Chloroacetyl chloride
Chloroacetyl chloride is an organic compound with the formula ClCH₂COCl. It is a colorless liquid that is used as a building block in the synthesis of various chemical compounds, including pharmaceuticals and agrochemicals.
Structure and Properties[edit | edit source]
Chloroacetyl chloride is a carboxylic acid chloride, characterized by the presence of a carbonyl group (C=O) bonded to a chlorine atom. The molecule is highly reactive due to the presence of the acyl chloride functional group, which makes it susceptible to nucleophilic attack.
The compound is a colorless liquid at room temperature, with a pungent odor. It has a density of 1.42 g/cm³ and a boiling point of 105 °C. Chloroacetyl chloride is highly reactive with water, undergoing hydrolysis to form chloroacetic acid and hydrochloric acid.
Synthesis[edit | edit source]
Chloroacetyl chloride is typically synthesized by the reaction of acetic acid with phosphorus pentachloride (PCl₅) or thionyl chloride (SOCl₂). The reaction proceeds as follows:
- CH₃COOH + PCl₅ → ClCH₂COCl + POCl₃ + HCl
This method is commonly used in industrial settings due to its efficiency and the availability of the reagents.
Applications[edit | edit source]
Chloroacetyl chloride is used in the synthesis of a variety of chemical compounds. It is a key intermediate in the production of herbicides, insecticides, and pharmaceuticals. For example, it is used in the synthesis of chloramphenicol, an antibiotic, and phenoxy herbicides.
The compound is also used in the preparation of chloroacetamides, which are important intermediates in organic synthesis.
Safety and Handling[edit | edit source]
Chloroacetyl chloride is a hazardous chemical that must be handled with care. It is corrosive and can cause severe burns upon contact with skin or eyes. Inhalation of its vapors can lead to respiratory distress and other health issues. Proper personal protective equipment (PPE) such as gloves, goggles, and respirators should be used when handling this compound.
Due to its reactivity with water, chloroacetyl chloride should be stored in a dry, cool place, away from moisture and incompatible substances.
Also see[edit | edit source]
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