2,4-Dinitroaniline

2,4-Dinitroaniline[1][2]
	; The ball-and-stick structure of 2,4-dinitroaniline
	; The chemical structure of 2,4-dinitroaniline
Names
	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/cm
Melting point	187.8 °C (370.0 °F; 460.9 K)
Boiling point	Decomposes
Solubility in water	0.06 g/L (20 ºC)
Solubility	Soluble in acetone, ethyl acetate, acetonitrile and most alcohols
Acidity (pKa)	-4.53 (conjugate acid) ; 18.46
Explosive data
Shock sensitivity	Low
Friction sensitivity	Low
Detonation velocity	4,800 m/s
Hazards
Main hazards	Explosive, Toxic, Health and Environmental hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H300, H310, H330, H373, H411
GHS precautionary statements	P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+233, P405, P501
NFPA 704 (fire diamond)	1 3 3
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).
	Infobox references

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.

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.

{\ce {C6H3(NH3+)(NO2)2 + H2O -> C6H3(NH2)(NO2)2 + H3O+}}

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. It is also used for the manufacture of azo dyes and disperse dyes, but also can be used as printing ink, toner and preparation of preservatives. and it is an intermediate for disperse dyes, neutral dyes, sulfur dyes, 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.

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References

"2,4-Dinitroaniline CAS#: 97-02-9". www.chemicalbook.com. Retrieved 2019-03-23.
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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[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]