Picramic acid

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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.

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

  1. Dabney; American Chemical Journal; vol. 5; (1883); p. 36,
  2. Lea; Chem. News J. Ind. Sci.; vol. 4; (1861); p. 637,193
  3. sodium picramate preparation
  4. Sodium Picramate
  5. Korenman et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 50; (1977); p. 685,655
  6. Gorelik; Shteiman; Shner; Romanskii; Kuznetsova; Russian Journal of Organic Chemistry; vol. 33; nb. 3; (1997); p. 348 - 352

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