(4-Chlorothiophen-2-yl)methanol: Properties & Lab Use FAQ

(4-chlorothiophen-2-yl)methanol is a halogenated thiophene-based primary alcohol widely used as a versatile synthetic building block in medicinal chemistry, agrochemical research, and heterocyclic compound synthesis.

Chemical Name

(4-Chlorothiophen-2-yl)methanol

Molecular Formula

C5H5ClOS

Molecular Weight

148.61 g/mol

CAS Number

Not confirmed in source — see review flags

Functional Groups

Primary alcohol (–CH2OH) and C–Cl bond on thiophene ring

SKU

C175832

Primary Application

Synthetic intermediate and building block for heterocyclic chemistry

Overview and Chemical Structure

(4-Chlorothiophen-2-yl)methanol (SKU: C175832) is an organosulfur compound featuring a five-membered thiophene ring substituted with a chlorine atom at the 4-position and a hydroxymethyl (–CH2OH) group at the 2-position. This combination of a nucleophilic primary alcohol and an electrophilic C–Cl bond on an electron-rich aromatic heterocycle makes the molecule bifunctional and highly useful in synthetic chemistry.

The thiophene core confers aromatic stability and characteristic electronic properties distinct from benzene, including a lower resonance energy and greater polarizability, which influence its reactivity in cross-coupling and nucleophilic substitution reactions. The chlorine substituent can serve as a handle for palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, Buchwald–Hartwig), while the alcohol can be oxidized, esterified, etherified, or converted to a leaving group.

Physical and Chemical Properties

(4-Chlorothiophen-2-yl)methanol has a molecular formula of C5H5ClOS and a molecular weight of approximately 148.61 g/mol. The compound is expected to be a colorless to pale yellow liquid or low-melting solid at room temperature, consistent with other closely related chlorothiophenemethanol analogues, though researchers should consult the product specification sheet (Certificate of Analysis, CoA) supplied with SKU C175832 for confirmed physical constants including exact melting or boiling point, density, and refractive index.

The hydroxymethyl group renders the compound moderately polar and capable of hydrogen bonding, influencing its solubility profile: it is anticipated to be soluble in common organic solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, and dimethyl sulfoxide, with limited solubility in non-polar solvents and water. The pKa of the benzylic-type alcohol is expected to be in the range typical of primary aromatic alcohols (pKa ~15–16 in DMSO), though this has not been explicitly confirmed in the supplied source material.

Research Applications and Synthetic Utility

(4-Chlorothiophen-2-yl)methanol serves as a valuable bifunctional building block in the synthesis of complex heterocyclic molecules. Its principal utility lies in three complementary areas:

• Cross-coupling chemistry: The aryl C–Cl bond undergoes palladium- or nickel-catalyzed cross-coupling reactions, enabling the introduction of aryl, alkenyl, alkyl, amino, or alkoxy groups at the 4-position of the thiophene ring to expand molecular complexity.
• Alcohol functionalization: The primary –CH2OH group can be oxidized to the corresponding aldehyde (using oxidants such as Dess–Martin periodinane, Swern, or MnO2) or carboxylic acid, mesylated or tosylated to generate activated electrophiles, or converted to halides for further substitution reactions.
• Medicinal and agrochemical research: Thiophene-containing scaffolds are prevalent in pharmaceuticals and crop-protection agents. (4-Chlorothiophen-2-yl)methanol provides a ready entry point for constructing such scaffolds with defined substitution patterns relevant to structure–activity relationship (SAR) studies.

Handling, Storage, and Safety

As with all halogenated organic compounds, standard laboratory safety precautions should be observed when working with (4-chlorothiophen-2-yl)methanol. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for SKU C175832 for complete hazard classifications, GHS pictograms, first-aid measures, and disposal guidance before use.

General handling guidance: Work in a well-ventilated fume hood. Avoid contact with skin, eyes, and clothing. Use appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Avoid open flames if the compound is a liquid with a low flash point — consult the SDS for confirmed flash point data.

Storage: Store in a tightly sealed container away from moisture, light, and heat. Refrigerated storage (2–8 °C) in an inert atmosphere (argon or nitrogen) is recommended to preserve purity and prevent oxidation of the alcohol or degradation of the thiophene ring. Confirm recommended storage conditions on the product label and CoA supplied with your specific lot.

Ordering and Specifications

(4-Chlorothiophen-2-yl)methanol is available from Aladdin Scientific under SKU C175832. When ordering, researchers and procurement teams should note the following:

• Purity: Refer to the current Certificate of Analysis (CoA) for the specific lot purity, determined by techniques such as GC, HPLC, or NMR. Contact Aladdin Scientific customer service to request a CoA for a specific lot number before purchase if purity is critical to your application.
• Available pack sizes: Check the Aladdin Scientific product page for current available quantities. Pack sizes and pricing may vary; bulk quantities may be available upon request.
• Lead time and shipping: Consult the product listing for stock availability. The compound should be shipped with appropriate cold-pack or dry-ice packaging if temperature-sensitive. Review Aladdin Scientific's shipping and delivery policies for international orders.
• Custom synthesis: If a specific purity grade, isotopic label, or custom quantity is required, contact Aladdin Scientific's technical sales team to discuss custom synthesis options.

Frequently asked questions

What is (4-chlorothiophen-2-yl)methanol used for in research?

(4-Chlorothiophen-2-yl)methanol (SKU C175832) is primarily used as a bifunctional synthetic building block. The aryl chloride enables palladium- or nickel-catalyzed cross-coupling reactions, while the primary alcohol can be oxidized, halogenated, or converted into an activated electrophile, making the compound valuable in medicinal chemistry, agrochemical research, and heterocyclic synthesis.

How should (4-chlorothiophen-2-yl)methanol be stored to maintain purity?

The compound should be stored in a tightly sealed container under an inert atmosphere (argon or nitrogen) at 2–8 °C, away from moisture, direct light, and heat sources to prevent oxidation of the alcohol and degradation of the thiophene ring. Always confirm the specific storage conditions stated on the product label and the Certificate of Analysis (CoA) provided with your lot.

What solvents are suitable for dissolving (4-chlorothiophen-2-yl)methanol?

(4-Chlorothiophen-2-yl)methanol is anticipated to be soluble in common polar aprotic and protic organic solvents including dichloromethane, ethyl acetate, tetrahydrofuran (THF), and dimethyl sulfoxide (DMSO). Solubility in water and non-polar solvents such as hexane is expected to be limited. Researchers should verify solubility experimentally under their specific conditions, as solubility can be concentration- and temperature-dependent.

Can the C–Cl bond in (4-chlorothiophen-2-yl)methanol be used in cross-coupling reactions?

Yes. The aryl C–Cl bond at the 4-position of the thiophene ring is a competent electrophilic partner in palladium- and nickel-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig amination. While aryl chlorides are generally less reactive than aryl bromides or iodides, modern catalyst systems with bulky phosphine or NHC ligands readily activate aryl chlorides, making SKU C175832 a cost-effective starting material for complex heterocycle synthesis.

Where can I find the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for SKU C175832?

The Certificate of Analysis and Safety Data Sheet for (4-chlorothiophen-2-yl)methanol (SKU C175832) are available on the Aladdin Scientific product page. You can also contact Aladdin Scientific customer service directly, providing your lot number, to request the most current CoA. Always consult the SDS before handling the compound to ensure compliance with your institution's safety protocols.

References

1. Aladdin Scientific product page for (4-Chlorothiophen-2-yl)methanol, SKU C175832. Aladdin Scientific.
2. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for thiophene chemistry and reactivity.)
3. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis. Angew. Chem. Int. Ed. 2005, 44, 4442–4489. doi:10.1002/anie.200500368

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