2,4-Dinitrotoluene
- CAS No.
- 121-14-2
- Chemical Name:
- 2,4-Dinitrotoluene
- Synonyms
- DNT;DINITROTOLUENE;2,4-dnt;1-methyl-2,4-dinitrobenzene;NCI-C01865;Dinitrotoluol;JACS-121-14-2;2,4-dinitrotoluol;2,4-DINITROTOLUENE;2,4-dinitro-toluen
- CBNumber:
- CB7852929
- Molecular Formula:
- C7H6N2O4
- Molecular Weight:
- 182.13
- MOL File:
- 121-14-2.mol
- Modify Date:
- 2024/3/14 15:18:27
| Melting point | 67-70 °C(lit.) |
|---|---|
| Boiling point | 300 °C |
| Density | 1,521 g/cm3 |
| vapor pressure | 1 mm Hg ( 102.7 °C) |
| refractive index | 1.4420 |
| Flash point | 155 °C |
| storage temp. | 2-8°C |
| solubility | Soluble in acetone, ethanol, benzene, ether, and pyrimidine (Weast, 1986) |
| pka | 13.53 (Perrin, 1972) |
| Water Solubility | 0.3 g/L (20 ºC) |
| BRN | 1912834 |
| Henry's Law Constant | 5.39(x 10-8 atm?m3/mol) at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| Stability | Stable. Incompatible with oxidizing agents, reducing agents, strong bases. |
| InChIKey | RMBFBMJGBANMMK-UHFFFAOYSA-N |
| CAS DataBase Reference | 121-14-2(CAS DataBase Reference) |
| IARC | 2B (Vol. 65) 1996 |
| NIST Chemistry Reference | Benzene, 1-methyl-2,4-dinitro-(121-14-2) |
| EPA Substance Registry System | 2,4-Dinitrotoluene (121-14-2) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS06,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301+H311+H331-H341-H350-H361f-H373-H410 | |||||||||
| Precautionary statements | P201-P273-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311 | |||||||||
| Hazard Codes | T,N,F | |||||||||
| Risk Statements | 45-23/24/25-48/22-51/53-62-68-39/23/24/25-11-52/53-36-20/21/22-50/53 | |||||||||
| Safety Statements | 53-45-61-36/37-16-26-60 | |||||||||
| RIDADR | UN 3454 6.1/PG 2 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | XT1575000 | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 6.1 | |||||||||
| PackingGroup | II | |||||||||
| HS Code | 29042030 | |||||||||
| Toxicity | Acute oral LD50 for mice 790 mg/kg, rats 268 mg/kg, guinea pigs 1.30 g/kg (quoted, RTECS, 1985). | |||||||||
| NFPA 704 |
|
2,4-Dinitrotoluene price More Price(9)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 101397 | 2,4-Dinitrotoluene 97% | 121-14-2 | 5G | ₹3196.65 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 101397 | 2,4-Dinitrotoluene 97% | 121-14-2 | 5G | ₹3196.65 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 45969 | 2,4-Dinitrotoluene analytical standard | 121-14-2 | 250MG | ₹4167.25 | 2022-06-14 | Buy |
| Sigma-Aldrich | 101397 | 2,4-Dinitrotoluene 97% | 121-14-2 | 100G | ₹8218.45 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 101397 | 2,4-Dinitrotoluene 97% | 121-14-2 | 100G | ₹8218.45 | 2022-06-14 | Buy |
2,4-Dinitrotoluene Chemical Properties,Uses,Production
Description
2,4-Dinitrotoluene is the most common of the six dinitrotoluene isomers. Dinitrotoluene (DNT) or Dinitro is an explosive with the formula C6H3(CH3)(NO2)2. At room temperature it is a pale yellow to orange crystalline solid. It is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. The first product is mononitrotoluene, DNT is the second, and TNT is the third and final product. Dinitrotoluene induced sensitization in an employee of a manufacturers of explosives, also sensitized to nitroglycerin.
Chemical Properties
2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.
Physical properties
Both 2,4-Dinitrotoulene (2,4-DNT) and 2,6-Dinitrotoluene (2,6-DNT) are man-made solids that are pale yellow and have a slight odor. They are two of the six forms of a chemical called Dinitrotoluene (DNT). DNT is made by mixing toluene with nitric acid.
Uses
2,4-Dinitrotoluene is used largely, along with the 2,6-isomer, to make toluene diisocyanate. The DNT mixture is hydrogenated to yield the diamine that is reacted with phosgene to form the diisocyanate that is reacted with polyols to make polyurethane foams. DNT is also employed to some extent in manufacturing explosives.
Definition
ChEBI: 2,4-dinitrotoluene is a dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.
Production Methods
4-Nitrotoluene is nitrated with mixed acid (containing equimolar HNO3) under controlled conditions and continuous operation to give a 96 % yield of 2,4-dinitrotoluene. In Meissner units, for tighter control of the whole process, cocurrent flow is used in each step to separate mono- and dinitration, but countercurrent flow is used between them to prevent underor overnitration; this is also done in one-step nitration plants. After nitration, if separation of the resulting emulsion is difficult, the introduction of pure product can give surprisingly rapid separation.
Alternative processes yield mixed isomer products. When toluene is nitrated directly under similar conditions with 2.1 equivalents of nitric acid, the product is a ca. 80 : 20 mixture of 2,4-dinitrotoluene and 2,6-dinitrotoluene [606-20-2]. Nitration of 2-nitrotoluene, which is sometimes present in surplus, gives a ca. 67 : 33 mixture of 2,4- and 2,6-dinitrotoluene.
General Description
Heated yellow liquid. Solidifies if allowed to cool. Insoluble in water and more dense than water. Toxic by skin absorption, inhalation and ingestion. Easily absorbed through the skin. Produces toxic oxides of nitrogen during combustion. Used to make dyes and other chemicals.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
DINITROTOLUENE is incompatible with strong oxidizing agents, caustics, active metals, tin and zinc . Decomposition occurs at 250°C. Prolonged heating below 250°C causes some decomposition, and the presence of impurities may decrease the decomposition temperatures. Decomposition is self-sustaining at 280°C. Containers may explode in a fire [USCG, 1999]. May react violently in the presence of a base or when heated to the boiling point. Attacks some forms of plastics, rubbers and coatings .
Health Hazard
Ingestion or overexposure to vapors from hot liquid can cause loss of color, nausea, headache, dizziness, drowsiness, collapse. Hot liquid can burn eyes and skin. Prolonged skin contact with solid can give same symptoms as after inhalation or ingestion.
Safety Profile
2,4-Dintirotoluene is used as an intermediate in the manufacture of polyurethanes. No information is available on the acute (short-term) effects of 2,4-dinitrotoluene in humans. Chronic (long-term) inhalation exposure to 2,4-dinitrotoluene affects the central nervous system (CNS) and blood in humans. A significant reduction in sperm count and normal sperm morphology was observed in one study of chronically exposed workers, while other studies have not reported this effect. No significant increase in cancer mortality was observed in a study of workers occupationally exposed to 2,4-dinitrotoluene by inhalation. Kidney, liver, and mammary gland tumors were observed in animals orally exposed to 2,4- dinitrotoluene. EPA has not classified 2,4-dinitrotoluene for potential carcinogenicity.
Environmental Fate
Biological. When 2,4-dinitrotoluene was statically incubated in the dark at 25 °C with yeast
extract and settled domestic wastewater inoculum, significant biodegradation with gradual
acclimation was followed by deadaptive process in subsequent subcultures. At a concentration of 5
mg/L, 77, 61, 50, and 27% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively. At a concentration of 10 mg/L, only 50, 49, 44, and 23% were observed after 7, 14,
21, and 28-d incubation periods, respectively (Tabak et al., 1981).
Photolytic. Low et al. (1991) reported that nitro-containing compounds (e.g., 2,4-dinitrophenol)
degrade via UV light in the presence of titanium dioxide yielding ammonium, carbonate, and
nitrate ions. By analogy, 2,4-dinitrotoluene should degrade forming identical ions.
Chemical/Physical. Wet oxidation of 2,4-dinitrotoluene at 320 °C yielded formic and acetic
acids (Randall and Knopp, 1980).
Metabolic pathway
The major biliary metabolite of 2,4-dinitrotoluene (2,4- DNT) in the rat is the glucuronide conjugate of 2,4- dinitrobenzyl alcohol and the minor metabolites are 2,4-dinitrobenzyl alcohol, 2,4-dinitrobenzaldehyde, 2- acetylamino-4-nitrotoluene, 4-amino-2-nitro or 2- amino-4-nitrobenzyl alcohol sulfate, 2,4-dinitrobenzoic acid, 2,4-diacetylaminobenzoic acid, and 2-amino-4- nitrobenzoic acid.
Purification Methods
Crystallise it from Me2CO, isopropanol or MeOH. Dry it in a vacuum over H2SO4. It has also been purified by zone melting. It could be EXPLOSIVE when dry.[Beilstein 5 H339, 5 IV 865, 5 III 759.]
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