Chloroacetic Acid: A Useful Compound in Organic Synthesis
by Yuvi K - January 7, 2024
What is Chloroacetic Acid?
Chloroacetic acid (CHCl2COOH), also known as monochloroacetic acid, is a widely-used precursor for organic synthesis of drugs and other compounds. It is an organic molecular compound classified as an acetic acid because it contains a carbonyl (C=O) functional group and a carboxyl (COOH) functional group. Normal boiling point of CHCl2COOH is 178°C, and it is slightly soluble in water and other polar solvents.
Synthesis of Chloroacetic Acid
Chloroacetic acid is commercially manufactured through several processes: (i) Cl2 oxidation of acetic acid, (ii) hydration of trichloroacetic acid, (iii) from CHCl3 and NaOH, and (iv) through a Pyrolysis of chloropropionic acid. The most popular and commercially viable method for the synthesis of chloroacetic acid is the chlorination of acetic acid (CH3COOH).
Uses of Chloroacetic Acid
Chloroacetic acid is widely used in organic synthesis of pharmaceuticals, pesticides, yeast metabolites, and other compounds. Organic synthesis involving Chloroacetic acid has become increasingly popular due to its low cost and availability. It is used in the production of derivatives of benzoic acid, aryl-acetic acid, and dicarboxylic acid.It is also used in the production of surfactants for soaps and detergents, as an antioxidant and preservative, and as a fixative for dyes.
Chloroacetic Acid in Pharmaceuticals
Chloroacetic acid is commonly used in the production of pharmaceuticals and antibiotics. It is used to synthesize many antibiotics, such as penicillin, cephalosporin, and erythromycin. It is also used in the synthesis of anti-inflammatory drugs, diuretics, cholesterol-lowering drugs, tranquilizers, and sedatives. Chloroacetic acid is used to produce chiral auxiliaries for asymmetric synthesis, and it is a common component of pharmaceutical intermediates.
Chloroacetic Acid in Pesticides
Chloroacetic acid is frequently used in the synthesis of pesticides and herbicides. It is a major component in the production of glyphosate, a commonly used herbicide. Chloroacetic acid is also used to produce acetamiprid, carbaryl, dimethoate, malathion, and methamidophos, which are commonly used Insecticides.
Safety Precautions
Chloroacetic acid is an irritant and corrosive with a dangerous potential for adverse health impacts. Human exposure to this compound may cause skin, eye, and respiratory irritation, and can lead to severe burns or permanent tissue damage. It is important to use protective equipment, including gloves, eye protection, and respiratory protection, while handling chloroacetic acid. The compound should be kept in a tightly sealed container in a cool, dry place. Spills should be contained and all safety precautions should be followed.
Conclusion
Chloroacetic acid is an important and widely-used compound in organic synthesis. It is used to produce pharmaceuticals, pesticides, yeast metabolites, and other compounds, and is relatively low cost and readily available. However, it is a powerful irritant and corrosive and must be handled with extreme caution. With proper handling, however, chloroacetic acid can be an efficient and useful molecule for organic synthesis.
