Picramic acid

Last updated
Picramic acid
Picramic acid.svg
Picramic acid.jpg
Names
Preferred IUPAC name
2-Amino-4,6-dinitrophenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.314 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-544-6
PubChem CID
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 Yes check.svgY
    Key: QXYMVUZOGFVPGH-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceBrown 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]
GHS-pictogram-explos.svg GHS-pictogram-exclam.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Related Research Articles

<span class="mw-page-title-main">Ammonia</span> Chemical compound

Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the formula NH3. A stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous waste, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to fertilisers. Around 70% of ammonia produced industrially is used to make fertilisers in various forms and composition, such as urea and diammonium phosphate. Ammonia in pure form is also applied directly into the soil.

<span class="mw-page-title-main">Chlorine</span> Chemical element, symbol Cl and atomic number 17

Chlorine is a chemical element; it has symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

<span class="mw-page-title-main">Lithium carbonate</span> Chemical compound

Lithium carbonate is an inorganic compound, the lithium salt of carbonic acid with the formula Li
2
CO
3
. This white salt is widely used in processing metal oxides. It is on the World Health Organization's List of Essential Medicines for its efficacy in the treatment of mood disorders such as bipolar disorder.

<span class="mw-page-title-main">Nitrogen</span> Chemical element, symbol N and atomic number 7

Nitrogen is a chemical element; it has symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element bond to form N2, a colorless and odorless diatomic gas. N2 forms about 78% of Earth's atmosphere, making it the most abundant uncombined element in air. Because of the volatility of nitrogen compounds, nitrogen is relatively rare in the solid parts of the Earth.

Urea, also called carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups joined by a carbonyl functional group. It is thus the simplest amide of carbamic acid.

<span class="mw-page-title-main">Sodium hydroxide</span> Chemical compound with formula NaOH

Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations Na+ and hydroxide anions OH.

<span class="mw-page-title-main">Surfactant</span> Substance that lowers the surface tension between a liquid and another material

Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word "surfactant" is a blend of surface-active agent, coined c. 1950. As they consist of a water-repellent and a water-attracting part, they enable water and oil to mix; they can form foam and facilitate the detachment of dirt.

<span class="mw-page-title-main">Base (chemistry)</span> Type of chemical substance

In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century.

<span class="mw-page-title-main">Sodium carbonate</span> Chemical compound

Sodium carbonate is the inorganic compound with the formula Na2CO3 and its various hydrates. All forms are white, odourless, water-soluble salts that yield alkaline solutions in water. Historically, it was extracted from the ashes of plants grown in sodium-rich soils, and because the ashes of these sodium-rich plants were noticeably different from ashes of wood, sodium carbonate became known as "soda ash". It is produced in large quantities from sodium chloride and limestone by the Solvay process, as well as by carbonating sodium hydroxide which is made using the Chlor-alkali process.

<span class="mw-page-title-main">Flux (metallurgy)</span> Chemical used in metallurgy for cleaning or purifying molten metal

In metallurgy, a flux is a chemical cleaning agent, flowing agent, or purifying agent. Fluxes may have more than one function at a time. They are used in both extractive metallurgy and metal joining.

Classical qualitative inorganic analysis is a method of analytical chemistry which seeks to find the elemental composition of inorganic compounds. It is mainly focused on detecting ions in an aqueous solution, therefore materials in other forms may need to be brought to this state before using standard methods. The solution is then treated with various reagents to test for reactions characteristic of certain ions, which may cause color change, precipitation and other visible changes.

<span class="mw-page-title-main">Ion-exchange resin</span> Organic polymer matrix bearing ion-exchange functional groups

An ion-exchange resin or ion-exchange polymer is a resin or polymer that acts as a medium for ion exchange. It is an insoluble matrix normally in the form of small microbeads, usually white or yellowish, fabricated from an organic polymer substrate. The beads are typically porous, providing a large surface area on and inside them where the trapping of ions occurs along with the accompanying release of other ions, and thus the process is called ion exchange. There are multiple types of ion-exchange resin. Most commercial resins are made of polystyrene sulfonate, followed up by polyacrylate.

<span class="mw-page-title-main">Ammonium sulfate</span> Chemical compound

Ammonium sulfate (American English and international scientific usage; ammonium sulphate in British English); (NH4)2SO4, is an inorganic salt with a number of commercial uses. The most common use is as a soil fertilizer. It contains 21% nitrogen and 24% sulfur.

<span class="mw-page-title-main">Cyanuric acid</span> Chemical compound belonging to the class of triazine

Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleaches, disinfectants, and herbicides. In 1997, worldwide production was 160 000 tonnes.

Acid salts are a class of salts that produce an acidic solution after being dissolved in a solvent. Its formation as a substance has a greater electrical conductivity than that of the pure solvent. An acidic solution formed by acid salt is made during partial neutralization of diprotic or polyprotic acids. A half-neutralization occurs due to the remaining of replaceable hydrogen atoms from the partial dissociation of weak acids that have not been reacted with hydroxide ions to create water molecules.

<span class="mw-page-title-main">Biuret test</span> Chemical test for detecting peptide bonds

In chemistry, the Biuret test, also known as Piotrowski's test, is a chemical test used for detecting the presence of at least two peptide bonds in a molecule. In the presence of peptides, a copper(II) ion forms mauve-colored coordination complexes in an alkaline solution. The reaction was first observed in 1833; In Poland, the biuret test is also known as Piotrowski's test in honor of the Polish physiologist Gustaw Piotrowski who independently rediscovered it in 1857. Several variants on the test have been developed, such as the BCA test and the Modified Lowry test.

The Kjeldahl method or Kjeldahl digestion (Danish pronunciation:[ˈkʰelˌtɛˀl]) in analytical chemistry is a method for the quantitative determination of nitrogen contained in organic substances plus the nitrogen contained in the inorganic compounds ammonia and ammonium (NH3/NH4+). Without modification, other forms of inorganic nitrogen, for instance nitrate, are not included in this measurement. Using an empirical relation between Kjeldahl nitrogen content and protein content it is an important method for analyzing proteins. This method was developed by Johan Kjeldahl in 1883.

<span class="mw-page-title-main">Bleach</span> Chemicals used to whiten or disinfect

Bleach is the generic name for any chemical product that is used industrially or domestically to remove colour (whitening) from fabric or fiber or to disinfect after cleaning. It often refers specifically to a dilute solution of sodium hypochlorite, also called "liquid bleach".

<span class="mw-page-title-main">2,4-Dinitroanisole</span> Chemical compound

2,4-Dinitroanisole (DNAN) is a low sensitivity organic compound. It has an anisole (methoxybenzene) core, with two nitro groups (–NO2) attached.

Potassium hypochlorite is the potassium salt of hypochlorous acid. It is used in variable concentrations, often diluted in water solution. It has a light grey color and a strong chlorine smell. It can be used as a disinfectant.

References

  1. 1 2 "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.