(3-Chlorothiophen-2-yl)methanol: Properties, Handling & Lab Use
(3-Chlorothiophen-2-yl)methanol: Properties, Handling & Lab Use
(3-chlorothiophen-2-yl)methanol is a chlorinated thiophene-based primary alcohol that serves as a versatile heterocyclic building block in organic and medicinal chemistry synthesis workflows.
- Chemical Name
- (3-chlorothiophen-2-yl)methanol
- SKU / Catalog Number
- C175396
- Molecular Formula
- C5H5ClOS
- Molecular Weight
- 148.61 g/mol
- Functional Groups
- Primary alcohol (–CH2OH), chloro substituent, thiophene ring
- Compound Class
- Halogenated heterocyclic alcohol
- Typical Application
- Intermediate for pharmaceuticals, agrochemicals, and materials research
Chemical Identity and Physical Properties
(3-chlorothiophen-2-yl)methanol (molecular formula C5H5ClOS; MW 148.61 g/mol) consists of a thiophene ring bearing a chloro substituent at the 3-position and a hydroxymethyl (–CH2OH) group at the 2-position. The compound is a halogenated heterocyclic primary alcohol. The thiophene ring confers aromatic stability and influences the compound's electronic properties, while the chloro group provides a handle for further functionalization via cross-coupling or nucleophilic substitution reactions. The hydroxymethyl group enables additional derivatization through oxidation, esterification, or etherification. Exact physical constants such as melting point, boiling point, and density should be confirmed from the certificate of analysis (CoA) provided with each lot, as these values can vary with purity.
Synthetic Applications and Research Utility
(3-chlorothiophen-2-yl)methanol is widely used as an intermediate in synthetic organic chemistry. Its dual functionality — a reactive C–Cl bond and a primary alcohol — makes it a highly attractive building block for the preparation of more complex heterocyclic architectures.
- Cross-coupling reactions: The C–Cl bond on the thiophene ring is amenable to palladium- or nickel-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, Stille couplings), enabling the introduction of aryl, vinyl, or alkyl groups.
- Nucleophilic substitution: The chloro substituent can participate in SNAr-type reactions with suitable nucleophiles under appropriate conditions.
- Alcohol derivatization: The –CH2OH group may be oxidized to an aldehyde or carboxylic acid, converted to a halide, protected as an ether, or used to form esters, broadening the range of accessible derivatives.
- Pharmaceutical and agrochemical intermediates: Thiophene-containing scaffolds are prevalent in drug discovery programs; this compound may serve as a precursor to biologically active molecules.
Researchers should consult primary literature for specific reaction conditions and yields, as these are substrate-dependent.
Safe Handling, Storage, and Regulatory Guidance
As with all fine chemical reagents, appropriate safety precautions must be observed when working with (3-chlorothiophen-2-yl)methanol. The following general guidelines apply; always consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for lot-specific hazard information.
- Personal protective equipment (PPE): Wear chemical-resistant gloves, a laboratory coat, and safety goggles. Work in a well-ventilated area or fume hood.
- Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location, away from incompatible materials such as strong oxidizing agents and strong bases. Recommended storage temperature should be confirmed from the product label or CoA.
- Handling: Avoid inhalation of vapors or dust, and avoid contact with skin, eyes, and clothing. Wash hands thoroughly after handling.
- Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing halogenated organic compounds.
- Stability: Keep the container tightly closed when not in use to prevent moisture uptake and degradation.
Review the current SDS before use. Specific hazard classifications and GHS pictograms are detailed therein.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies (3-chlorothiophen-2-yl)methanol under catalog number C175396. Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity, purity, and relevant physicochemical data determined by standard analytical techniques such as NMR, GC, or HPLC. Researchers requiring a specific purity grade should contact Aladdin Scientific's technical team to confirm available specifications before placing an order.
For bulk quantities, custom packaging, or special purity requirements, please reach out to the Aladdin Scientific sales team. Volume pricing may be available for larger orders. Always verify that the most current lot-specific CoA is requested and reviewed prior to use in critical experiments.
Frequently asked questions
What is (3-chlorothiophen-2-yl)methanol used for in research?
(3-chlorothiophen-2-yl)methanol is primarily used as a heterocyclic building block in organic synthesis. Its C–Cl bond supports palladium-catalyzed cross-coupling reactions, while the primary alcohol group enables oxidation, esterification, and other transformations, making it valuable for constructing pharmaceutical and agrochemical intermediates.
How should (3-chlorothiophen-2-yl)methanol be stored to maintain stability?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from strong oxidizers and strong bases. The specific recommended storage temperature is indicated on the product label and CoA for each lot.
What analytical methods are used to verify the purity of C175396?
Aladdin Scientific typically verifies purity using standard analytical techniques including NMR spectroscopy, gas chromatography (GC), and/or HPLC. The results are documented in the Certificate of Analysis (CoA) provided with each lot. Customers should request the CoA at time of ordering.
Is (3-chlorothiophen-2-yl)methanol suitable for cross-coupling reactions?
Yes, the C–Cl bond on the thiophene ring of (3-chlorothiophen-2-yl)methanol makes it a viable substrate for palladium- or nickel-catalyzed cross-coupling reactions such as Suzuki-Miyaura, Negishi, or Stille couplings. Reaction conditions should be optimized for this specific substrate, and researchers are advised to consult relevant literature for guidance.
References
- Aladdin Scientific product page and Certificate of Analysis for (3-chlorothiophen-2-yl)methanol, SKU C175396.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for thiophene chemistry and cross-coupling reactions.)
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (Reference for heterocyclic building blocks including thiophenes.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证(带存储)