Ethyl bromoacetate

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EsterStabilisedWittigScheme

Ethyl bromoacetate is a chemical compound with the formula C2H5O2CBr. It is an ester formed from acetic acid and ethanol with bromine substituting for a hydrogen atom on the acetic acid chain. This compound is notable for its use in organic synthesis, particularly in the preparation of alkylating agents and in the synthesis of homologation of carboxylic acids. Ethyl bromoacetate is a colorless liquid with a pungent odor, and it is highly toxic and a lachrymator.

Properties

Ethyl bromoacetate has a boiling point of 167-169 °C and a density of 1.507 g/cm³ at 20 °C. It is poorly soluble in water but highly soluble in organic solvents such as ethanol, diethyl ether, and chloroform. Due to its reactivity, it must be handled with care, as it is a potent lachrymator and can cause severe irritation to the skin, eyes, and respiratory system.

Synthesis

Ethyl bromoacetate is typically synthesized through the reaction of ethanol with bromoacetyl bromide, or by the reaction of acetic acid with ethanol in the presence of sulfuric acid as a catalyst, followed by halogenation with bromine.

Applications

In organic chemistry, ethyl bromoacetate is used as an alkylating agent to introduce the ethyl group into molecules, making it a valuable reagent in the synthesis of various organic compounds. It is also employed in the synthesis of vitamins, pharmaceuticals, and pesticides. Additionally, it serves as a starting material in the homologation process of carboxylic acids to form β-keto esters.

Safety

Ethyl bromoacetate is highly toxic and can be fatal if inhaled or absorbed through the skin. It is also a strong irritant, capable of causing severe burns to the skin and eyes. Proper safety precautions must be taken when handling this chemical, including the use of personal protective equipment (PPE) such as gloves, goggles, and respiratory protection. It is important to work with ethyl bromoacetate in a well-ventilated area or under a fume hood to minimize exposure to its vapors.