4-Nitrotoluene

Chemical Properties

Nitrotoluene is formed in 3 isomeric forms. The o-and m-forms are yellow liquids or solids. The p-form is a pale yellow crystalline solid. All have weak aromatic odors. The Odor Thresholds are: 0.05 mg/L (o-isomer); 1.74 ppm (m-isomer).

Chemical Properties

light yellow crystals

Uses

used in the synthesis of dyestuffs, explosives, and agricultural chemicals

Uses

4-Nitrotoluene is an explosive material.

Uses

manufacture of dyes, toluidines, nitrobenzoic acids, agricultural and rubber chemicals.

Definition

ChEBI: 4-nitrotoluene is a mononitrotoluene that consists of toluene bearing a nitro substituent at the 4-position.

Production Methods

After distillation of the meta fraction from the isomer mixture, the still residues are cooled in a crystallizer to separate technical quality 4-nitrotoluene. Further distillation of nitrotoluene residues and fractions should be implemented with great care because this has been reported to cause explosions. 

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 5528, 1957 DOI: 10.1021/ja01577a053
Tetrahedron Letters, 29, p. 97, 1988 DOI: 10.1016/0040-4039(88)80026-1

General Description

A yellow liquid with a weak aromatic odor. Toxic. Insoluble in water. Combustible but may take some effort to ignite. Produces toxic oxides of nitrogen when burned. In a spill, immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater or nearby streams. Used to make other chemicals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Nitrotoluene may react violently with sodium, tetranitromethane, strong oxidizing agents , sulfuric acid and other acids.

Hazard

Toxic by inhalation, ingestion, skin absorption. Methemoglobinemia. Questionable carcinogen.

Health Hazard

INHALATION, INGESTION, OR SKIN: Headache, flushed face, dizziness, dyspnea (difficult breathing), cyanosis, nausea, vomiting, muscular weakness, rapid pulse and respiration, irritability, and convulsions.

Fire Hazard

Special Hazards of Combustion Products: Yields toxic oxides of nitrogen when burning.

Safety Profile

A poison. Moderately toxic by ingestion, inhalation, and intraperitoneal routes. Mildly toxic by skin contact. Mutation data reported. Combustible when exposed to heat or flame. To fight fire, use CO2, dry chemical, foam. The residue from vacuum distillation may explode spontaneously. Reacts with sodmm to form an ignitable product. Violent reaction with concentrated sulfuric acid (above 16O°C), sulfuric acid + sulfur trioxide (above 52°C). Mixtures with tetranitromethane are sensitive high explosives. May explode on standing. It has been involved in plant scale explosions. When heated to decomposition it emits toxic fumes of NOx. See also other methylnitrobenzene entries and NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Potential Exposure

The nitrotoluenes are used in the production of toluidines and other dye intermediates. All isomers are used in manufacture of agriculture and rubber chemicals and in various dyes.

Environmental Fate

Biological. Under anaerobic conditions using a sewage inoculum, 3- and 4-nitrotoluene both degraded to toluidine (Hallas and Alexander, 1983). Robertson et al. (1992) reported that toluene dioxygenases from Pseudomonas putida F1 and Pseudomonas sp. Strain JS 150 oxidized the methyl group forming 2-methyl-5-nitrophenol and 3-methyl-6-nitrocatechol.
Chemical. Though no products were identified, 4-nitrotoluene (1.5 x 10^-5 M) was reduced by iron metal (33.3 g/L acid washed 18 to 20 mesh) in a carbonate buffer (1.5 x 10^-2 M) at pH 5.9 and 15 °C. Based on the pseudo-first-order disappearance rate of 0.0335/min, the half-life was 20.7 min (Agrawal and Tratnyek, 1996).

Shipping

UN1664 Nitrotoluenes, (o-; m-; p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Dry it in air, then dry it in a vacuum desiccator over H2SO4. [Wright & Grilliom J Am Chem Soc 108 2340 1986, Beilstein 5 IV 848.]

Incompatibilities

Decomposes on contact with strong oxidizers; strong acids; reducing agents; strong bases; ammonia, amines producing toxic fumes, causing fire and explosion hazard. Heat above 190C may cause explosive decomposition. Attacks some plastics, rubbers, and coatings.

Waste Disposal

Controlled incineration-care must be taken to maintain complete combustion at all times. Incineration of large quantities may require scrubbers to control the emission of nitrogen oxides.