Picramic acid

Picramic acid
Names
	Preferred IUPAC name 2-Amino-4,6-dinitrophenol
Identifiers
CAS Number	96-91-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3183248;
ChemSpider	4103087 ;
ECHA InfoCard	100.002.314
EC Number	202-544-6;
PubChem CID	4921319;
UNII	5VDQ7GK8L3 ;
UN number	3317
CompTox Dashboard (EPA)	DTXSID5024479 ;
	InChI InChI=1S/C6H5N3O5/c7-4-1-3(8(11)12)2-5(6(4)10)9(13)14/h1-2,10H,7H2 Key: QXYMVUZOGFVPGH-UHFFFAOYSA-N ; InChI=1S/C6H5N3O5/c7-4-1-3(8(11)12)2-5(6(4)10)9(13)14/h1-2,10H,7H2;
	SMILES c1c(cc(c(c1N)O)[N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	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
Refractive index (nD)	1.73
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H201, H302, H312, H332, H412
Precautionary statements	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). verify (what is ?) Infobox references

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

^ ^a ^b "Picramic acid". www.chemsrc.com. Archived from the original on 2020-06-06. Retrieved 2019-04-05.
^ "2-Amino-4,6-dinitrophenol". pubchem.ncbi.nlm.nih.gov. Retrieved 27 December 2021.
^ "Archived copy". Archived from the original on 2018-09-20. Retrieved 2014-04-09.{{cite web}}: CS1 maint: archived copy as title (link)
^ "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)
^ "PICRAMIC ACID (2-AMINO-4,6-DINITROPHENOL)". Archived from the original on 2011-08-29. Retrieved 2011-04-30.
^ "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.

[chemsrc-1] "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] "Archived copy". Archived from the original on 2018-09-20. Retrieved 2014-04-09.{{cite web}}: CS1 maint: archived copy as title (link)

[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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