4-Nitrotoluene
[CAS# 99-99-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon nitrite
• Name: 4-Nitrotoluene
• Synonyms: 4-Methylnitrobenzene; p-Nitrophenylmethane; 4-Nitrotoluol
• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.14
• CAS Registry Number: 99-99-0
• EC Number: 202-808-0
• SMILES: CC1=CC=C(C=C1)[N+](=O)[O-]

Properties

• Density: 1.392
• Melting point: 51-54 °C
• Boiling point: 238 °C
• Flash point: 103 °C
• Water solubility: 0.35 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS06;GHS08;GHS09 Danger
• Risk Statements: H301-H311-H331-H373-H411
• Safety Statements: P260-P261-P262-P264-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P316-P319-P321-P330-P361+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H331
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

• Transport Information: UN 3446

Discovery and Applications

4-Nitrotoluene, also known as p-nitrotoluene, is an organic compound with the formula C7H7NO2. It was first synthesized in the mid-19th century during studies on nitration reactions of aromatic compounds. The compound is produced by the nitration of toluene, a process that involves treating toluene with nitric acid and sulfuric acid, resulting in the selective introduction of a nitro group (–NO2) at the para position of the benzene ring relative to the methyl group.

4-Nitrotoluene serves as a crucial intermediate in organic synthesis. The nitro group can be readily reduced to an amino group, forming p-toluidine, which is a building block for many dyes, pigments, and pharmaceuticals. It can also undergo various other transformations, such as nitration, sulfonation, and halogenation

In the pharmaceutical industry, 4-nitrotoluene is used to manufacture active pharmaceutical ingredients (APIs) and intermediates. For instance, the reduction of 4-nitrotoluene to p-toluidine facilitates the production of drugs that contain aromatic amines, including analgesics, antipyretics, and antibiotics.

4-Nitrotoluene is employed in the agrochemical sector to synthesize herbicides, insecticides, and fungicides. The nitro group's chemical reactivity allows for the formulation of compounds that can selectively target specific pests or pathogens without harming the crops.

One of the primary uses of 4-nitrotoluene is in the production of dyes and pigments. The compound is a precursor for the synthesis of azo dyes, which are widely used in the textile industry for coloring fabrics. Its derivatives are also used in the manufacture of pigments for inks, paints, and coatings. The vibrant and stable colors produced from 4-nitrotoluene derivatives are essential for various industrial and consumer applications.

In materials science, 4-nitrotoluene is used to develop advanced materials, including polymers and resins. Its derivatives can be incorporated into polymer chains to enhance the thermal and mechanical properties of the materials.

4-Nitrotoluene is utilized in academic and industrial research to study aromatic nitration mechanisms and develop new synthetic methodologies. Researchers use it as a model compound to explore the effects of nitro groups on the reactivity and properties of aromatic compounds.

References

2007. Decomposition of dinitrotoluene isomers and 2,4,6-trinitrotoluene in spent acid from toluene nitration process by ozonation and photo-ozonation. Journal of Hazardous Materials, 147(1-2).
DOI: 10.1016/j.jhazmat.2006.12.052

2003. Carcinogenic potential of o-nitrotoluene and p-nitrotoluene. Toxicology, 183(1-3).
DOI: 10.1016/s0300-483x(02)00543-7

2005. Transfer hydrogenation using recyclable polymer-supported formate (PSF): Efficient and chemoselective reduction of nitroarenes. Molecular Diversity, 9(4).
DOI: 10.1007/s11030-005-8106-1