2-Methylphenylacetic acid
[CAS# 644-36-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 2-Methylphenylacetic acid
• Synonyms: o-Tolylacetic acid
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.18
• CAS Registry Number: 644-36-0
• EC Number: 211-416-9
• SMILES: CC1=CC=CC=C1CC(=O)O

Properties

• Melting point: 87-90 °C
• Water solubility: insoluble

Safety Data

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

Hazard Classification

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

Discovery and Applications

2-Methylphenylacetic acid, also known as o-tolylacetic acid, is an organic compound with the formula C9H10O2. It was first synthesized in the early 20th century as part of research into aromatic acids and their derivatives. The compound can be produced through several synthetic routes, including the Friedel-Crafts acylation of toluene followed by oxidation. The discovery of 2-methylphenylacetic acid provided chemists with a valuable intermediate for the synthesis of more complex organic molecules, enabling further exploration of aromatic carboxylic acids.

In the pharmaceutical industry, 2-methylphenylacetic acid serves as an important intermediate in the synthesis of various drugs. Its structure, featuring both an aromatic ring and a carboxylic acid group, makes it useful for creating a range of bioactive compounds. For example, it can be used to synthesize non-steroidal anti-inflammatory drugs (NSAIDs) and other medications that require a phenylacetic acid moiety.

2-Methylphenylacetic acid is also utilized in the agrochemical sector for the development of herbicides and plant growth regulators. Its derivatives can act as active ingredients that influence plant growth, either promoting or inhibiting certain physiological processes.

In the fragrance industry, 2-methylphenylacetic acid is used as an intermediate in the synthesis of various aroma compounds. Its structure allows it to be transformed into esters and other derivatives that possess pleasant floral and fruity odors. These compounds are used in perfumes, cosmetics, and flavorings.

As an intermediate in organic synthesis, 2-methylphenylacetic acid is highly valuable. It can be employed in various chemical reactions, including esterification, amidation, and halogenation, to produce a wide range of functionalized aromatic compounds.

In materials science, 2-methylphenylacetic acid is used to synthesize polymers and advanced materials. Its derivatives can be incorporated into polymer chains to enhance properties such as thermal stability, chemical resistance, and mechanical strength.

2-Methylphenylacetic acid is widely used in academic and industrial research to study new synthetic methodologies and reaction mechanisms. Researchers utilize it as a model compound to explore the effects of substituents on aromatic carboxylic acids and to develop new synthetic routes for complex molecules.

References

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DOI: 10.1007/bf00696982

2019. Synthesis and Herbicidal Activity of Novel β-Methoxyacrylate Derivatives Containing a Substituted Phenylpyridine Moiety. Chemical Research in Chinese Universities, 35(6).
DOI: 10.1007/s40242-019-9128-z

2020. Carbonyl-Photoredox/Metal Dual Catalysis: Applications in Organic Synthesis. Synthesis, 52(22).
DOI: 10.1055/s-0040-1707183