Picramic acid
| Names | |
|---|---|
| IUPAC name
2-Amino-4,6-dinitrophenol
| |
| Other names
1-Amino-2-hydroxy-3,5-dinitrobenzene
1-Hydroxy-2-amino-4,6-dinitrobenzene 2-Amino-4,6-dinitro-1-hydroxybenzene 2-Amino-4,6-DNP 4,6-dinitro-2-aminophenol | |
| Properties | |
| C6H5N3O5 | |
| Molar mass | 199.12 g/mol |
| Appearance | Brown solid |
| Density | 1.749 g/cm3 |
| Melting point | 169 °C (336 °F; 442 K) |
| Boiling point | 386.3 °C (727.3 °F; 659.5 K) |
| 0.14 g/100 ml (22 °C)[1] | |
| Solubility | Soluble in acetic acid, benzene, ethanol Slightly soluble in diethyl ether |
| Hazards | |
| Related compounds | |
| Related compounds
|
Picric acid |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Picramic acid, also known as 2-amino-4,6-dinitrophenol, is an organic explosive and toxic compound.
Contents
Properties
Chemical
Picramic acid will decompose at high temperatures.
Physical
Picramic acid is a reddish-brown solid, slightly soluble in water, but more soluble in organic solvents.
Availability
Some types of henna dye contain sodium picramate, which can be acidified to picramic acid.
Preparation
Picramic acid can be obtained by neutralizing an alcoholic solution of picric acid with aq. ammonia, followed by hydrogen sulfide.[2]
Sodium sulfide can also be used. The reaction product is the sodium salt of picramic acid, which can be converted to free acid by the addition of a mineral acid.[3][4][5]
Another route involves the nitration of 2-amino-2-nitrophenol with nitrating mixture, at 0-5 °C. Yield is given as 40%.[6]
Projects
- Energetic compound
- Make henna
Handling
Safety
Picramic acid is explosive and harmful. Handle it with care.
Storage
In closed bottles.
Disposal
Like all aromatics, it can be safely neutralized with an oxidizing solution, like Fenton's reagent, though other means exist.
References
- ↑ Dabney; American Chemical Journal; vol. 5; (1883); p. 36,
- ↑ Lea; Chem. News J. Ind. Sci.; vol. 4; (1861); p. 637,193
- ↑ sodium picramate preparation
- ↑ Sodium Picramate
- ↑ Korenman et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 50; (1977); p. 685,655
- ↑ Gorelik; Shteiman; Shner; Romanskii; Kuznetsova; Russian Journal of Organic Chemistry; vol. 33; nb. 3; (1997); p. 348 - 352
