What Is 2-Chloro-5-Chloromethylthiazole and How Is It Used in Chemical Synthesis?
Technical Introduction
2-Chloro-5-Chloromethylthiazole is a chlorinated thiazole derivative with the molecular formula C₅H₃Cl₂NS.
This compound features a thiazole ring substituted with chlorine atoms at the 2-position and a chloromethyl group at the 5-position, which makes it a versatile building block in organic synthesis.
It appears as a colorless to pale yellow liquid or solid depending on purity and storage conditions, with notable reactivity due to its electrophilic chloromethyl and chloro substituents.
Applications
1. Pharmaceutical Intermediate
Used in the synthesis of heterocyclic compounds, which are core structures in many drugs.
Acts as a precursor in developing antimicrobial, antiviral, and anticancer agents.
2. Agrochemical Industry
Serves as a building block for pesticides and herbicides featuring thiazole rings.
3. Specialty Chemical Synthesis
Utilized for introducing thiazole moieties in material science and dye chemistry.
Useful in crosslinking and functionalization reactions due to its reactive chloromethyl group.
Advantages
Dual Reactivity: Chlorine substituent and chloromethyl group allow selective transformations.
Versatility: Suitable for multiple synthetic pathways including nucleophilic substitution.
High Purity: Ensures reproducibility in fine chemical synthesis.
Stable Compound: Can be stored under proper conditions for extended periods.
Typical Parameters
| Property | Value |
|---|---|
| Chemical Formula | C₅H₃Cl₂NS |
| Molecular Weight | 166.04 g/mol |
| Appearance | Colorless to pale yellow liquid/solid |
| Purity (%) | ≥95.0 (typical) |
| CAS Number | 30288-02-3 |
| Boiling Point (°C) | ~140–145 (decomposes) |
| Solubility | Soluble in organic solvents (e.g., DMSO, acetone) |
| Storage | Store in cool, dry, well-ventilated area |
| Shelf Life | 12–24 months (sealed) |
FAQs
Q1: What is the main use of 2-Chloro-5-Chloromethylthiazole?
A1: It is primarily used as an intermediate in pharmaceutical and agrochemical synthesis.
Q2: Is this compound reactive?
A2: Yes, both chlorine atoms and the chloromethyl group confer high electrophilicity.
Q3: How should it be stored?
A3: In a cool, dry place, away from moisture and strong nucleophiles.
Q4: Can it be handled at room temperature?
A4: Yes, but precautions should be taken to avoid exposure and moisture contact.
Q5: Are there any safety concerns?
A5: It is hazardous; use proper PPE and handle in a fume hood.
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