2-Chloro-5-chloromethyl Thiazole

2-Chloro-5-chloromethyl Thiazole

2-Chloro-5-chloromethyl thiazole (CAS: NA) is an organosulfur compound with the molecular formula C₄H₃Cl₂NS. It features a thiazole ring (a five-membered heterocycle containing sulfur and nitrogen) substituted with a chloro group at the 2-position and a chloromethyl group (–CH₂Cl) at the 5-position. This structure makes it a valuable intermediate in agrochemical and pharmaceutical synthesis.

Key Properties

Chemical Formula: C₄H₃Cl₂NS

Molecular Weight: 168.04 g/mol

Appearance: Colorless to pale yellow liquid (or low-melting solid)

Boiling Point: ~200–220°C (estimated)

Solubility:

Soluble in organic solvents (e.g., DCM, THF, acetone)

Insoluble in water

Applications

Agrochemicals:

Key intermediate in the synthesis of neonicotinoid insecticides (e.g., clothianidin, thiamethoxam).

Used to modify thiazole rings in fungicides and herbicides.

Pharmaceuticals:

Building block for bioactive molecules (e.g., antiviral or antibacterial agents targeting thiazole-based scaffolds).

Material Science:

Potential precursor for conductive polymers or corrosion inhibitors due to sulfur/nitrogen coordination sites.

Safety & Handling

Hazards:

Corrosive (may cause skin/eye burns)

Releases toxic fumes (HCl) if heated or hydrolyzed

Storage: Keep in a cool, dry place under inert atmosphere (N₂/Ar).

PPE: Gloves, goggles, and fume hood required.

Synthesis

From 2-Amino-5-chloromethyl Thiazole:

Diazotization followed by Sandmeyer reaction (chlorination).

Direct Chlorination:

Electrophilic chlorination of 5-methylthiazole (e.g., using SO₂Cl₂).