![]() The ball-and-stick structure of 2,4-dinitroaniline | |
![]() The chemical structure of 2,4-dinitroaniline | |
Names | |
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Preferred IUPAC name 2,4-Dinitroaniline | |
Other names 1-Amino-2,4-dinitrobenzene | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.322 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 1596 |
CompTox Dashboard (EPA) | |
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Properties | |
C6H5N3O4 | |
Molar mass | 183.123 g·mol−1 |
Appearance | Colorless to yellowish combustible powder |
Density | 1.61 g/cm3 |
Melting point | 187.8 °C (370.0 °F; 460.9 K) |
Boiling point | Decomposes |
0.06 g/L (20 °C) | |
Solubility | Soluble in acetone, ethyl acetate, acetonitrile and most alcohols · insoluble in water |
Acidity (pKa) | -4.53 (conjugate acid) ; 18.46 |
Explosive data | |
Shock sensitivity | Low |
Friction sensitivity | Low |
Detonation velocity | 4,800 m/s [note 1] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Explosive, Flammable, Toxic, Health and Environmental hazards |
GHS labelling: | |
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Danger | |
H228, H300, H310, H330, H373, H411 | |
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 224 °C (435 °F; 497 K) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 285 mg/kg (oral, rat) |
Related compounds | |
Related compounds | 2,4,6-Trinitroaniline |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2,4-Dinitroaniline is a chemical compound with a formula of C6H5N3O4. It is used as an explosive and as a reagent to detect and characterize aldehydes and ketones.
2,4-Dinitroaniline can be prepared by reaction of 1-chloro-2,4-dinitrobenzene with ammonia.
It can be also prepared by the electrophilic aromatic substitution of aniline. Direct nitration should not be used due to the reactivity of aniline. (i.e. It can be protonated to anilinium or oxidized easily.) Instead the acetyl protection should be used.
Compared to aniline, the basicity of 2,4-dinitroaniline is even weaker. It is due to the electron-withdrawing nature of the nitro groups. This makes the pKa of conjugate acid of 2,4-dinitroaniline being even lower than that of hydronium ions, meaning that it is a strong acid.
The protons in the amino group is also much more acidic than that of aniline.
2,4-Dinitroaniline is usually used as an explosive, although the material possess a negative oxygen balance and can be improved by combining it with an oxidizer such as ammonium nitrate. When in pure form, 2,4-Dinitroaniline has a VoD of 4,800 m/s at 1.61 g/cm3 molecular density.
It is also used for the manufacture of certain azo dyes and disperse dyes, as well as in printing ink, toner, and the preparation of preservatives. The compound also finds applications as an intermediate in the synthesis of neutral dyes, sulfur dyes, and organic pigments.
2,4-Dinitroaniline is moderately toxic, with a lethal dose of 285 mg/kg. However, the main danger is that it is explosive and flammable with heat or friction encouraging these properties.
Nitric acid is an inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%.
Trinitrotoluene, more commonly known as TNT (and more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene), is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard comparative convention of bombs and asteroid impacts. In chemistry, TNT is used to generate charge transfer salts.
Picric acid is an organic compound with the formula (O2N)3C6H2OH. Its IUPAC name is 2,4,6-trinitrophenol (TNP). The name "picric" comes from Greek: πικρός (pikros), meaning "bitter", due to its bitter taste. It is one of the most acidic phenols. Like other strongly nitrated organic compounds, picric acid is an explosive, which is its primary use. It has also been used as medicine (antiseptic, burn treatments) and as a dye.
Dinitrogen tetroxide, commonly referred to as nitrogen tetroxide (NTO), and occasionally (usually among ex-USSR/Russian rocket engineers) as amyl, is the chemical compound N2O4. It is a useful reagent in chemical synthesis. It forms an equilibrium mixture with nitrogen dioxide. Its molar mass is 92.011 g/mol.
Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. As confirmed by X-ray crystallography, nitrobenzene is a planar molecule.
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.
Hexanitrobenzene, also known as HNB, is a nitrobenzene compound in which six nitro groups are bonded to all six positions of a central benzene ring. It is a high-density explosive compound with chemical formula C6N6O12, obtained by oxidizing the amine group of pentanitroaniline with hydrogen peroxide in sulfuric acid.
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.
3,3′-Diaminobenzidine (DAB) is an organic compound with the formula (C6H3(NH2)2)2. This derivative of benzidine is a precursor to polybenzimidazole, which forms fibers that are renowned for their chemical and thermal stability. As its water-soluble tetrahydrochloride, DAB has been used in immunohistochemical staining of nucleic acids and proteins.
2,4-Dinitrophenylhydrazine (2,4-DNPH or DNPH) is the organic compound C6H3(NO2)2NHNH2. DNPH is a red to orange solid. It is a substituted hydrazine. The solid is relatively sensitive to shock and friction. For this reason DNPH is usually handled as a wet powder. DNPH is a precursor to the drug Sivifene.
1,3,5-Triazido-2,4,6-trinitrobenzene, also known as TATNB (triazidotrinitrobenzene) and TNTAZB (trinitrotriazidobenzene), is an aromatic high explosive composed of a benzene ring with three azido groups (-N3) and three nitro groups (-NO2) alternating around the ring, giving the chemical formula C6(N3)3(NO2)3. Its detonation velocity is 7,350 meters per second, which is comparable to TATB (triaminotrinitrobenzene).
Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself.
2,4,6-Trinitroaniline, C6H4N4O6, abbreviated as TNA and also known as picramide, a nitrated amine. Materials in this group range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. The appearance of trinitroaniline varies from yellow to orange to red depending on its purity and concentration.
Tetranitromethane or TNM is an organic oxidizer with chemical formula C(NO2)4. Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric acid.
2-Nitrobenzaldehyde is an organic compound with the formula O2NC6H4CHO. It is one of three isomers of nitrobenzaldehyde. It contains a nitro group adjacent to the formyl group.
Trinitroanisole is a chemical compound that exists as pale yellow crystals with a melting point of 68 °C. It is highly toxic. It is an explosive with a detonation velocity of 7200 meters per second. The compound's primary hazard is a blast of an instantaneous explosion, not flying projectiles or fragments.
2,4-Dinitroanisole (DNAN) is a low sensitivity organic compound. It has an anisole (methoxybenzene) core, with two nitro groups (–NO2) attached.
Dinitroanilines are a class of chemical compounds with the chemical formula C6H5N3O4. They are derived from both aniline and dinitrobenzenes. There are six isomers: 2,3-dinitroaniline, 2,4-dinitroaniline, 2,5-dinitroaniline, 2,6-dinitroaniline, 3,4-dinitroaniline, and 3,5-dinitroaniline.
note 1 Calculated from the detonation velocity of 2,4,6-trinitroaniline by multiplying 2/3