2,4-Dinitrotoluene

2,4-Dinitrotoluene
IUPAC name 1-methyl-2,4-dinitro benzene
Identifiers
CAS number	121-14-2 Y
PubChem	8461
ChemSpider	8150 Y
UN number	raztopljen: 1600 tekoč ali trden: 2038
KEGG	C11006 Y
ChEBI	CHEBI:920 Y
ChEMBL	CHEMBL259865 Y
Jmol-3D images	Image 1
SMILES Cc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-]
InChI InChI=1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3 Y Key: RMBFBMJGBANMMK-UHFFFAOYSA-N Y InChI=1/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3 Key: RMBFBMJGBANMMK-UHFFFAOYAC
Properties
Molecular formula	C7H6N2O4
Molar mass	182.13 g mol−1
Appearance	Pale yellow to orange crystalline solid
Density	1.52 g/cm3[1]
Melting point	70 °C[1]
Boiling point	Decomposes at 250–300 °C[1]
Explosive data
Shock sensitivity	Insensitive
Friction sensitivity	Very low
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,4-Dinitrotoluene (DNT) or Dinitro is an organic compound with the formula C₆H₃(CH₃)(NO₂)₂. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly used in the polymer industry.

Isomers of dinitrotoluene

Six isomers are possible for dinitrotoluene. The most common one is 2,4-dinitrotoluene.

The nitration of toluene gives sequentially mononitrotoluene, DNT, and finally TNT. 2,4-DNT is the principal product from dinitration, the other main product being about 30% 2,6-DNT. The nitration of 4-nitrotoluene gives 2,4-DNT.^[2]

Applications

Most DNT is used in the production of toluene diisocyanate which is used to produce flexible polyurethane foams. DNT is hydrogenated to produce toluenediamine, which in turn is phosgenated to form toluene diisocyanate. Other uses include the explosives industry. It is not used by itself as an explosive, but some of the production is converted to TNT.

Dinitrotoluene is frequently used as a plasticizer, deterrent coating, and burn rate modifier in propellants (e.g., smokeless gunpowders). As it is carcinogenic and toxic, modern formulations tend to avoid its use. In this application it is often used together with dibutyl phthalate.^{[citation needed]}

Toxicity

Dinitrotoluenes are highly toxic with a TLV of 1.5 mg/m³. It converts hemoglobin into methemoglobin.

2,4 Dinitrotoluene is also a listed hazardous waste under 40 CFR 261.30. Its United States Environmental Protection Agency (EPA) hazardous waste Number is D030. The maximum concentration that may be contained to not have toxic characteristics is 0.13 mg/L.

References

1. ^ ^{a b c} Record of 2,4-Dinitrotoluene in the GESTIS Substance Database from the IFA, accessed on 9. October 2007
2. ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. doi:10.1002/14356007.a17_411