2-Methyl-3-nitrobenzoic acid
[CAS# 1975-50-4]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon nitrite
• Name: 2-Methyl-3-nitrobenzoic acid
• Synonyms: 3-Nitro-o-toluic acid
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• CAS Registry Number: 1975-50-4
• EC Number: 217-826-4
• SMILES: CC1=C(C=CC=C1[N+](=O)[O-])C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 182-184 °C (Expl.)
• Index of Refraction: 1.601, Calc.^*
• Boiling Point: 337.1±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 151.9±13.0 °C, Calc.^*

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

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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Methyl-3-nitrobenzoic acid is an organic compound that belongs to the class of substituted benzoic acids. It consists of a benzene ring with two substituents: a methyl group at the second position and a nitro group at the third position. The compound is also known by other names such as 3-nitro-o-toluic acid.

The discovery of 2-methyl-3-nitrobenzoic acid follows the historical development of substituted benzoic acids, a group of compounds that has been extensively studied due to their widespread presence in organic chemistry and their diverse reactivity. This compound is one of many examples of substituted aromatic acids, which have long been of interest in both industrial and academic chemistry due to their versatile reactivity and applications.

The synthesis of 2-methyl-3-nitrobenzoic acid is typically achieved through nitration of 2-methylbenzoic acid, a process that involves the introduction of a nitro group (-NO2) to the aromatic ring. The nitration reaction typically uses a mixture of concentrated nitric acid and sulfuric acid, which is a standard method for the introduction of nitro groups into aromatic compounds. This synthetic pathway allows for the preparation of the compound in a controlled manner, and such reactions are widely used in the synthesis of various nitrated aromatic compounds.

2-Methyl-3-nitrobenzoic acid has been utilized in several fields of chemistry, particularly in the synthesis of more complex organic molecules. Its reactivity and the presence of both a carboxyl group (-COOH) and a nitro group (-NO2) make it useful as an intermediate in the synthesis of other chemicals, including dyes, pharmaceuticals, and agrochemicals. It may also be involved in the preparation of other substituted benzoic acids or aromatic compounds with more elaborate functional groups.

The compound has potential applications in the synthesis of herbicides and other agrochemicals. Many nitro-substituted aromatic acids and their derivatives are known for their biological activity, which can influence various agricultural and environmental processes. Additionally, it can serve as a precursor for the synthesis of certain drugs and compounds used in chemical research.

While 2-methyl-3-nitrobenzoic acid has been explored for various uses, its primary significance remains in the context of synthetic organic chemistry, where it serves as an important building block for the creation of more complex molecules. The presence of the nitro group allows for further chemical modifications, enabling the development of a range of chemical products and facilitating the study of reaction mechanisms involving aromatic compounds.

Overall, 2-methyl-3-nitrobenzoic acid is a well-established compound in the field of organic chemistry, valued for its role as an intermediate in the synthesis of other chemical substances and its utility in various applications, particularly in the creation of functionalized aromatic compounds.

References

1998. Synthesis of antineoplaston A10 analogs as potential antitumor agents. Archives of Pharmacal Research, 21(2).
DOI: 10.1007/bf02974021

2002. Determination of 2-methyl-3-nitrobenzoic acid through pretreatment with diazomethane by gas chromatography. Se pu = Chinese Journal of Chromatography, 20(5).
PMID: 16358702

2010. (Methanol-κO)(2-methyl-3-nitrobenzoato-κO)triphenyltin(IV). Acta Crystallographica Section E, 66(Pt 9).
DOI: 10.1107/s1600536810033623