99-99-0 Usage
Description
4-Nitrotoluene is an organic compound that is a derivative of toluene with a nitro group attached to the 4th carbon position. It is a pale yellow crystalline solid with a characteristic aromatic smell.
Uses
Used in Chemical Synthesis Industry:
4-Nitrotoluene is used as a chemical intermediate for the synthesis of dyes, explosives, and agricultural chemicals. It serves as a key building block in the production of various organic compounds and materials.
Used in Explosives Industry:
4-Nitrotoluene is used as an explosive material due to its high energy content and ability to detonate when subjected to shock or heat. It is commonly used in the formulation of various types of explosives and propellants.
Used in Dye Manufacturing:
4-Nitrotoluene is used as a precursor in the manufacture of dyes, particularly in the production of azo dyes. Its reactivity and functional groups make it suitable for the synthesis of a wide range of colored compounds.
Used in Toluidine Production:
4-Nitrotoluene is used in the production of toluidines, which are important intermediates in the synthesis of various chemicals, including pharmaceuticals, dyes, and rubber chemicals.
Used in Agricultural Chemicals Industry:
4-Nitrotoluene is used in the manufacture of agricultural chemicals, such as herbicides and pesticides. Its properties make it a versatile building block for the development of effective and targeted agrochemicals.
Used in Rubber Chemicals Industry:
4-Nitrotoluene is used in the production of rubber chemicals, which are essential for the manufacturing of various types of rubber products, including tires, hoses, and seals. Its versatility and reactivity contribute to the development of high-performance rubber compounds.
Synthesis Reference(s)
Journal of the American Chemical Society, 79, p. 5528, 1957 DOI: 10.1021/ja01577a053Tetrahedron Letters, 29, p. 97, 1988 DOI: 10.1016/0040-4039(88)80026-1
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.
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).
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 99-99-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 99-99:
(4*9)+(3*9)+(2*9)+(1*9)=90
90 % 10 = 0
So 99-99-0 is a valid CAS Registry Number.
99-99-0Relevant articles and documents
Intermediate Formation of a ?-Alkyl Iron(III) Complex in the Reduction of 4-Nitrobenzyl Chloride catalysed by Iron(II)-porphyrins
Mansuy, Daniel,Fontecave, Marc,Battioni, Jean-Paul
, p. 317 - 319 (1982)
Formation of the ?-alkyl FeIII (TPP)(CH2C6H4NO2-4) complex (TPP = tetraphenylporphyrin) during reduction of 4-nitrobenzyl chloride (1) by sodium ascorbate catalysed by Fe(TPP)(Cl) was detected by visible spectroscopy, and its involvement as an intermediate in the reduction of (1) to 4-nitrotoluene was deduced from a study of the characteristics of this reaction.
Mechanochemical nitration of toluene with metal oxide catalysts
Dreizin, Edward L.,Schoenitz, Mirko,Vasudevan, Ashvin Kumar
, (2020)
Results of an experimental study of the mechanochemical nitration of toluene are presented. The focus is on the effect of acidity of metal oxide catalysts on the yield of mononitrotoluene. No solvents were used during the reaction. Sodium nitrate served as a source of nitronium. Gas chromatography-mass spectrometry of the products showed that the nitration rate scaled with the catalyst's acidity and specific surface area. Homogenizing NaNO3 with the catalyst by additional milling prior to reaction with toluene led to a rapid, nearly complete nitration. Distribution of nitrate over the surface of catalyst is likely rate limiting when toluene is mechanochemically nitrated without the preliminary milling step. The observed for varied reactant ratios trends in yield and isomer ratios suggest that nitronium participates in the nitration while localized on the active sites of the catalyst. Excess of toluene blocks acid sites, inhibiting the formation of nitronium and impeding the nitration.
Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium
Fauziev, Ruslan V.,Kharchenko, Alexandr K.,Kuchurov, Ilya V.,Zharkov, Mikhail N.,Zlotin, Sergei G.
, p. 25841 - 25847 (2021/08/09)
Regardless of the sustainable development path, today, there are highly demanded chemical productions still operating that bear environmental and technological risks inherited from the previous century. The fabrication of nitro compounds, and nitroarenes in particular, is traditionally associated with acidic wastes formed in nitration reactions exploiting mixed acids. However, nitroarenes are indispensable for industrial and military applications. We faced the challenge and developed a greener, safer, and yet effective method for the production of nitroaromatics. The proposed approach comprises the application of an eco-friendly nitrating agent, namely dinitrogen pentoxide (DNP), in the medium of liquefied 1,1,1,2-tetrafluoroethane (TFE) - one of the most non-hazardous Freons. Importantly, the used TFE is not emitted into the atmosphere but is effortlessly recondensed and returned into the process. DNP is obtainedviathe oxidation of dinitrogen tetroxide with ozone. The elaborated method is characterized by high yields of the targeted nitro arenes, mild reaction conditions, and minimal amount of easy-to-utilize wastes.
The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes
Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi
, p. 18040 - 18049 (2021/05/29)
An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.