Ethyl bromoacetate

Ethyl bromoacetate is a clear, colorless liquid with a fruity, pungent odor[1][2]. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid[2]. This compound is a lachrymator and has been listed by the World Health Organization as a riot control agent[2]. It was first employed for this purpose by French police in 1912 and was also used by the French army during World War I[2].

Applications

Ethyl bromoacetate is a versatile alkylating agent and has a major application in the Reformatsky reaction, where it reacts with zinc to form a zinc enolate[2]. The resulting BrZnCH2CO2Et condenses with carbonyl compounds to give β-hydroxy-esters[2]. It is also the starting point for the preparation of several other reagents, such as the Wittig reagent, which is commonly used to prepare alpha,beta-unsaturated esters from carbonyl compounds[2].

Hazard Summary

Breathing ethyl bromoacetate can irritate the nose and throat, and may irritate the lungs, causing coughing and/or shortness of breath[1]. Higher exposures can cause a build-up of fluid in the lungs (pulmonary edema), a medical emergency, with severe shortness of breath[1]. It can also cause headache, nausea, and vomiting[1]. Skin contact can cause an allergy, leading to itching and a skin rash[1]. Ethyl bromoacetate reacts with water or steam to produce toxic and corrosive gases and is not compatible with oxidizing agents, strong acids, strong bases, and reducing agents[1]. It is a combustible liquid, and poisonous gases are produced in fire, including carbon monoxide and hydrogen bromide[1].

Safety Precautions

Prior to working with ethyl bromoacetate, one should be trained on its proper handling and storage[1]. It should be stored in tightly closed containers in a cool, well-ventilated area away from heat or flames[1]. Sources of ignition, such as smoking and open flames, are prohibited where ethyl bromoacetate is used, handled, or stored[1]. Good work practices, such as changing into clean clothing promptly after contamination and providing eye wash fountains and emergency shower facilities, can help reduce hazardous exposures[1].

Commercial Availability

Ethyl bromoacetate is commercially available as a reagent grade, 98%, with a vapor pressure of 2.6 mmHg at 25°C, and a density of 1.506 g/mL at 25°C[3]. It is insoluble in water and has a refractive index of n20/D 1.451 (lit.)[3]. The compound is classified as dangerous, with acute toxicity by dermal, inhalation, and oral routes, and is also flammable[3].

Citations:

[1] https://nj.gov/health/eoh/rtkweb/documents/fs/0856.pdf

[2] https://en.wikipedia.org/wiki/Ethyl_bromoacetate

[3] https://www.sigmaaldrich.com/US/en/product/aldrich/133973

[4] https://www.emdmillipore.com/us/en/product/ethyl-bromoacetate,mda_chem-801636

[5] https://pubchem.ncbi.nlm.nih.gov/compound/Ethyl-bromoacetate