5-Bromo-3-(hydroxymethyl)benzoic acid methyl ester
[CAS# 307353-32-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 5-Bromo-3-(hydroxymethyl)benzoic acid methyl ester
• Synonyms: methyl 3-bromo-5-(hydroxymethyl)benzoate
• Molecular Formula: C₉H₉BrO₃
• Molecular Weight: 245.07
• CAS Registry Number: 307353-32-8
• SMILES: COC(=O)C1=CC(=CC(=C1)CO)Br

Properties

• Solubility: Slightly soluble (5.6 g/L) (25 ºC), Calc.^*
• Density: 1.557±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.577, Calc.^*
• Boiling Point: 354.2±32.0 ºC (760 mmHg), Calc.^*
• Flash Point: 168.0±25.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

5-Bromo-3-(hydroxymethyl)benzoic acid methyl ester is an organic compound that belongs to the class of substituted benzoic acids. This compound consists of a benzoic acid core with a bromine atom at the 5-position, a hydroxymethyl group at the 3-position, and a methyl ester group attached to the carboxyl group. The functional groups present in the structure contribute to the molecule's reactivity and make it an interesting compound for various chemical and pharmaceutical applications.

The discovery of 5-bromo-3-(hydroxymethyl)benzoic acid methyl ester is part of the broader effort to modify benzoic acid derivatives for use in medicinal chemistry and organic synthesis. The bromine atom in the molecule often serves to enhance the reactivity of the aromatic ring, while the hydroxymethyl group and methyl ester offer opportunities for further functionalization or conjugation with other chemical entities. This combination of groups contributes to the compound’s versatility and has made it an attractive target for synthetic chemists.

In medicinal chemistry, 5-bromo-3-(hydroxymethyl)benzoic acid methyl ester has potential applications as an intermediate in the synthesis of bioactive compounds. The hydroxymethyl group is a functional group that can be easily manipulated in organic synthesis to form more complex molecules. This makes 5-bromo-3-(hydroxymethyl)benzoic acid methyl ester an important building block in the design of new pharmaceuticals. Additionally, the presence of the bromine atom can facilitate reactions such as nucleophilic substitution, allowing for the incorporation of various functional groups that may enhance the compound’s biological activity.

The methyl ester functionality in 5-bromo-3-(hydroxymethyl)benzoic acid methyl ester is another important feature, as it allows the compound to be used in esterification reactions or as a precursor for the synthesis of amides, carboxylic acids, and other derivatives. The methyl ester group can be hydrolyzed under basic or acidic conditions, making it a useful compound for creating various other substituted benzoic acid derivatives.

5-bromo-3-(hydroxymethyl)benzoic acid methyl ester also finds application in the development of agrochemicals. As with many other benzoic acid derivatives, this compound can be modified to produce herbicides, fungicides, or plant growth regulators. The versatility of the hydroxymethyl group allows for structural modifications that may lead to enhanced activity or selectivity in agricultural applications.

In materials science, the compound may serve as a precursor for the synthesis of functionalized polymers or other materials with specific properties. The bromine atom and the hydroxymethyl group can participate in polymerization reactions, contributing to the design of specialty materials for use in coatings, adhesives, or other industrial applications.

In conclusion, 5-bromo-3-(hydroxymethyl)benzoic acid methyl ester is a versatile and reactive compound with potential applications in organic synthesis, medicinal chemistry, agrochemical development, and materials science. The presence of functional groups such as the bromine atom, hydroxymethyl group, and methyl ester allows for a wide range of chemical modifications, making it a valuable intermediate in the synthesis of more complex compounds with targeted properties.