(4-Cyclopentylphenyl)methanol: Properties & Lab Use FAQ

(4-Cyclopentylphenyl)methanol is a benzylic alcohol building block featuring a cyclopentyl-substituted phenyl ring, valued in organic synthesis and medicinal chemistry for its lipophilic aromatic scaffold and reactive hydroxymethyl handle.

Chemical Name

(4-Cyclopentylphenyl)methanol

SKU / Catalog Number

C191497

Molecular Formula

C₁₂H₁₆O

Molecular Weight

176.25 g/mol

Functional Group

Primary benzylic alcohol (–CH₂OH)

Key Structural Feature

Para-cyclopentyl substitution on phenyl ring

What Is (4-Cyclopentylphenyl)methanol and What Is Its Structure?

(4-Cyclopentylphenyl)methanol (CAS registry; SKU C191497) is an aryl carbinol consisting of a benzene ring bearing a cyclopentyl group at the para position and a hydroxymethyl (–CH₂OH) group at the other end. The molecular formula is C₁₂H₁₆O, giving a molecular weight of approximately 176.25 g/mol. The compound belongs to the broader class of benzylic alcohols, which are characterised by an –OH group attached to a carbon directly adjacent to an aromatic ring. The cyclopentyl substituent increases the lipophilicity of the molecule relative to unsubstituted benzyl alcohol, a property exploited in medicinal chemistry when designing compounds with improved membrane permeability.

What Are the Key Physical and Chemical Properties?

As a benzylic primary alcohol, (4-Cyclopentylphenyl)methanol is expected to be a colourless to pale yellow liquid or low-melting solid at ambient temperature, with limited water solubility driven by its hydrophobic cyclopentyl ring, yet miscible with common organic solvents such as ethanol, dichloromethane, ethyl acetate, and tetrahydrofuran. The benzylic C–OH bond is more reactive than a simple aliphatic alcohol: it undergoes facile oxidation to the corresponding aldehyde (4-cyclopentylbenzaldehyde) using mild oxidants such as MnO₂ or Dess–Martin periodinane, and is readily converted to benzylic halides or mesylates for further nucleophilic substitution. The cyclopentyl ring is chemically robust under standard laboratory conditions and does not participate in typical polar reactions at the alcohol centre. Calculated log P values for analogous cyclopentylphenyl systems typically exceed 3, indicating significant lipophilicity; the precise experimental value for this compound should be verified against the supplier's certificate of analysis.

What Are the Typical Research and Synthetic Applications?

(4-Cyclopentylphenyl)methanol serves primarily as a synthetic intermediate in medicinal chemistry and pharmaceutical research. Its hydroxymethyl group provides a versatile handle for a range of transformations: (1) Oxidation to the aldehyde, which can then participate in reductive amination, Wittig olefination, or condensation reactions; (2) Esterification to produce prodrug esters or ester-linked conjugates; (3) Etherification via Mitsunobu reaction or Williamson synthesis to access aryl methyl ethers; (4) Halogenation to generate benzylic bromides or chlorides as alkylating agents. The para-cyclopentyl group is a recognised bioisostere for tert-butyl and cyclohexyl groups in drug discovery, providing metabolic stability while maintaining appropriate lipophilicity. Researchers in fragment-based drug discovery may employ this scaffold to probe hydrophobic binding pockets in target proteins.

How Should (4-Cyclopentylphenyl)methanol Be Stored and Handled Safely?

Storage: Store the compound in a tightly sealed container, away from heat, ignition sources, and direct sunlight. A cool, dry environment (typically 2–8 °C or room temperature as specified on the certificate of analysis) under an inert atmosphere is recommended for long-term stability. As with most benzylic alcohols, oxidation under prolonged air exposure may gradually produce trace aldehyde; storing under nitrogen or argon minimises this risk.

Handling: Use standard personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Operations producing vapour or aerosols should be conducted in a well-ventilated fume hood. Although detailed toxicological data specific to this compound may be limited, it should be treated as a potential irritant in accordance with general chemical hygiene practice. Consult the Aladdin Scientific Safety Data Sheet (SDS) for current hazard classifications, first-aid measures, and disposal guidance before use.

How to Order and What Specifications Are Available from Aladdin Scientific?

(4-Cyclopentylphenyl)methanol is available from Aladdin Scientific under SKU C191497. To place an order, visit the Aladdin Scientific website, search by SKU or product name, and select the required quantity. For bulk quantities, custom purity grades, or institutional pricing, contact the Aladdin Scientific sales team directly. A Certificate of Analysis (CoA) confirming purity, lot-specific data, and physicochemical constants is available upon request or downloadable from the product page. Researchers requiring high-purity material for analytical reference or GMP-adjacent work should request the relevant specification sheet and confirm suitability prior to ordering. For questions about shipping conditions, return policies, or payment options, refer to the Aladdin Scientific Help Centre or contact customer service.

Frequently asked questions

What is the molecular formula and molecular weight of (4-Cyclopentylphenyl)methanol?

The molecular formula of (4-Cyclopentylphenyl)methanol is C₁₂H₁₆O and its molecular weight is approximately 176.25 g/mol. These values reflect the benzyl alcohol core extended by a para-cyclopentyl substituent.

What solvents are suitable for dissolving (4-Cyclopentylphenyl)methanol?

Due to its lipophilic cyclopentyl group, (4-Cyclopentylphenyl)methanol dissolves readily in common organic solvents including dichloromethane, ethyl acetate, tetrahydrofuran, and ethanol. Its solubility in water is limited; aqueous co-solvent systems or DMSO may be used for biological assay formulations. Always verify solubility experimentally under your specific assay conditions.

Can (4-Cyclopentylphenyl)methanol be oxidised to the corresponding aldehyde, and if so, how?

Yes. As a primary benzylic alcohol, (4-Cyclopentylphenyl)methanol can be selectively oxidised to 4-cyclopentylbenzaldehyde using mild oxidising agents. Common laboratory methods include MnO₂ in an inert solvent, Dess–Martin periodinane (DMP) in dichloromethane, or Swern oxidation conditions. The choice of method depends on the scale, downstream application, and functional-group tolerance required.

Is (4-Cyclopentylphenyl)methanol used as a pharmaceutical intermediate or building block?

Yes. The compound is recognised as a useful building block in medicinal chemistry. The para-cyclopentyl group acts as a bioisostere for tert-butyl or cyclohexyl moieties, offering metabolic stability and tunable lipophilicity. The benzylic alcohol functionality allows diverse downstream transformations including oxidation, esterification, etherification, and halogenation, making it applicable in the synthesis of drug candidates and bioactive small molecules.

What are the recommended storage conditions for (4-Cyclopentylphenyl)methanol (C191497)?

Store (4-Cyclopentylphenyl)methanol in a tightly sealed container in a cool, dry place, away from heat and light. For extended storage, an inert atmosphere (nitrogen or argon) is advisable to prevent gradual oxidation of the benzylic alcohol to the aldehyde. Always refer to the current Aladdin Scientific Certificate of Analysis and Safety Data Sheet for lot-specific storage instructions.

How do I obtain a Certificate of Analysis or Safety Data Sheet for C191497?

Certificates of Analysis (CoA) and Safety Data Sheets (SDS) for (4-Cyclopentylphenyl)methanol (SKU C191497) are available through the Aladdin Scientific website product page. You can search by SKU C191497 and download the relevant documents. For lot-specific CoAs or additional technical support, contact Aladdin Scientific customer service directly.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. Wiley-Interscience, 1992. General reference for benzylic alcohol reactivity and oxidation methods.
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press, 2012. Reference for alcohol functional group transformations including oxidation and esterification.
3. Aladdin Scientific product page for (4-Cyclopentylphenyl)methanol, SKU C191497. https://www.aladdin-e.com (accessed 2024).

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