3-Methyl-2-nitrobenzoic acid
[CAS# 5437-38-7]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon nitrite
• Name: 3-Methyl-2-nitrobenzoic acid
• Synonyms: 2-Nitro-m-toluic acid
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• CAS Registry Number: 5437-38-7
• EC Number: 226-610-9
• SMILES: CC1=C(C(=CC=C1)C(=O)O)[N+](=O)[O-]

Properties

• Water solubility: <0.1 g/100 mL at 22 °C
• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 220-223 °C (Expl.)
• Index of Refraction: 1.601, Calc.^*
• Boiling Point: 340.0±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 153.4±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

Discovery and Applications

3-Methyl-2-nitrobenzoic acid, with the chemical formula C7H7NO4, is a derivative of benzoic acid, where a methyl group and a nitro group are attached to the benzene ring. The compound is commonly used in organic synthesis due to the reactivity of the nitro group, which can undergo various chemical reactions. This compound plays an important role in the synthesis of a range of aromatic compounds and has applications in industries such as pharmaceuticals and agrochemicals.

The discovery of 3-methyl-2-nitrobenzoic acid can be traced back to early synthetic organic chemistry, where researchers sought to explore the properties and reactivity of substituted benzoic acids. The nitro group is a powerful electron-withdrawing group, which alters the electronic properties of the aromatic ring, making it more reactive in certain reactions. The position of the methyl and nitro groups on the benzene ring is significant because it influences the compound's reactivity and its ability to participate in various organic transformations.

3-Methyl-2-nitrobenzoic acid is frequently used in the synthesis of more complex chemical compounds. The presence of both a methyl group and a nitro group allows for selective reactions, such as electrophilic substitution, where the nitro group can direct further substitution to specific positions on the benzene ring. This property makes it useful in the preparation of various aromatic derivatives that have applications in materials science, pharmacology, and other fields of chemistry.

In pharmaceutical chemistry, 3-methyl-2-nitrobenzoic acid and its derivatives are studied for their potential bioactivity. While it is not widely used directly as a drug, its chemical properties make it a useful intermediate in the synthesis of other biologically active compounds. The nitro group in particular is of interest for its ability to undergo reduction reactions, which can lead to the formation of new chemical entities with potentially useful pharmacological properties.

Furthermore, 3-methyl-2-nitrobenzoic acid is also used in the field of agrochemicals, where it can serve as a building block in the synthesis of pesticides and herbicides. The reactivity of the nitro group, along with the ability to modify the methyl group, makes this compound a valuable precursor for the development of new agrochemical agents.

Overall, 3-methyl-2-nitrobenzoic acid is an important chemical intermediate, widely used in organic synthesis for the preparation of various functionalized aromatic compounds. Its primary applications are in the fields of pharmaceuticals and agrochemicals, where it serves as a building block for more complex molecules.

References

Multimodal action of KRP203 on phosphoinositide kinases in vitro and in cells Biochemical and Biophysical Research Communications, 2023-10-30, PMCID: PMC10559341, PMID: 37683456
DOI: 10.1016/j.bbrc.2023.08.050

Predicting corrosion inhibition efficiencies of small organic molecules using data-driven techniques npj Materials Degradation, 2023-08 -09
DOI: 10.1038/s41529-023-00384-z

A quantitative high-throughput screen identifies compounds that lower expression of the SCA2-and ALS-associated gene ATXN2 The Journal of Biological Chemistry, 2022-08, PMCID: PMC9356275, PMID: 35787375
DOI: 10.1016/j.jbc.2022.102228