2,4-Dinitroaniline

2,4-Dinitroaniline is a chemical compound with a formula of C₆H₅N₃O₄. It is used as an intermediate in the manufacturing and production of pesticides, herbicides, pharmaceuticals, and dyes ^[3]. It is not classified as an explosive like other nitroaromatics.

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
CAS Number	97-02-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34242
ChEMBL	ChEMBL354318
ChemSpider	7045
ECHA InfoCard	100.002.322
EC Number	202-553-5
KEGG	C14713
PubChem CID	7321
RTECS number	BX9100000
UNII	5BI780R6W6
UN number	1596
CompTox Dashboard (EPA)	DTXSID1021823
InChI InChI=1S/C6H5N3O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H,7H2 Key: LXQOQPGNCGEELI-UHFFFAOYSA-N
SMILES C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])N
Properties
Chemical formula	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
Solubility in water	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
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Toxic, Health and Environmental hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H373, H411
Precautionary statements	P260, P262, P264, P270, P271, P273, P280, P284, P301+P310+P330, P302+P350, P304+P340+P310, P314, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	3 1 3
Flash point	224 °C (435 °F; 497 K)
Autoignition temperature	350
Lethal dose or concentration (LD, LC):
LD50 (median dose)	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 pK_a of conjugate acid of 2,4-dinitroaniline being even lower than that of hydronium ions, meaning that it is a strong acid.

C₆H₃(NH+3)(NO₂)₂ + H₂O → C₆H₃(NH₂)(NO₂)₂ + H₃O⁺

The protons in the amino group is also much more acidic than that of aniline.

Uses

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 toxic, with a lethal dose of 285 mg/kg. It is also reported to penetrate through skin leading to acute dermal toxicity ratings ^[4].

See also

• 2,4,6-Trinitroaniline
• 4-Nitroaniline