2Bromoethanoic

2-Bromoethanoic acid, also known as bromoacetic acid, is an organobromine compound with the chemical formula CH2BrCOOH. It is a colorless crystalline solid that is soluble in water and polar organic solvents. The compound is a strong acid, with a pKa of 2.86, making it significantly more acidic than acetic acid.

2-Bromoethanoic acid is synthesized by the bromination of acetic acid, typically using elemental bromine in the presence of a catalyst like phosphorus tribromide. The reaction proceeds through an enol intermediate.

Due to the presence of the reactive bromine atom adjacent to the carboxyl group, 2-bromoethanoic acid is a versatile alkylating agent. It readily reacts with nucleophiles, such as amines, thiols, and alcohols, to form substituted acetic acid derivatives. This reactivity makes it a valuable intermediate in organic synthesis for the preparation of various pharmaceuticals, agrochemicals, and dyes. For example, it is used in the synthesis of malonic acid derivatives and alpha-amino acids.

However, 2-bromoethanoic acid is also a toxic and corrosive substance. It can cause severe burns on contact with skin and eyes and is harmful if inhaled or ingested. Proper handling procedures, including the use of personal protective equipment and working in a well-ventilated area, are essential when dealing with this compound. Its corrosive nature also requires careful consideration in storage and disposal.