2,4-Dinitrotoluene

Base Information

• Chemical Name: 2,4-Dinitrotoluene
• CAS No.: 121-14-2
• Molecular Formula: C7H6N2O4
• Molecular Weight: 182.136
• Hs Code.: 29042030
• European Community (EC) Number: 281-716-2,204-450-0,215-422-2
• ICSC Number: 0727
• NSC Number: 7194
• UN Number: 1600,3454,2038
• UNII: 6741D310ED
• DSSTox Substance ID: DTXSID0020529
• Nikkaji Number: J2.922J
• Wikipedia: 2,4-Dinitrotoluene
• Wikidata: Q416626
• Metabolomics Workbench ID: 52829
• ChEMBL ID: CHEMBL259865
• Mol file: 121-14-2.mol

Synonyms:2,4-dinitrotoluene

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Chemical Property of 2,4-Dinitrotoluene

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1 mm Hg ( 102.7 °C)
• Melting Point: 67-70 °C(lit.)
• Refractive Index: 1.598
• Boiling Point: 299.887 °C at 760 mmHg
• PKA: 13.53 (Perrin, 1972)
• Flash Point: 146.943 °C
• PSA: 91.64000
• Density: 1.408 g/cm³
• LogP: 2.85780
• Storage Temp.: 2-8°C
• Solubility.: Soluble in acetone, ethanol, benzene, ether, and pyrimidine (Weast, 1986)
• Water Solubility.: 0.3 g/L (20 ºC)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 182.03275668
• Heavy Atom Count: 13
• Complexity: 220
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): T, N, F
• Hazard Codes: T,N,F
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: CC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-]
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in the formation of methaemoglobin. This substance is possibly carcinogenic to humans.
• 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.
• 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. A metabolite of TNT (2,4,6-trinitrotoluene). The metabolites of TNT

Technology Process of 2,4-Dinitrotoluene

There total 71 articles about 2,4-Dinitrotoluene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

1-methyl-2-nitrobenzene (88-72-2) → 2,4-dinitrotoluene (121-14-2) + 2,6-dinitrotoluene (606-20-2)

Guidance literature:

With nitric acid; Chloroacetic anhydride; at 50 ℃; for 4h;

Reference yield: 88.0%

toluene (108-88-3,15644-74-3,16713-13-6) → 1-methyl-2-nitrobenzene (88-72-2) + 2,4-dinitrotoluene (121-14-2)

Guidance literature:

With nitric acid; In neat (no solvent); at 90 ℃; for 4h; regioselective reaction;

DOI:10.1039/c5ra11338e

Reference yield: 85.0%

toluene (108-88-3,15644-74-3,16713-13-6) → 2,4-dinitrotoluene (121-14-2) + 2,6-dinitrotoluene (606-20-2)

Guidance literature:

With succinic acid anhydride; nitric acid; at 4 ℃; for 50h; Product distribution / selectivity;

upstream raw materials:

4-methylisopropylbenzene

1-methyl-4-nitrobenzene

1-methyl-2-nitrobenzene

(2,4-dinitro-phenyl)-acetic acid

Downstream raw materials:

2-(2,4-dinitro-styryl)-anthraquinone

1-(2,4-dinitro-phenethyl)-piperidine

2,4-dinitro-3',4'-methylenedioxystilbene

2,4-dinitro-benzaldehyde-(N-m-tolyl oxime )

Refernces

Simple molecule-based fluorescent sensors for vapor detection of TNT

10.1021/ol801030u

This study investigates the synthesis of 1,4-diarylpentaynes (1a-e) and their application as potential sensors for nitroaromatic compounds such as TNT. The researchers synthesized these compounds from 1,4-dichloro or 1,4-difluoro-2,5-diarylbenzene derivatives via a double base-promoted dehydrohalogenation process to form arynes, followed by cycloaddition with anthracene. The resulting 1,4-diarylpentaynes exhibited fluorescence that was quenched in the presence of nitroaromatic vapors, suggesting their potential use in detecting explosives. The study also explored various synthetic approaches, including aryne-anthracene cycloaddition and attempting Pd0-catalyzed coupling reactions, ultimately finding the cycloaddition approach to be effective and scalable. The synthesized compounds were tested in solution and in the solid state, and the results showed that the fluorescence was significantly quenched upon exposure to nitroaromatic compounds such as 2,4-dinitrotoluene (DNT) and TNT, with quenching constants comparable to those of the amplifying polymer. The study concluded that 1,4-diarylpentenylenes could be valuable for developing explosive sensors, and ongoing work is focusing on making such materials and devices.