Ethyl bromoacetate is a chemical compound having the formula CH2BrCO2C2H5. This clear, colorless liquid is an ethyl ester of bromoacetic acid. It is derived from acetic acid in two steps.
This compound is also referred to as antol, ethyl monobromacetate, bromoacetic acid ethyl ester, etc. Its molecular weight is 167.00118 g/mol. Although insoluble in water, the chemical is soluble in acetone, benzene, and alcohol. It is miscible in ethanol, and ethyl ether.
Ethyl bromoacetate boils at 168.5° C and has a flash point of 118° F. When heated, it emits highly toxic fumes of hydrogen bromide. There are three common methods of manufacturing the compound. Interaction of bromine and acetic acid in the presence of red phosphorus gives ethyl bromoacetate.
It is also obtained by the esterification of ethyl alcohol with bromoacetic acid with sulfuric acid acting as a catalyst. The third way is through the esterification of ethanol and bromoacetic acid.
The industrial use of ethyl bromoacetate is as an intermediate. It has been used to make reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in some aqueous medium. These nanoparticles function as a detectable drug carrier. It is also used in the synthesis of metabolites of carcinogenic PAHs.
It is a component of steroidal antiestrogens, prepared through cyclic condensation. It also acts as a reactant in the preparation of antimicrobials and antioxidants. A major application of ethyl bromoacetate is that it reacts with zinc to form zinc enolate.
These varied uses will drive growth of the global and Chinese ethyl bromoacetate industry from 2016 to 2020. However, its high toxicity and flammability could deter demand. Exposure to the chemical leads to several short-term and chronic adverse health effects.
It is on the Hazardous Substances List of regulatory authorities. Manufacturers are required to provide personal protective equipment like faceshields, eyeshields, gloves, etc. to workers. This will increase their costs.
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Key vendors of the global ethyl bromoacetate industry include Aurora Fine Chemicals LLC, ABI Chem, Life Chemicals, Sigma-Aldrich, Wutech, King Scientific, Tokyo Chemical Industry, AK Scientific Inc., and Oakwood Products.
Prominent Chinese manufacturers encompass Shanghai Aladdin Bio-Chem Technology Co. Ltd., Jinxiang Chemical (Danyang) Products Co. Ltd., Nanjing Huang Tai Pharmaceutical Technology Co. Ltd., Jiangsu Dongtai Xinyuan Chemical Co. Ltd., Beijing Ouhe Technology Co. Ltd., and Meryer (Shanghai) Chemical Technology Co. Ltd.