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{{Chembox
{{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 =
| IUPACName = 2-amino-4,6-dinitrophenol
| SystematicName = 2-amino-4,6-dinitrophenol
| PIN = 2-Amino-4,6-dinitrophenol
| OtherNames =
| SystematicName =
| OtherNames =
⚫
|Section1={{Chembox Identifiers
| IUPACName =
⚫
| Section1 = {{Chembox Identifiers
| Abbreviations =
| Abbreviations =
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 96-91-3
| CASNo = 96-91-3
| EINECS = 202-544-6
| ChEMBL = 3183248
⚫
| PubChem = 4921319
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4103087
| ChemSpiderID = 4103087
| EINECS = 202-544-6
⚫
| PubChem = 4921319
| UNNumber = 3317
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5VDQ7GK8L3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QXYMVUZOGFVPGH-UHFFFAOYSA-N
| 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-]
| 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 =
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| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
| ATCCode_prefix =
| ATCCode_suffix =
| ATC_Supplemental =
⚫
}}
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|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>5</sub>N<sub>3</sub>O<sub>5</sub>
| Formula = C<sub>6</sub>H<sub>5</sub>N<sub>3</sub>O<sub>5</sub>
| MolarMass = 199.12 g/mol
| MolarMass = 199.12 g/mol
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| SolubleOther =
| SolubleOther =
| Solvent =
| 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 =
| VaporPressure =
| HenryConstant =
| HenryConstant =
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| pKb =
| pKb =
}}
}}
|Section3={{Chembox Structure
| Section3 = {{Chembox Structure
| CrystalStruct =
| CrystalStruct =
| Coordination =
| Coordination =
| MolShape =
| MolShape =
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}}
|Section4={{Chembox Thermochemistry
| Section4 = {{Chembox Thermochemistry
| DeltaHf =
| DeltaHf =
| DeltaHc =
| DeltaHc =
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| HeatCapacity =
| HeatCapacity =
}}
}}
|Section5={{Chembox Pharmacology
| Section6 = {{Chembox Explosive
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| PregCat =
| PregCat_AU =
| PregCat_US =
}}
|Section6={{Chembox Explosive
| ShockSens =
| ShockSens =
| FrictionSens =
| FrictionSens =
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| REFactor =
| REFactor =
}}
}}
|Section7={{Chembox Hazards
| Section7 = {{Chembox Hazards
| ExternalSDS =
| ExternalSDS =
| EUClass =
| MainHazards =
| MainHazards =
| NFPA-H =
| NFPA-H =
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| NFPA-R =
| NFPA-R =
| NFPA-S =
| 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
| FlashPtC = 187.5
| AutoignitionPtC =
| AutoignitionPtC =
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| PEL =
| PEL =
}}
}}
|Section8={{Chembox Related
| Section8 = {{Chembox Related
| OtherAnions =
| OtherAnions =
| OtherCations =
| OtherCations =
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}}
}}
}}
}}
'''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 ==
== References ==
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[[Category:Acids]]
[[Category:Acids]]
[[Category:Explosives]]
[[Category:Explosive chemicals]]
[[Category:Phenols]]
[[Category:Dinitrophenol derivatives]]
[[Category:Nitrobenzenes]]
[[Category:Anilines]]
[[Category:Anilines]]

Latest revision as of 22:08, 30 January 2024

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).
checkY verify (what is checkY☒N ?)

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

[edit]
  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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