Ethyl 3-Amino-4-Fluorobenzoate: Properties, Uses, and Applications
Ethyl 3-amino-4-fluorobenzoate, also known by its CAS number 455-75-4, is a chemical compound that belongs to the family of benzoic acid derivatives. It is a white to off-white crystalline powder with a molecular weight of 195.19 g/mol and a melting point of 91-95°C. This article aims to explore the properties, uses, and applications of Ethyl 3-amino-4-fluorobenzoate.
Properties of Ethyl 3-amino-4-fluorobenzoate
Ethyl 3-amino-4-fluorobenzoate has several distinct properties that make it useful in various applications. It is soluble in most organic solvents, including ethanol, methanol, chloroform, and acetone, but insoluble in water. The compound is stable under normal conditions but may decompose when exposed to heat, light, or moisture. It has a pKa of 4.23 and a logP of 2.11, indicating a moderate lipophilicity.
Uses of Ethyl 3-amino-4-fluorobenzoate
Ethyl 3-amino-4-fluorobenzoate is a versatile compound that has several uses in different industries. Here are some of its common applications:
Pharmaceutical Industry
One of the primary uses of Ethyl 3-amino-4-fluorobenzoate is in the pharmaceutical industry. It is used as an intermediate in the synthesis of various drugs, including anticonvulsants, antipsychotics, and antidepressants. For example, it is a key intermediate in the production of Fluoxetine, a selective serotonin reuptake inhibitor (SSRI) used to treat depression, anxiety, and other mental disorders.
Agrochemical Industry
Ethyl 3-amino-4-fluorobenzoate is also used in the agrochemical industry as an intermediate in the production of herbicides, fungicides, and insecticides. For instance, it is a building block in the synthesis of Flucarbazone-sodium, a herbicide used to control weeds in wheat and barley crops.
Other Applications
Apart from its use in the pharmaceutical and agrochemical industries, Ethyl 3-amino-4-fluorobenzoate has other applications as well. It is used as a fluorescent labeling reagent, a dye intermediate, and a polymer modifier. Additionally, it is employed in the synthesis of various organic compounds, including benzimidazoles, benzoxazoles, and benzothiazoles.
Manufacturing Process of Ethyl 3-amino-4-fluorobenzoate
Ethyl 3-amino-4-fluorobenzoate is manufactured through a series of chemical reactions. The process involves the reaction of 4-fluoronitrobenzene with ethyl chloroformate in the presence of a base such as sodium hydride, potassium carbonate, or triethylamine. The resulting intermediate, ethyl 4-fluoro-3-nitrobenzoate, is then reduced using a reducing agent like iron powder or tin (II) chloride to form Ethyl 3-amino-4-fluorobenzoate.
Safety and Handling of Ethyl 3-amino-4-fluorobenzoate
Ethyl 3-amino-4-fluorobenzoate should be handled with care due to its potential hazards. It may cause skin and eye irritation and is harmful if ingested or inhaled. Therefore, proper personal protective equipment, including gloves, goggles, and respiratory protection, should be worn when handling the compound. It should also be stored in a cool, dry, and well-ventilated area away from sources of heat, light, and moisture.
Conclusion
In summary, Ethyl 3-amino-4-fluorobenzoate is a useful compound with various applications in different industries, particularly in the pharmaceutical and agrochemical sectors. It is a versatile intermediate in the synthesis of several drugs, herbicides, and insecticides. Apart from its industrial uses, it is also employed in other applications, including fluorescent labeling, dye intermediates, and polymer modification. However, it should be handled with care due to its potential hazards and stored appropriately.
