohol/amine (via reduction or reductive amination) or installation of alkenes (via Wittig/HWE) at a late stage.
• The cyclopentyl group is a common lipophilicity and steric modulator in lead optimization; this aldehyde provides a convergent point for fragment assembly.
• In process development, control of aldehyde oxidation to the corresponding acid and imine formation with amine-containing excipients/reactants is essential; inline assays (GC/HPLC) are recommended.

Physical Properties

Item-specific values

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

Literature/general reference values (for planning only; not item specifications)

• Physical state: typically a colorless to pale yellow liquid for many m-substituted aryl aldehydes (literature, class behavior).
• Solubility: sparingly soluble in water; soluble in common organic solvents (e.g., DCM, Et2O, THF, toluene, acetonitrile, alcohols) (literature, general for aryl aldehydes).
• Acid/base behavior: non-basic; undergoes hydration/imine formation with nucleophiles; no relevant pKa for a simple aldehyde (literature).
• LogP: expected moderately hydrophobic due to aryl + cycloalkyl (qualitative, literature rationale).
• Refractive index, density, BP/MP, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Notes for practitioners

• The aldehyde can slowly oxidize to the corresponding benzoic acid derivative upon prolonged air exposure; minimize headspace oxygen during storage/handling.
• Vapor pressure expected to be low-to-moderate for an aryl aldehyde of this MW; handle in a fume hood regardless.

Quality and Grades

Item-specific quality information

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

General guidance on grades for aldehydes/building blocks

• Research grade: Suitable for most synthetic applications; may contain trace oxidation products (acids) or alcohols. If sensitive reactions are planned (e.g., organometallic additions), pre-purify or verify by GC/HPLC.
• High-purity/GC/HPLC grade: Tighter limits on non-volatile residue and UV-absorbing impurities; beneficial for photochemical studies or analytical calibration.
• Water content: Not specified for this item; check CoA if Karl Fischer water limits are critical (e.g., for Grignard chemistry).
• Peroxide/acid content: Aldehydes do not form peroxides like ethers, but they can oxidize to acids. If acid-sensitive chemistry is planned, assay/neutralize trace acid or freshly distill.

Best practices to assure quality-in-use

• Verify identity and purity by 1H/13C NMR and GC or HPLC prior to scale-up.
• If necessary, purify by vacuum distillation or flash chromatography on silica (hexanes/EtOAc or toluene gradients). Avoid prolonged exposure to basic alumina (can promote side reactions).
• Store under inert gas with an oxygen/moisture barrier to minimize oxidation/hydrate formation.

Reaction and Applications

3-Cyclopentylbenzaldehyde is a versatile electrophilic building block. Common synthetic applications (literature/general) include:

• Nucleophilic additions

  • Grignard and organolithium reagents add to the aldehyde to give secondary benzylic alcohols after workup. The cyclopentyl substituent increases lipophilicity of products, useful in medicinal chemistry SAR.
  • Cyanation (NaCN, TMSCN with Lewis acid) affords cyanohydrins as masked carbonyl derivatives.

• Condensation chemistry

  • Imine/oxime/hydrazone formation with amines, hydroxylamine, and hydrazines; reductive amination gives benzylic amines.
  • Wittig/Horner–Wadsworth–Emmons/Knoevenagel reactions provide styrenyl or substituted alkene products; E/Z control depends on reagent set and conditions.

• Redox transformations

  • Reduction to the corresponding benzyl alcohol (NaBH4 typically too mild; use NaBH(OAc)3 for imines or catalytic hydrogenation/diisobutylaluminum hydride/Luche conditions for aldehyde directly).
  • Oxidation to the benzoic acid derivative via e.g., Jones, TEMPO/bleach, or Pinnick oxidation.

• Electrophilic aromatic substitution (EAS) on the ring

  • The aldehyde is strongly deactivating and meta-directing; the cyclopentyl group is weakly activating/ortho,para-directing. Overall, substitution patterns are governed primarily by the aldehyde’s meta-directing influence under typical EAS conditions.

Practical tips

• Use dry, oxygen-limited conditions for water- or air-sensitive steps; aldehydes can oxidize or polymerize under harsh conditions.
• For imine formation, include 3 Å molecular sieves or employ Dean–Stark in toluene to drive equilibrium.
• For base-catalyzed condensations, monitor to avoid over-condensation or self-aldol of partners with enolizable carbonyls.

Reaction Conditions

The following are general literature-based conditions for aryl aldehydes and should be optimized for 3-cyclopentylbenzaldehyde; they are guidance, not specifications.

• Grignard addition to form secondary alcohols

  • Typical: RMgX (1.1–1.5 equiv) in dry THF or 2-MeTHF, 0 °C to rt, 0.5–4 h; aqueous NH4Cl quench. Many substrates give 70–95% yields depending on sterics/electronics.

• Reductive amination to benzylic amines

  • Aldehyde + amine (1.0–1.5 equiv) in MeOH/EtOH or toluene with 3 Å sieves; NaBH3CN (1.2–2.0 equiv) or NaBH(OAc)3, rt to 50 °C, 2–18 h. Hydrogenation (H2, Pd/C) in EtOH also common.

• Wittig/HWE olefination

  • Ylide/phosphonate (1.2–2.0 equiv) in THF or DCM, −78 °C to rt; E/Z ratio controlled by reagent (stabilized favors E). Typical isolated yields 60–90%.

• Oxidation to acid

  • Pinnick: NaClO2 (1.5–2.0 equiv), NaH2PO4 buffer (pH ~6), co-oxidant (2-methyl-2-butene), MeCN/H2O, 0–25 °C, 1–4 h.
  • TEMPO/bleach: TEMPO (1–5 mol%), NaOCl (1.5 equiv), KBr (cat.), pH ~9, 0–25 °C.

• Formation of oximes/hydrazones

  • Hydroxylamine·HCl (1.1–1.5 equiv), pyridine/EtOH or MeOH, rt to reflux, 1–6 h; dehydration to nitriles requires separate conditions.

• Safety/handling during reactions

  • Maintain inert atmosphere for moisture/air-sensitive steps; aldehydes can oxidize or participate in undesired condensations under basic conditions.

Reported conditions are representative for aryl aldehydes broadly; confirm on small scale for this specific substrate.

Safety and Handling

Item-specific hazard data

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

General safety guidance for aromatic aldehydes (literature/general)

• Hazards: May cause skin/eye irritation and respiratory irritation; sensitization is possible for aldehydes. Avoid inhalation and contact.
• PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. Employ fume hood.
• Incompatibilities: Strong oxidizers (risk of rapid oxidation), strong bases/nucleophiles (can trigger aldol/condensation or Cannizzaro-type pathways in non-enolizable aldehydes; this substrate is enolizable via aryl ring only, but base still promotes side reactions), strong acids (may catalyze polymerization/acetals), reducing agents (can reduce to alcohol), and reactive amines (imine formation).
• Stability considerations: Aldehydes can autoxidize to acids under air/light; consider storing under inert atmosphere and keeping containers tightly closed.
• First aid (summary; defer to SDS): Rinse eyes/skin with water for ≥15 min upon contact; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Combustible organic liquid; use CO2, dry chemical, or foam. Vapors may be irritating; avoid ignition sources.

Always consult the product’s SDS for authoritative, current safety information.

Solvent Selection

Applicability: As a moderately hydrophobic aryl aldehyde, 3-cyclopentylbenzaldehyde is soluble in many organic solvents; choose solvent based on reaction class and workup constraints.

• Polarity/miscibility (general)

  • Expected to dissolve well in nonpolar to moderately polar organics: toluene, DCM, chloroform, THF, EtOAc, MeCN, alcohols.
  • Poorly soluble in water; biphasic systems (e.g., toluene/H2O with phase-transfer or base) are common for condensations (e.g., Knoevenagel, aldol with other partners).

• Typical choices by application

  • Nucleophilic additions (Grignard/organolithium): dry THF, 2-MeTHF, or toluene/ether mixtures under inert atmosphere.
  • Imine formation/reductive amination: toluene, MeOH/EtOH, MeCN; use molecular sieves or azeotropic removal of water.
  • Wittig/HWE olefinations: THF, DCM, toluene; temperature control from −78 to room temperature depending on ylide/stabilization.
  • Oxidation/reduction: DCM or MeCN for mild oxidations; alcohols or THF for catalytic hydrogenation/reductions.

• Comparison notes (general)

  • DCM vs toluene: DCM offers faster kinetics for many condensations; toluene facilitates Dean–Stark water removal and higher temperature operation.
  • THF vs 2-MeTHF: 2-MeTHF is greener and less miscible with water, aiding separations; THF often offers broader literature support.

These are literature-based, general considerations; optimize solvent choice empirically for your transformation.

Storage and Reconstitution

Item-specific storage

• Storage Conditions: Room temperature (as provided in Product Data).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General handling guidance for aldehydes

• Keep container tightly closed in a dry, well-ventilated place. Minimize exposure to air and light to reduce slow oxidation to the corresponding acid.
• For long-term storage, consider an inert gas blanket (N2 or Ar) and use amber glass if available.
• If solidification occurs on cooling (some aryl aldehydes can supercool), warm gently to room temperature and mix to ensure homogeneity before dispensing.
• Reconstitution: Not applicable; supplied neat. If preparing stock solutions for screening, use dry solvents (e.g., DMSO, MeCN, toluene, THF, EtOH) and store aliquots sealed under inert atmosphere at low temperature as needed.

Always consult the product label and CoA/SDS for any item-specific instructions beyond the general guidance above.

Structure and Identity

Brief description: 3-Cyclopentylbenzaldehyde is an aromatic aldehyde bearing a cyclopentyl substituent meta to the formyl group on a benzene ring.

• Item-specific identifiers (from Product Data)

  • SKU: C970383
  • Product Name: 3-Cyclopentylbenzaldehyde
  • CAS: 201851-05-0
  • InChIKey: 328400 (as provided)
  • Category Path: 全部 / 可售 / 生命科学

• Computed/literature identifiers (for reference; not item specifications)

  • Molecular formula (literature/computed): C12H14O
  • Molecular weight (literature/computed): ~174.24 g/mol
  • SMILES (literature): O=Cc1cccc(c1)C2CCCC2

• Structural features (general chemistry description)

  • Functional groups: one aryl aldehyde (–CHO) on a benzene ring; one cycloalkyl (cyclopentyl) substituent.
  • Ring systems: one benzene ring (aromatic, planar) and one cyclopentane ring (alicyclic, non-aromatic).
  • Substitution pattern: the cyclopentyl is at the 3-position (meta) relative to the aldehyde.
  • Stereochemistry: none (no stereocenters); conformational flexibility arises from the cyclopentyl ring and aryl–alkyl C–C bond.
  • 2D description: a benzene ring bearing a formyl group at C1 and, at C3 (meta), a saturated five-membered ring attached via a benzylic sp3 carbon.

Synthetic Utility

Functional handles and reactivity (literature/general)

• Aldehyde carbonyl: electrophile for nucleophilic additions (RMgX/RLi, cyanation), condensations (imines/oximes/hydrazones, Knoevenagel), and olefination (Wittig/HWE). Can be reduced to alcohols or oxidized to acids.
• Aromatic core: supports further substitution under SEAr with the strong meta-directing influence of –CHO; the cyclopentyl group provides steric bulk and weak electron donation (hyperconjugation), potentially biasing regioselectivity under specific conditions.

Retrosynthetic value

• Serves as a branch point to diverse chemotypes: benzylic amines (reductive amination), secondary alcohols (organometallic addition), alkenes (olefination), and carboxylic acids/esters (oxidation/derivatization).
• Cyclopentyl-bearing frameworks are prevalent in agrochemical and medicinal scaffolds; this aldehyde enables late-stage diversification without pre-activation of the ring.

Practical tips

• For clean nucleophilic additions, rigorously dry solvents and glassware; quench at low temperature to control exotherm.
• For imine formation on hindered amines, use azeotropic water removal (Dean–Stark in toluene) or 3 Å sieves; catalytic acid (0.1 equiv p-TsOH) can accelerate but watch for acetalization/polymerization.
• Monitor for over-oxidation or self-condensation by GC; include antioxidants or store under inert gas to suppress aging.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent or antibody.

• No antigen/epitope, species reactivity, clone, or isotype information applies.