Picramic acid
Names
Preferred IUPAC name
2-Amino-4,6-dinitrophenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.314 Edit this at Wikidata
EC Number
  • 202-544-6
UNII
UN number 3317
  • InChI=1S/C6H5N3O5/c7-4-1-3(8(11)12)2-5(6(4)10)9(13)14/h1-2,10H,7H2 checkY
    Key: QXYMVUZOGFVPGH-UHFFFAOYSA-N checkY
  • InChI=1S/C6H5N3O5/c7-4-1-3(8(11)12)2-5(6(4)10)9(13)14/h1-2,10H,7H2
  • c1c(cc(c(c1N)O)[N+](=O)[O-])[N+](=O)[O-]
Properties
C6H5N3O5
Molar mass 199.12 g/mol
Appearance Brown paste
Density 1.749 g/cm3
Melting point 169 °C (336 °F; 442 K)
Boiling point 386.3 °C (727.3 °F; 659.5 K)
log P 2.41840[1]
1.73 [1]
Hazards
GHS labelling:[2]
GHS01: ExplosiveGHS07: Exclamation mark
Danger
H201, H302, H312, H332, H412
P210, P230, P240, P250, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P370+P380, P372, P373, P401, P501
Flash point 187.5 °C (369.5 °F; 460.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Picramic acid, also known as 2-amino-4,6-dinitrophenol,[3] is an acid obtained by neutralizing an alcoholic solution of picric acid with ammonium hydroxide. Hydrogen sulfide is then added to the resulting solution, which turns red, yielding sulfur and red crystals. These are the ammonium salts of picramic acid, from which it can be extracted using acetic acid.[4] Picramic acid is explosive and very toxic. It has a bitter taste.[5]

Along with its sodium salt (sodium picramate) it is used in low concentrations in certain hair dyes, such as henna, it is considered safe for this use provided its concentration remains low.[6]

References

  1. ^ a b "Picramic acid". www.chemsrc.com. Archived from the original on 2020-06-06. Retrieved 2019-04-05.
  2. ^ "2-Amino-4,6-dinitrophenol". pubchem.ncbi.nlm.nih.gov. Retrieved 27 December 2021.
  3. ^ "Haz-Map Category Details". Archived from the original on 2018-09-20. Retrieved 2014-04-09.
  4. ^ "Archived copy" (PDF). Archived (PDF) from the original on 2020-06-06. Retrieved 2014-04-09.((cite web)): CS1 maint: archived copy as title (link)
  5. ^ "PICRAMIC ACID (2-AMINO-4,6-DINITROPHENOL)". Archived from the original on 2011-08-29. Retrieved 2011-04-30.
  6. ^ "Final Report on the Safety Assessment of Sodium Picramate". Journal of the American College of Toxicology. 11 (4): 447–464. July 1992. doi:10.3109/10915819209141884. S2CID 208504486.
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