Methyl 2-(4-bromophenyl)-2,2-dimethylacetate
[CAS# 154825-97-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 2-(4-bromophenyl)-2,2-dimethylacetate
• Synonyms: 2-(4-Bromophenyl)-2-methylpropionic acid methyl ester
• Molecular Formula: C₁₁H₁₃BrO₂
• Molecular Weight: 257.12
• CAS Registry Number: 154825-97-5
• EC Number: 604-979-0
• SMILES: CC(C)(C1=CC=C(C=C1)Br)C(=O)OC

Properties

• Density: 1.337
• Boiling point: 290 °C
• Flash point: 129 °C

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H317-H319-H335-H412
• Safety Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, with the chemical formula C12H13BrO2, is a notable compound in organic synthesis and medicinal chemistry. This molecule features a brominated phenyl group attached to a dimethylacetate moiety, offering unique properties and applications due to its structure.

The discovery of methyl 2-(4-bromophenyl)-2,2-dimethylacetate is rooted in the broader field of chemical synthesis where such compounds are often used as intermediates. The bromine atom in the phenyl ring enhances the molecule’s reactivity, making it a valuable building block for various chemical transformations. The synthesis of this compound typically involves the introduction of a bromine atom into the phenyl ring of a precursor, followed by esterification with methyl 2,2-dimethylacetate. This synthetic route highlights the compound's utility in creating diverse chemical derivatives.

One of the primary applications of methyl 2-(4-bromophenyl)-2,2-dimethylacetate is as an intermediate in organic synthesis. The bromine atom in the phenyl group provides a functional handle for further chemical modifications, such as cross-coupling reactions. These reactions are crucial in the construction of complex molecules and materials, including pharmaceuticals and agrochemicals. The compound’s ability to undergo nucleophilic substitution and coupling reactions makes it an essential tool for chemists aiming to create new compounds with specific properties.

In the pharmaceutical industry, methyl 2-(4-bromophenyl)-2,2-dimethylacetate is used in the development of new drugs. The bromine atom’s presence can influence the biological activity of the compounds derived from it. For example, the introduction of a bromine atom into a drug molecule can enhance its binding affinity to biological targets or alter its pharmacokinetic properties. This modification is particularly useful in designing molecules with improved efficacy or selectivity.

Additionally, the compound plays a role in materials science, where it is employed in the synthesis of functionalized polymers and materials. The brominated phenyl group can participate in polymerization reactions, leading to the development of new materials with desirable properties. These materials can have applications in various fields, including electronics, coatings, and advanced materials.

The reactivity of methyl 2-(4-bromophenyl)-2,2-dimethylacetate makes it a valuable reagent in chemical research. It is used in studies to explore new reaction mechanisms and to develop new synthetic methodologies. The compound's ability to participate in diverse reactions provides a platform for chemists to investigate novel chemical processes and create innovative solutions in both academic and industrial settings.

Overall, methyl 2-(4-bromophenyl)-2,2-dimethylacetate is a versatile compound with significant applications in organic synthesis, pharmaceutical development, and materials science. Its role as an intermediate in chemical reactions and its influence on the properties of derived compounds underscore its importance in advancing chemical research and practical applications.

References

2012. Efficient Synthesis of 4-Amino-2-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-5-ones: Practical Access to a Novel Chemotype in the Development of DGAT-1 Inhibitors. Synthesis, 44, 14.
DOI: 10.1055/s-0032-1316756