2,4-Dinitroaniline

Last updated
2,4-Dinitroaniline [1] [2]
2,4-Dinitroaniline-3D-balls.png
The ball-and-stick structure of 2,4-dinitroaniline
2,4-Dinitroanilin.svg
The chemical structure of 2,4-dinitroaniline
Names
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-553-5
KEGG
PubChem CID
RTECS number
  • BX9100000
UNII
UN number 1596
  • InChI=1S/C6H5N3O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H,7H2
    Key: LXQOQPGNCGEELI-UHFFFAOYSA-N
  • C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])N
Properties
C6H5N3O4
Molar mass 183.123 g·mol−1
AppearanceColorless 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:
GHS-pictogram-explos.svg GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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)
3
1
3
Flash point 224 °C (435 °F; 497 K)
Lethal dose or concentration (LD, LC):
285 mg/kg (oral, rat)
Related compounds
Related compounds
2,4,6-Trinitroaniline

4-Nitroaniline

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.

Contents

Preparation

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.

Basicity

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.

Uses

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.

Safety

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.

See also

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

Nitric acid is the inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast 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%.

<span class="mw-page-title-main">Ammonium nitrate</span> Chemical compound with formula NH4NO3

Ammonium nitrate is a chemical compound with the chemical formula NH4NO3. It is a white crystalline salt consisting of ions of ammonium and nitrate. It is highly soluble in water and hygroscopic as a solid, although it does not form hydrates. It is predominantly used in agriculture as a high-nitrogen fertilizer. Global production was estimated at 21.6 million tonnes in 2017.

<span class="mw-page-title-main">Dimethylaniline</span> Chemical compound

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.

<span class="mw-page-title-main">Aniline</span> Organic compound (C₆H₅NH₂); simplest aromatic amine

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.

<span class="mw-page-title-main">Nitrous acid</span> Chemical compound

Nitrous acid is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite salts. Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes.

<i>p</i>-Phenylenediamine Chemical compound

p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.

<span class="mw-page-title-main">Nitration</span> Chemical reaction which adds a nitro (–NO₂) group onto a 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.

<span class="mw-page-title-main">Polyaniline</span>

Polyaniline (PANI) is a conducting polymer and organic semiconductor of the semi-flexible rod polymer family. The compound has been of interest since the 1980s because of its electrical conductivity and mechanical properties. Polyaniline is one of the most studied conducting polymers.

<span class="mw-page-title-main">Ceric ammonium nitrate</span> Chemical compound

Ceric ammonium nitrate (CAN) is the inorganic compound with the formula (NH4)2[Ce(NO3)6]. This orange-red, water-soluble cerium salt is a specialised oxidizing agent in organic synthesis and a standard oxidant in quantitative analysis.

<span class="mw-page-title-main">Silver fulminate</span> High explosive used in bang snaps

Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.

<span class="mw-page-title-main">Azo compound</span> Organic compounds with a diazenyl group (–N=N–)

Azo compounds are organic compounds bearing the functional group diazenyl.

<span class="mw-page-title-main">Tollens' reagent</span> Chemical reagent used to distinguish between aldehydes and ketones

Tollens' reagent is a chemical reagent used to distinguish between aldehydes and ketones along with some alpha-hydroxy ketones which can tautomerize into aldehydes. The reagent consists of a solution of silver nitrate, ammonium hydroxide and some sodium hydroxide. It was named after its discoverer, the German chemist Bernhard Tollens. A positive test with Tollens' reagent is indicated by the precipitation of elemental silver, often producing a characteristic "silver mirror" on the inner surface of the reaction vessel.

<span class="mw-page-title-main">3,3'-Diaminobenzidine</span> Chemical compound

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.

<span class="mw-page-title-main">Azo dye</span> Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group, but some dyes contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60-70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.

<span class="mw-page-title-main">Diazonium compound</span> Group of organonitrogen compounds

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N+≡N]X where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide.

The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also forms a part of nitric acid and nitrate salts. Nitrogen compounds also have an important role in organic chemistry, as nitrogen is part of proteins, amino acids and adenosine triphosphate.

<span class="mw-page-title-main">Barium chlorate</span> Chemical compound

Barium chlorate, Ba(ClO3)2, is the barium salt of chloric acid. It is a white crystalline solid, and like all soluble barium compounds, irritant and toxic. It is sometimes used in pyrotechnics to produce a green color. It also finds use in the production of chloric acid.

<span class="mw-page-title-main">Lead(II) thiocyanate</span> Chemical compound

Lead(II) thiocyanate is a compound, more precisely a salt, with the formula Pb(SCN)2. It is a white crystalline solid, but will turn yellow upon exposure to light. It is slightly soluble in water and can be converted to a basic salt (Pb(CNS)2·Pb(OH)2 when boiled. Salt crystals may form upon cooling. Lead thiocyanate can cause lead poisoning if ingested and can adversely react with many substances. It has use in small explosives, matches, and dyeing.

<span class="mw-page-title-main">Dinitroaniline</span> Class of chemical compounds

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.

References

  1. "2,4-Dinitroaniline CAS#: 97-02-9". www.chemicalbook.com. Retrieved 2019-03-23.
  2. PubChem. "2,4-Dinitroaniline". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-03-23.

note 1 Calculated from the detonation velocity of 2,4,6-trinitroaniline by multiplying 2/3