Thiophosgene

Thiophosgene—systematically known as thiocarbonyl dichloride—is an analogue of phosgene (COCl₂) in which the oxygen atom is replaced by sulfur; it has the molecular formula CSCl₂, CAS number 463-71-8, and a molecular weight of 114.98.

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Product Introduction

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Key physicochemical properties

Appearance: Thiophosgene is a reddish-yellow oily liquid with a strong, pungent, and foul odor (more offensive than phosgene)
Boiling point: Approx. 73–73.5°C; Melting point: Approx. -56°C
Density: 1.508 g/cm³ (15°C); Refractive index: n²⁰D ≈ 1.548
Solubility: Soluble in diethyl ether, benzene, and chlorinated hydrocarbons; decomposes violently upon contact with water, alcohols, or amines, releasing HCl and H₂S-type by-products
Vapor pressure: Approx. 127 mmHg at 25°C; vapor density is approximately four times that of air, making it prone to accumulation in low-lying areas

Structural and Reaction Characteristics

It has the structure Cl–C(=S)–Cl and contains a thiocarbonyl (C=S) group; it is a key reagent in organic synthesis for introducing the thiocarbonyl moiety.
Typical reactions: reacts with primary amines to form isothiocyanates (R–N=C=S); participates in the construction of heterocycles (such as thiazolinones); serves as an intermediate for thiocarbamate pesticides.
Industrially, it is produced from perchloromethyl mercaptan via reductive elimination using SO₂/KI.

Primary Uses

Pesticide intermediates: Synthesis of diafenthiuron (acaricide) and thiocarbamate insecticides/herbicides
Pharmaceuticals/Dyes: Production of isothiocyanates and sulfur-containing heterocyclic compounds
Laboratory reagents: C=S bond construction, thiocarbonylation reactions

Safety, Storage, and Transportation

Thiophosgene is highly toxic and corrosive: UN 2474, Hazard Class 6.1(a), PG II; H331 (Toxic if inhaled), H302 (Harmful if swallowed), H315/H319 (Causes skin and eye irritation), H335 (May cause respiratory irritation).
Inhalation may cause laryngospasm, chemical pneumonitis, and pulmonary edema; contact causes a burning sensation, coughing, headache, and nausea.
Storage and transport: Store thiophosgene in a sealed, dry, and light-protected environment at 2–8°C; strictly prohibit co-storage with water, alcohols, amines, or strong oxidizing agents.
Spill handling: Do not flush with water; absorb with sand/vermiculite and neutralize with an alkaline solution (e.g., 5% NaOH).
Operations must be conducted in a fume hood or negative-pressure glove box; wear a gas mask (Type A filter cartridge for acidic gases and organic vapors), acid-resistant gloves, and safety goggles.