Chemical Identity and Structure

(2-Chloro-1,3-thiazol-5-yl)methanol consists of a 1,3-thiazole ring bearing a chlorine substituent at the 2-position and a hydroxymethyl (–CH₂OH) group at the 5-position. The thiazole core is a five-membered aromatic heterocycle containing one sulfur and one nitrogen atom, conferring significant π-electron delocalization and the characteristic electron-deficient character of the ring.

The molecular formula is C₄H₄ClNOS with a molecular weight of approximately 149.60 g/mol. The compound is catalogued under Aladdin Scientific SKU C482066 and corresponds to the Sigma-Aldrich reference CDS013997, facilitating straightforward cross-referencing during procurement and literature searches.

The coexistence of two orthogonal reactive sites — the electrophilic C-2 chlorine and the nucleophilic/transformable hydroxymethyl group — makes this molecule particularly attractive as a bifunctional synthetic intermediate.

Physicochemical Properties and Handling

As a low-molecular-weight chlorothiazole alcohol, (2-Chloro-1,3-thiazol-5-yl)methanol is expected to be a solid or low-melting solid at room temperature, though experimentally confirmed melting point data should be verified against the certificate of analysis (CoA) supplied with each lot.

Solubility: The hydroxymethyl group imparts moderate polarity, suggesting reasonable solubility in polar aprotic solvents such as DMSO, DMF, and acetonitrile, as well as in lower alcohols. Aqueous solubility is limited by the hydrophobic thiazole ring and the C–Cl bond.

Stability: Store in a cool, dry environment away from moisture and strong bases or nucleophiles that could displace the C-2 chlorine prematurely. Standard laboratory storage at 2–8 °C under inert atmosphere is recommended to maintain reagent integrity over time.

Safety: Handle with appropriate personal protective equipment (PPE) including gloves, safety glasses, and lab coat. Consult the Safety Data Sheet (SDS) for full hazard classification, first-aid measures, and disposal guidelines before use.

Synthetic Applications and Research Utility

(2-Chloro-1,3-thiazol-5-yl)methanol is valued in synthetic chemistry primarily as a bifunctional heterocyclic building block. Its two reactive handles enable sequential or orthogonal transformations:

• Nucleophilic Aromatic Substitution (SNAr) at C-2: The electron-withdrawing nitrogen and sulfur atoms of the thiazole ring activate the C-2 chlorine toward displacement by amines, alcohols, thiols, and other nucleophiles, enabling the efficient synthesis of 2-substituted thiazole libraries relevant to drug discovery.
• Hydroxymethyl Group Transformations: The –CH₂OH moiety can be oxidized to the corresponding aldehyde or carboxylic acid, converted to a leaving group (e.g., mesylate, tosylate, or halide) for further substitution chemistry, or used directly in esterification and etherification reactions.
• Medicinal Chemistry: The thiazole scaffold is widely represented in bioactive molecules and approved pharmaceuticals. This building block accelerates the preparation of analogue libraries for structure–activity relationship (SAR) studies targeting, for example, kinase inhibition, antimicrobial activity, and antifungal applications.
• Agrochemical Synthesis: Chlorothiazole motifs appear in several commercial herbicides and insecticides; this compound can serve as a key intermediate in the preparation of such agrochemically active structures.

Quality, Purity, and Procurement

Aladdin Scientific offers (2-Chloro-1,3-thiazol-5-yl)methanol under SKU C482066, cross-referenced to Sigma-Aldrich CDS013997, providing researchers with a convenient and verifiable sourcing option. Each lot is accompanied by a Certificate of Analysis (CoA) detailing purity (typically assessed by HPLC or GC), NMR confirmation of structure, and lot-specific physicochemical data.

Researchers and procurement teams should request the CoA and SDS prior to use and verify that purity specifications meet the requirements of their specific application. For sensitive downstream assays — such as biological screening or high-precision catalytic reactions — purity ≥95% is generally advisable.

For volume requirements beyond standard pack sizes, or for custom specifications, contact Aladdin Scientific's technical sales team. When cross-referencing with published literature or other suppliers, the CDS013997 identifier facilitates accurate reagent traceability.