2,4-Dinitroaniline

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[1][2]

The ball-and-stick structure of 2,4-dinitroaniline

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
EC Number
  • 202-553-5
KEGG
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
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:
GHS01: Explosive GHS02: Flammable GHS06: Toxic GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
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)
NFPA 704 four-colored 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).
Infobox references

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

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

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