Methyl 3-bromo-2-methylbenzoate
[CAS# 99548-54-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 3-bromo-2-methylbenzoate
• Synonyms: 3-Bromo-2-methylbenzoic acid methyl ester
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.07
• CAS Registry Number: 99548-54-6
• EC Number: 807-742-1
• SMILES: CC1=C(C=CC=C1Br)C(=O)OC

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.545, Calc.^*
• Boiling Point: 256.3±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 108.8±21.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

Methyl 3-bromo-2-methylbenzoate is an organic compound that belongs to the class of halogenated benzoates. It is characterized by a methyl ester group attached to a benzene ring, which is further substituted with both a bromine atom at the 3-position and a methyl group at the 2-position. The molecular formula of methyl 3-bromo-2-methylbenzoate is C8H9BrO2, and its structure consists of a benzene ring with these two substituents that influence its chemical reactivity and potential applications in various fields of organic synthesis.

The discovery of methyl 3-bromo-2-methylbenzoate can be attributed to conventional synthetic methods for halogenating aromatic compounds. The compound is typically synthesized via an electrophilic aromatic substitution reaction, where a bromine atom is introduced onto the aromatic ring at the meta-position relative to the ester group. This reaction is commonly carried out using bromine or a brominating agent in the presence of a Lewis acid catalyst, such as iron(III) bromide, which facilitates the formation of the bromonium ion intermediate. After the reaction, methyl 3-bromo-2-methylbenzoate is isolated by standard purification methods like recrystallization or chromatography.

Methyl 3-bromo-2-methylbenzoate is used primarily as an intermediate in organic synthesis. Its structure, with the bromo and methyl groups on the aromatic ring, makes it a versatile starting material for various chemical reactions. One of the key features of this compound is its ability to undergo nucleophilic substitution reactions. The bromine atom is an excellent leaving group, allowing for easy replacement by a variety of nucleophiles, including alcohols, amines, and thiols. These reactions can lead to the creation of new derivatives with diverse functional groups, expanding the scope of methyl 3-bromo-2-methylbenzoate's applications.

In the pharmaceutical industry, methyl 3-bromo-2-methylbenzoate has been explored as a precursor for the synthesis of biologically active compounds. The ability to modify the benzene ring and introduce additional functional groups allows chemists to design novel molecules with potential therapeutic properties. Some derivatives of methyl 3-bromo-2-methylbenzoate have been investigated for their antimicrobial, anti-inflammatory, and anticancer activities. The selective modification of the aromatic ring can yield compounds with improved potency and selectivity, making methyl 3-bromo-2-methylbenzoate an important scaffold in drug discovery and development.

In addition to its role in pharmaceuticals, methyl 3-bromo-2-methylbenzoate finds application in materials science, particularly in the synthesis of functionalized polymers. The bromo group is reactive and can participate in polymerization reactions, allowing for the creation of copolymers with tailored properties. These polymers can be used in a variety of applications, including coatings, adhesives, and electronics. Methyl 3-bromo-2-methylbenzoate can also serve as a crosslinking agent or as a starting material for the synthesis of more complex materials with specific electrical or optical properties.

Methyl 3-bromo-2-methylbenzoate also has utility in the field of chemical biology, where it is employed as a reactive probe or a linker in biochemical research. Its ability to undergo nucleophilic substitution reactions makes it useful in the design of targeted drug delivery systems or in the attachment of biomolecules to surfaces for sensing applications. By modifying the ester group or the bromo and methyl substituents, researchers can tailor the properties of the compound to meet the specific needs of chemical biology experiments.

In conclusion, methyl 3-bromo-2-methylbenzoate is a valuable compound in organic synthesis, pharmaceuticals, materials science, and chemical biology. Its reactivity, particularly the ability to undergo nucleophilic substitution, makes it an important intermediate for the preparation of a wide range of derivatives with diverse applications. As demand for new materials and pharmaceuticals continues to grow, methyl 3-bromo-2-methylbenzoate will likely remain an essential building block in the development of innovative compounds and technologies.