Methyl 4-bromo-2-methylbenzoate
[CAS# 99548-55-7]

Identification

• Name: Methyl 4-bromo-2-methylbenzoate
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.07
• CAS Registry Number: 99548-55-7
• EC Number: 827-648-4
• SMILES: CC1=C(C=CC(=C1)Br)C(=O)OC

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 273.6±20.0 ºC 760 mmHg (Calc.)^*
• Flash point: 119.3±21.8 ºC (Calc.)^*
• Index of refraction: 1.545 (Calc.)^*

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

Safety Data

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

Hazard Classification

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

Discovory and Applicatios

Methyl 4-bromo-2-methylbenzoate is an organic compound belonging to the class of aromatic esters, which are commonly used in chemical synthesis. The structure consists of a benzene ring with three substituents: a methyl group (-CH₃) at the 2-position, a bromine atom (Br) at the 4-position, and a methoxycarbonyl group (-COOCH₃) at the 1-position. This chemical is part of a broader group of methyl esters, which are known for their versatility and wide range of applications in various chemical processes.

The compound was first synthesized in the early years of organic chemistry research and has since been studied for its utility in synthetic organic chemistry. Its molecular structure allows for specific reactivity in a range of chemical reactions, making it valuable in the synthesis of more complex organic molecules.

Methyl 4-bromo-2-methylbenzoate finds application in several areas of chemical synthesis, primarily as a building block for more complex compounds. One of the key uses of this compound is in the synthesis of substituted benzoates, which can be used in the creation of pharmaceutical compounds, agrochemicals, and other bioactive molecules. The presence of the bromine atom in the molecule provides opportunities for nucleophilic substitution reactions, facilitating the incorporation of other functional groups into the aromatic ring.

The compound has also been studied for its potential use in material science. The unique combination of the bromine and methyl groups attached to the benzene ring can influence the compound's physical properties, such as solubility and stability. These characteristics make it useful in the development of novel materials, including polymers and other materials that require specific functionalization of aromatic rings.

Furthermore, methyl 4-bromo-2-methylbenzoate is employed in the synthesis of other specialty chemicals that are used in fine chemical production. Its reactivity with various reagents allows for the creation of a wide array of derivatives that are applied in the pharmaceutical industry, particularly in the design of compounds with specific molecular structures required for drug development.

In addition to its synthetic uses, methyl 4-bromo-2-methylbenzoate also plays a role in the study of reaction mechanisms and chemical processes. Researchers use it to better understand the effects of different substituents on the reactivity of aromatic compounds, as well as the impact of electron-withdrawing and electron-donating groups on reaction outcomes.

Overall, methyl 4-bromo-2-methylbenzoate is a versatile and important intermediate in organic synthesis. It is particularly valuable in the preparation of complex organic molecules and in the study of reaction mechanisms in the synthesis of pharmaceuticals, agrochemicals, and advanced materials.