methyl 5-amino-2-bromo-4-methylbenzoate(CAS: 474330-54-6)

Methyl 5-amino-2-bromo-4-methylbenzoate is a crystalline compound with a molecular weight of approximately 262.05 g/mol. It is slightly soluble in water but readily soluble in organic solvents like ethanol and acetone. The compound is known for its reactivity towards nucleophiles and electrophiles due to its amino and bromo functionalities. It has a melting point around 100-110°C and a pKa of about 8.0 due to the basic nature of the amino group.

Methyl 5-amino-2-bromo-4-methylbenzoate is typically synthesized through a multi-step process involving the bromination of 4-methylbenzoic acid, followed by the acylation with methylamine. Commonly, N-bromosuccinimide (NBS) is used as a brominating agent, and the acylation step employs a mild base like triethylamine. The overall reaction provides a yield of approximately 85% and is carried out under mild conditions to ensure selectivity.

Methyl 5-amino-2-bromo-4-methylbenzoate finds applications in the pharmaceutical industry, where it is used as an intermediate in the synthesis of various drugs. It is also utilized in the polymer industry for modifying the properties of polymers, and in the sensor industry for its potential in gas detection. Additionally, it has potential uses in the semiconductor industry for its electronic properties.

When handling methyl 5-amino-2-bromo-4-methylbenzoate, it is essential to use personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated fume hood to avoid inhalation of vapors. Spills should be cleaned up immediately using appropriate absorbents and disposed of according to local regulations. Always consult the Safety Data Sheet (SDS) for detailed handling and storage instructions.