2-Chloro-1-(4-Chlorophenyl)ethanol: Properties & Applications

2-Chloro-1-(4-chlorophenyl)ethanol is a bifunctional halohydrin intermediate bearing both a reactive aliphatic chloride and a benzylic hydroxyl group on a para-chlorophenyl scaffold, making it a versatile building block in pharmaceutical and agrochemical synthesis.

IUPAC Name

2-Chloro-1-(4-chlorophenyl)ethanol

Molecular Formula

C₈H₈Cl₂O

Molecular Weight

191.05 g/mol

SKU

C695515

Functional Groups

Secondary alcohol, aliphatic chloride, aryl chloride

Key Application

Pharmaceutical intermediate and chiral synthesis building block

Chemical Identity and Physical Properties

2-Chloro-1-(4-chlorophenyl)ethanol (SKU: C695515) belongs to the halohydrin class of organic compounds. Its molecular formula is C₈H₈Cl₂O, giving a molecular weight of approximately 191.05 g/mol. The molecule features a para-chlorophenyl aromatic ring attached to a secondary carbinol carbon, with an additional chloromethyl group at the adjacent carbon. This arrangement creates a substrate with three distinct reactive sites: the aromatic C–Cl bond, the aliphatic C–Cl bond, and the hydroxyl group.

As a halohydrin, the compound can exist as two enantiomers (R and S configurations) at the chiral center bearing the hydroxyl group. The presence of two chlorine atoms at distinct positions (one aryl, one aliphatic) distinguishes their respective reactivities, with the aliphatic chloride generally being far more susceptible to nucleophilic substitution under mild conditions.

Synthesis Relevance and Reactivity

The dual electrophilic character of 2-Chloro-1-(4-chlorophenyl)ethanol makes it particularly attractive in multistep synthetic strategies. The aliphatic C–Cl bond can be displaced by a wide range of nucleophiles—including amines, azides, thiols, and oxygen nucleophiles—to afford diverse structural analogs under standard SN2 conditions. Meanwhile, the free hydroxyl group is amenable to esterification, etherification, or oxidation to yield the corresponding ketone, 2-chloro-1-(4-chlorophenyl)ethanone.

Halohydrins such as this compound also serve as masked epoxide equivalents; treatment with base promotes intramolecular cyclization to generate the corresponding styrene oxide derivative, which can then be ring-opened enantioselectively by various nucleophiles. This epoxide-forming pathway is widely exploited in the synthesis of beta-blockers and other aryloxy propanolamines. The para-chlorophenyl moiety additionally confers useful spectroscopic handles (UV absorption, distinctive NMR patterns) that assist in monitoring reaction progress.

Laboratory Applications and Handling

In laboratory settings, 2-Chloro-1-(4-chlorophenyl)ethanol (C695515) is primarily employed as a synthetic intermediate in the preparation of pharmacologically active compounds, agrochemical building blocks, and fine chemical analogs. Researchers use it to access chiral alpha-aryl epoxides via base-mediated cyclization, or as a direct electrophile for library synthesis in medicinal chemistry programs.

Standard laboratory precautions applicable to halogenated organic compounds apply: work should be conducted in a well-ventilated fume hood, with appropriate personal protective equipment including gloves, safety glasses, and lab coat. The compound should be stored in a tightly sealed container away from moisture and strong bases to prevent premature cyclization or hydrolysis. Compatibility with a range of common solvents (dichloromethane, ethyl acetate, THF, acetonitrile) makes it straightforward to incorporate into existing synthetic protocols.

Ordering and Availability from Aladdin Scientific

2-Chloro-1-(4-chlorophenyl)ethanol is available from Aladdin Scientific under SKU C695515. Researchers and procurement teams can request purity specifications, safety data sheets (SDS), and certificate of analysis (CoA) documentation directly through Aladdin Scientific's ordering portal. For bulk quantities or custom purity requirements, please contact Aladdin Scientific's customer service team.

When placing an order, ensure that the correct SKU (C695515) is referenced to avoid confusion with structurally related chlorophenyl ethanol isomers. Aladdin Scientific is committed to supplying high-purity research reagents with full documentation to support reproducible experimental results.

Frequently asked questions

What is 2-Chloro-1-(4-chlorophenyl)ethanol used for in organic synthesis?

It is primarily used as a bifunctional halohydrin intermediate. Its aliphatic C–Cl bond undergoes SN2 reactions with various nucleophiles, and under basic conditions it can cyclize to form a chiral epoxide, which is valuable in the synthesis of pharmaceutical agents such as beta-blockers and related aryloxy propanolamines.

Does 2-Chloro-1-(4-chlorophenyl)ethanol have a chiral center, and is it available in enantiopure form?

Yes, the compound contains one chiral center at the carbinol carbon, giving rise to R and S enantiomers. Whether enantiopure material is available under SKU C695515 should be confirmed with Aladdin Scientific directly, as catalog offerings may include racemic mixtures or specific enantiomers depending on stock.

How should 2-Chloro-1-(4-chlorophenyl)ethanol be stored to maintain stability?

The compound should be stored in a tightly sealed container under cool, dry conditions, away from moisture, heat, and strong bases. Exposure to base or elevated temperatures may trigger intramolecular cyclization to the epoxide, reducing reagent integrity. Always consult the current SDS and CoA provided by Aladdin Scientific for specific storage conditions.

What solvents are compatible with 2-Chloro-1-(4-chlorophenyl)ethanol?

The compound is generally compatible with common organic solvents including dichloromethane, ethyl acetate, tetrahydrofuran (THF), and acetonitrile, facilitating its use across a broad range of synthetic protocols. Protic solvents and strongly basic aqueous media should be avoided to prevent undesired side reactions.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley, 1992. (General halohydrin chemistry and epoxide formation)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. 2nd ed. Oxford University Press, 2012. (SN2 reactions of halohydrins and nucleophilic substitution)
3. Aladdin Scientific Product Listing: 2-Chloro-1-(4-chlorophenyl)ethanol, SKU C695515. Aladdin Scientific (aladdin-e.com).

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