Picramic acid: Difference between revisions

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

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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

^ ^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.
^ "Haz-Map Category Details". Archived from the original on 2018-09-20. Retrieved 2014-04-09.
^ "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] "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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@@ Line 1: / Line 1: @@
 {{Chembox
-| Watchedfields = changed
+| Watchedfields  = changed
-| verifiedrevid = 450797737
+| verifiedrevid  = 450797737
-| Name =
+| Name           =
-| ImageFile =Picramic acid.svg
+| ImageFile      = Picramic acid.svg
+| ImageFile1     = Picramic acid.jpg
-| ImageSize =
+| ImageSize      =
-| PIN = 2-Amino-4,6-dinitrophenol
+| PIN            = 2-Amino-4,6-dinitrophenol
-| OtherNames =
+| SystematicName =
-|Section1={{Chembox Identifiers
+| OtherNames     =
+| IUPACName      =
+| Section1       = {{Chembox Identifiers
 | Abbreviations =
 | CASNo_Ref = {{cascite|correct|??}}
 | CASNo = 96-91-3
-| EINECS = 202-544-6
+| ChEMBL = 3183248
-| PubChem = 4921319
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 4103087
+| EINECS = 202-544-6
+| PubChem = 4921319
+| UNNumber = 3317
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 5VDQ7GK8L3
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C6H5N3O5/c7-4-1-3(8(11)12)2-5(6(4)10)9(13)14/h1-2,10H,7H2
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = 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-]
+ }}
-| InChI = 1S/C6H5N3O5/c7-4-1-3(8(11)12)2-5(6(4)10)9(13)14/h1-2,10H,7H2
+| Section2       = {{Chembox Properties
-| RTECS =
-| MeSHName =
-| ChEBI_Ref = {{ebicite|correct|EBI}}
-| ChEBI =
-| KEGG_Ref = {{keggcite|correct|kegg}}
-| KEGG =
-}}
-|Section2={{Chembox Properties
 | Formula = C<sub>6</sub>H<sub>5</sub>N<sub>3</sub>O<sub>5</sub>
 | MolarMass = 199.12 g/mol
@@ Line 40: / Line 41: @@
 | SolubleOther =
 | Solvent =
+| LogP =  2.41840<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/96-91-3_670346.html|title=Picramic acid|website=www.chemsrc.com|access-date=2019-04-05|archive-date=2020-06-06|archive-url=https://web.archive.org/web/20200606155054/https://www.chemsrc.com/en/cas/96-91-3_670346.html|url-status=live}}</ref>
-| LogP =
+| RefractIndex = 1.73 <ref name="chemsrc"/>
 | VaporPressure =
 | HenryConstant =
@@ Line 47: / Line 49: @@
 | pKb =
   }}
-|Section3={{Chembox Structure
+| Section3       = {{Chembox Structure
 | CrystalStruct =
 | Coordination =
 | MolShape =
   }}
-|Section4={{Chembox Thermochemistry
+| Section4       = {{Chembox Thermochemistry
 | DeltaHf =
 | DeltaHc =
@@ Line 58: / Line 60: @@
 | HeatCapacity =
   }}
-|Section5={{Chembox Pharmacology
+| Section6       = {{Chembox Explosive
-| AdminRoutes =
-| Bioavail =
-| Metabolism =
-| HalfLife =
-| ProteinBound =
-| Excretion =
-| Legal_status =
-| Legal_US =
-| Legal_UK =
-| Legal_AU =
-| Legal_CA =
-| Pregnancy_category =
-| Pregnancy_AU =
-| Pregnancy_US =
-  }}
-|Section6={{Chembox Explosive
 | ShockSens =
 | FrictionSens =
@@ Line 80: / Line 66: @@
 | REFactor =
   }}
-|Section7={{Chembox Hazards
+| Section7       = {{Chembox Hazards
 | ExternalSDS =
-| EUClass =
 | MainHazards =
 | NFPA-H =
@@ Line 88: / Line 73: @@
 | NFPA-R =
 | NFPA-S =
+| GHS_ref=<ref>{{cite web |title=2-Amino-4,6-dinitrophenol |url=https://pubchem.ncbi.nlm.nih.gov/compound/4921319#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=27 December 2021 |language=en}}</ref>
-| RPhrases = 2, 4, 23/24/25
+| GHSPictograms = {{GHS01}}{{GHS07}}
-| SPhrases = 28, 35, 37, 45
-| RSPhrases =
+| GHSSignalWord = Danger
+| HPhrases = {{H-phrases|201|302|312|332|412}}
+| PPhrases = {{P-phrases|210|230|240|250|261|264|270|271|273|280|301+312|302+352|304+312|304+340|312|322|330|363|370+380|372|373|401|501}}
 | FlashPtC = 187.5
 | AutoignitionPtC =
@@ Line 97: / Line 84: @@
 | PEL =
   }}
-|Section8={{Chembox Related
+| Section8       = {{Chembox Related
 | OtherAnions =
 | OtherCations =
@@ Line 105: / Line 92: @@
  }}
 }}
-'''Picramic acid''', also known as '''2-amino-4,6-dinitrophenol''',<ref>http://hazmap.nlm.nih.gov/category-details?id=3267&table=copytblagents</ref> 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]].<ref>http://www.jbc.org/content/35/3/565.full.pdf</ref>
+'''Picramic acid''', also known as '''2-amino-4,6-dinitrophenol''',<ref>{{Cite web |url=http://hazmap.nlm.nih.gov/category-details?id=3267&table=copytblagents |title=Haz-Map Category Details |access-date=2014-04-09 |archive-date=2018-09-20 |archive-url=https://web.archive.org/web/20180920101438/https://hazmap.nlm.nih.gov/category-details?id=3267&table=copytblagents |url-status=live }}</ref> 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]].<ref>{{Cite web |url=http://www.jbc.org/content/35/3/565.full.pdf |title=Archived copy |access-date=2014-04-09 |archive-date=2020-06-06 |archive-url=https://web.archive.org/web/20200606155102/https://www.jbc.org/content/35/3/565.full.pdf |url-status=live }}</ref> Picramic acid is [[explosive]] and very [[toxic]]. It has a [[Bitterness (taste)|bitter]] taste.<ref>{{Cite web|url=http://chemicalland21.com/specialtychem/perchem/PICRAMIC%20ACID.htm|title=PICRAMIC ACID (2-AMINO-4,6-DINITROPHENOL)|access-date=2011-04-30|archive-date=2011-08-29|archive-url=https://web.archive.org/web/20110829044602/http://www.chemicalland21.com/specialtychem/perchem/PICRAMIC%20ACID.htm|url-status=live}}</ref>
+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.<ref>{{cite journal |title=Final Report on the Safety Assessment of Sodium Picramate |journal=Journal of the American College of Toxicology |date=July 1992 |volume=11 |issue=4 |pages=447–464 |doi=10.3109/10915819209141884|s2cid=208504486 |doi-access=free }}</ref>
-Picramic acid is [[explosive]] and very [[toxic]]. It has a [[Bitterness (taste)|bitter]] taste.<ref>http://chemicalland21.com/specialtychem/perchem/PICRAMIC%20ACID.htm</ref>
 == References ==
@@ Line 114: / Line 101: @@
 [[Category:Acids]]
 [[Category:Explosive chemicals]]
-[[Category:Nitrophenols]]
+[[Category:Dinitrophenol derivatives]]
 [[Category:Anilines]]