Names | |
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Preferred IUPAC name Phenyl 2-hydroxybenzoate | |
Other names Salol | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.873 |
EC Number |
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KEGG | |
MeSH | C026041 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C13H10O3 | |
Molar mass | 214.22 g/mol |
Appearance | White solid |
Density | 1.25 g/cm3 |
Melting point | 41.5 °C (106.7 °F; 314.6 K) |
Boiling point | 173 °C (343 °F; 446 K) at 12 mmHg |
1 g/6670 mL | |
-123.2·10−6 cm3/mol | |
Refractive index (nD) | 1.615 [2] |
Pharmacology | |
G04BX12 ( WHO ) | |
Hazards | |
Flash point | 137.3 [2] °C (279.1 °F; 410.4 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Phenyl salicylate, or salol, is the organic compound with the formula C6H5O2C6H4OH. It is a white solid. It is occasionally used in sunscreens and as an antiseptic. [3]
The title compound was synthesized first in 1883 by the Polish chemist and doctor Marceli Nencki (who didn't publish his findings) and then independently in 1885 by the German chemist Richard Seifert (de) (1861–1919) (who did publish his findings). It is synthesized by heating salicylic acid with phenol in the presence of phosphoryl chloride. [4] It also arises from heating salicylic acid: [5]
The conversion entails dehydration and decarboxylation. Heating phenyl salicylate in turn gives xanthone. [6] [3]
In this conversion, phenol is produced as well as carbon dioxide.
In the salol reaction, phenyl salicylate reacts with o-toluidine in 1,2,4-trichlorobenzene at elevated temperatures to the corresponding amide o-salicylotoluide. [7] Salicylamides are a type of drug.
It has been used as an antiseptic [8] based on the antibacterial activity upon hydrolysis in the small intestine. [9]
The Swiss physician Hermann Sahli (sometimes spelled "Saly") (1856–1933) sought a substitute for sodium salicylate, which was used as a treatment for rheumatoid arthritis but which wasn't tolerated by some patients. So Dr. Sahli asked the Polish chemist and doctor Marceli Nencki of Bern, Switzerland, if he knew of a salicylate compound that lacked sodium salicylate's side effects. [11] Nencki recommended phenyl salicylate, which he had synthesized circa 1883. [12] [13] While Nencki had been investigating how phenyl salicylate behaved in the body, he hadn't published his findings. [14] Meanwhile, the German chemist Richard Seifert (de) (1861–1919), a student of the German chemist Rudolf Wilhelm Schmitt (de) (1830–1898), [15] independently synthesized phenyl salicylate in 1885. [16] In 1885, Seifert accepted a position at the Heyden chemical corporation (de) of Radebeul, Germany, which manufactured salicylic acid. [17] The United States granted to Nencki and Seifert a patent for the production of phenyl salicylate, [18] whereas Germany granted a patent for its production to Nencki and the Heyden corporation. [19] The Heyden company subsequently sold phenyl salicylate as a pharmaceutical, under the commercial name "Salol", [20] a contraction of "SALicylate of phenOL". [21] Among other applications, [22] Salol was used as an orally administered antiseptic for the small intestine, where the compound is hydrolyzed into salicylic acid and phenol. [18]
Phenyl salicylate is used in school laboratory demonstrations on how cooling rates affect crystal size in igneous rocks, and can be used to demonstrate seed crystal selectiveness.
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6H
5OH. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.
Phenol, or Benzenol, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.
Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.
A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.
Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C8H8O3. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer (in which it is used as a flavoring), but often associatively called "minty", as it is an ingredient in mint candies. It is produced by many species of plants, particularly wintergreens. It is also produced synthetically, used as a fragrance and as a flavoring agent.
Johann Friedrich Wilhelm Adolf von Baeyer was a German chemist who synthesised indigo and developed a nomenclature for cyclic compounds. He was ennobled in the Kingdom of Bavaria in 1885 and was the 1905 recipient of the Nobel Prize in Chemistry.
The Kolbe–Schmitt reaction or Kolbe process is a carboxylation chemical reaction that proceeds by treating phenol with sodium hydroxide to form sodium phenoxide, then heating sodium phenoxide with carbon dioxide under pressure, then treating the product with sulfuric acid. The final product is an aromatic hydroxy acid which is also known as salicylic acid.
Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was first synthesised by Adolf von Baeyer.
Hippuric acid is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenolic compounds. The phenols are first converted to benzoic acid, and then to hippuric acid and excreted in urine.
Wilhelm Marceli Nencki was a Polish chemist and medical doctor who lived in Congress Poland and other parts of the Russian Empire.
This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 C.F.R. 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.
Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenolate and carbon dioxide under higher temperature and pressure. Historically, it has been synthesized by refluxing methyl salicylate with an excess of sodium hydroxide.
Sodium phenoxide (sodium phenolate) is an organic compound with the formula NaOC6H5. It is a white crystalline solid. Its anion, phenoxide, also known as phenolate, is the conjugate base of phenol. It is used as a precursor to many other organic compounds, such as aryl ethers.
The Great Phenol Plot was a clandestine effort by the German Government during the early years of World War I to divert American-produced phenol away from the manufacture of high explosives that supported the British war effort. It was used by the German-owned Bayer company, who could no longer import phenol from Britain, to produce aspirin.
Aspirin is a novel organic compound that does not occur in nature, and was first successfully synthesised in 1899. In 1897, scientists at the drug and dye firm Bayer began investigating acetylated organic compounds as possible new medicines, following the success of acetanilide ten years earlier. By 1899, Bayer created acetylsalicylic acid and named the drug 'Aspirin', going on to sell it around the world. The word Aspirin was Bayer's brand name, rather than the generic name of the drug; however, Bayer's rights to the trademark were lost or sold in many countries. Aspirin's popularity grew over the first half of the twentieth century, leading to fierce competition with the proliferation of aspirin brands and products.
Richard Gustav Müller was a German chemist. He and Eugene G. Rochow independently discovered the direct process of organosilicon compounds in 1941. That synthesis, also known as the Müller-Rochow process is the copper-catalysed reaction of chloromethane with silicon. Müller was awarded the National Prize of East Germany in 1952 for his work.
Triphenylborane, often abbreviated to BPh3 where Ph is the phenyl group C6H5-, is a chemical compound with the formula B(C6H5)3. It is a white crystalline solid and is both air and moisture sensitive, slowly forming benzene and triphenylboroxine. It is soluble in aromatic solvents.
Dimethylcarbamoyl chloride (DMCC) is a reagent for transferring a dimethylcarbamoyl group to alcoholic or phenolic hydroxyl groups forming dimethyl carbamates, usually having pharmacological or pesticidal activities. Because of its high toxicity and its carcinogenic properties shown in animal experiments and presumably also in humans, dimethylcarbamoyl chloride can only be used under stringent safety precautions.
3-Dimethylaminoacrolein is an organic compound with the formula Me2NC(H)=CHCHO. It is a pale yellow water-soluble liquid. The compound has a number of useful and unusual properties, e.g. it "causes a reversal of the hypnotic effect of morphine in mice" and has a "stimulating effect in humans".