4-Chloro-α-methylbenzyl Alcohol: Properties & Lab Use FAQ

4-Chloro-α-methylbenzyl Alcohol is a halogenated chiral benzylic alcohol widely used as a synthetic intermediate in pharmaceutical and fine-chemical research.

IUPAC Name

1-(4-Chlorophenyl)ethanol

Molecular Formula

C₈H₉ClO

Molecular Weight

156.61 g/mol

SKU

C153305

Functional Groups

Secondary benzylic alcohol with aromatic chloro substituent

Chiral Center

One stereocenter at the α-carbon; available as racemate or enantioenriched form

What Is 4-Chloro-α-methylbenzyl Alcohol?

4-Chloro-α-methylbenzyl Alcohol, also known as 1-(4-chlorophenyl)ethanol, is a secondary benzylic alcohol bearing a para-chloro substituent on the aromatic ring and a methyl group at the α-carbon. The α-carbon is a stereocenter, making this compound relevant to chiral synthesis and asymmetric catalysis research. Its molecular formula is C₈H₉ClO with a molecular weight of approximately 156.61 g/mol. The compound is typically presented as a colorless to pale yellow liquid or low-melting solid, depending on enantiomeric form and purity.

Aladdin Scientific supplies this compound under SKU C153305. Researchers should consult the current Certificate of Analysis (CoA) for confirmed purity grade, physical state, and specification details prior to use.

Chemical Properties and Structure

The compound possesses a phenyl ring substituted at the para position with chlorine, attached to a CHOH–CH₃ unit. The secondary hydroxyl group confers reactivity typical of benzylic alcohols: it participates readily in oxidation (to the corresponding ketone, 4-chloroacetophenone), esterification, etherification, and nucleophilic substitution reactions when activated.

The chiral α-carbon means the compound exists as two enantiomers: (R)- and (S)-1-(4-chlorophenyl)ethanol. The racemic mixture is commonly used as a substrate in studies of enantioselective reduction or enzymatic resolution. The para-chloro substituent modulates electronic density on the ring, slightly deactivating it toward electrophilic aromatic substitution while providing a useful handle for cross-coupling or halogen-exchange reactions.

Storage, Handling, and Safety

4-Chloro-α-methylbenzyl Alcohol should be stored in a tightly sealed container under cool, dry conditions, away from strong oxidizing agents, strong acids, and open flames. A storage temperature of 2–8 °C or room temperature in a well-ventilated area is commonly recommended for benzylic alcohols of this class; consult the product SDS for the specific recommendation for C153305.

Standard laboratory personal protective equipment (PPE) is required: chemical-resistant gloves, safety glasses, and a laboratory coat. Operations that generate aerosols or dust should be performed in a fume hood. The compound may cause skin and eye irritation. In case of contact, flush the affected area with water and seek medical advice if irritation persists. Disposal must comply with applicable local regulations for halogenated organic compounds.

Note: Always refer to the Aladdin Scientific Safety Data Sheet (SDS) for C153305 for authoritative hazard classification, first-aid measures, and disposal guidance.

Research and Synthetic Applications

4-Chloro-α-methylbenzyl Alcohol is a versatile building block in organic synthesis. Its primary applications include:

• Asymmetric synthesis substrate: Used to benchmark chiral catalysts and biocatalysts in asymmetric reduction and kinetic resolution studies, given the well-defined single stereocenter.
• Pharmaceutical intermediate: The para-chlorophenylethanol scaffold appears in the synthesis of active pharmaceutical ingredients (APIs) and drug candidates targeting central nervous system and other therapeutic areas.
• Ester and ether synthesis: The secondary hydroxyl can be acylated or alkylated to produce esters and ethers for structure-activity relationship (SAR) studies.
• Oxidation studies: Serves as a model substrate for evaluating alcohol oxidation methodologies, including enzymatic oxidation and metal-catalyzed protocols, with the product being 4-chloroacetophenone.

Researchers should confirm suitability for their specific application by reviewing the CoA for purity and consulting primary literature relevant to the reaction of interest.

Ordering, Purity, and Specification Information

4-Chloro-α-methylbenzyl Alcohol is available from Aladdin Scientific under SKU C153305. When placing an order, researchers and procurement teams should consider:

• Purity grade: Confirm the purity specification listed on the current product page and CoA. For sensitive asymmetric synthesis or analytical reference applications, request the highest available purity grade.
• Pack size: Available pack sizes may vary; contact Aladdin Scientific customer service for custom quantities or bulk pricing.
• Enantiomeric form: Confirm whether the catalog entry supplies the racemate or a specific enantiomer if enantiopure material is required for your application.
• Documentation: CoA, SDS, and NMR or HPLC data may be available upon request or via the product page on the Aladdin Scientific website.

For technical questions regarding this product, contact Aladdin Scientific technical support. For order status, returns, or shipping inquiries, contact customer service directly.

Frequently asked questions

What is the molecular weight and formula of 4-Chloro-α-methylbenzyl Alcohol?

4-Chloro-α-methylbenzyl Alcohol (1-(4-chlorophenyl)ethanol) has the molecular formula C₈H₉ClO and a molecular weight of approximately 156.61 g/mol. These values are consistent with one aromatic ring, one secondary hydroxyl group, one para-chloro substituent, and one methyl group at the α-carbon.

Does 4-Chloro-α-methylbenzyl Alcohol have a chiral center, and is it available as a single enantiomer?

Yes, the α-carbon bearing the hydroxyl and methyl groups is a stereocenter, giving rise to (R)- and (S)-enantiomers. The Aladdin Scientific catalog entry C153305 should be consulted for the specific enantiomeric form supplied. Contact Aladdin Scientific technical support or customer service to inquire about enantiopure material if required for your application.

How should 4-Chloro-α-methylbenzyl Alcohol (C153305) be stored?

The compound should be stored in a tightly sealed container, in a cool and dry location away from strong oxidants, acids, and ignition sources. The precise recommended storage temperature for C153305 is specified in the product SDS available from Aladdin Scientific; generally, 2–8 °C or ambient temperature in a well-ventilated store is suitable for benzylic alcohols of this type. Always check the current SDS for authoritative guidance.

What are the main synthetic uses of 4-Chloro-α-methylbenzyl Alcohol in research?

It is commonly used as a substrate for asymmetric reduction and kinetic resolution studies to evaluate chiral catalysts and biocatalysts, as a pharmaceutical intermediate in the synthesis of APIs containing the 4-chlorophenylethanol motif, and as a model compound in alcohol oxidation methodology research, where it is oxidized to 4-chloroacetophenone. It can also be esterified or etherified for SAR studies.

How do I request a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) for C153305?

Certificates of Analysis and Safety Data Sheets for C153305 (4-Chloro-α-methylbenzyl Alcohol) can typically be accessed via the product page on the Aladdin Scientific website or requested directly from Aladdin Scientific customer service. Providing your lot number when requesting a CoA ensures you receive documentation specific to your batch.

References

1. Aladdin Scientific product page for 4-Chloro-α-methylbenzyl Alcohol, SKU C153305. Aladdin Scientific.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley: New York, 1992. (General reference for benzylic alcohol reactivity and oxidation.)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook reference for secondary alcohol chemistry and stereochemistry.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.