Names | |
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Preferred IUPAC name 2-(Hydroxymethyl)phenol | |
Other names 2-Hydroxybenzyl alcohol, Salicain, Diathesin, Saligenin, Saligenol, Salicyl alcohol, α,2-Toluenediol, o-Methylolphenol, 2-Methylolphenol, Salicylic alcohol [1] | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.001.782 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C7H8O2 | |
Molar mass | 124.139 g·mol−1 |
Density | 1.16 g/cm3 |
Melting point | 86 °C (187 °F; 359 K) |
Boiling point | 267 °C (513 °F; 540 K) |
67g/L at 22 °C [2] | |
-76.9·10−6 cm3/mol | |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Flash point | 134 °C [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Salicyl alcohol (saligenin) is an organic compound with the formula C6HOH(CH2OH. It is a white solid that is used as a precursor in organic synthesis. [3]
Salicyl alcohol is produced by the hydroxymethylation of phenol using formaldehyde: [4]
Air oxidation of salicyl alcohol gives salicylaldehyde.
Chemical sweeteners are formed by acetal formation with e.g. isovanillin (Cmp4). [5]
Salicyl alcohol appears as a pharmacophore in several notable β2-adrenoceptor agonists (e.g. salbutamol), as well as in synthetic estrone analogs, e.g. CID:22940780 or CID:154236944.
Salicyl alcohol is the precursor of salicylic acid. [6] It is formed from salicin by enzymatic hydrolysis by Salicyl-alcohol beta-D-glucosyltransferase or by acid hydrolysis.
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sucrose and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.
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.
Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula C4H4NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.
Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.
Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF3)2CHOH. This fluoroalcohol finds use as solvent in organic chemistry. Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index. It is a colorless, volatile liquid with a pungent odor.
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.
In organic chemistry a halohydrin is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups. The term only applies to saturated motifs, as such compounds like 2-chlorophenol would not normally be considered halohydrins. Megatons of some chlorohydrins, e.g. propylene chlorohydrin, are produced annually as precursors to polymers.
Glutaric acid is the organic compound with the formula C3H6(COOH)2. Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w).
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a precursor to coumarin and a variety of chelating agents.
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.
Lithium borohydride (LiBH4) is a borohydride and known in organic synthesis as a reducing agent for esters. Although less common than the related sodium borohydride, the lithium salt offers some advantages, being a stronger reducing agent and highly soluble in ethers, whilst remaining safer to handle than lithium aluminium hydride.
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.
Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.
Cyclohexenone is an organic compound which is a versatile intermediate used in the synthesis of a variety of chemical products such as pharmaceuticals and fragrances. It is colorless liquid, but commercial samples are often yellow.
Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. The cation P(CH2OH)4+ is four-coordinate, as is typical for phosphonium salts. THPC has applications as a precursor to fire-retardant materials, as well as a microbiocide in commercial and industrial water systems.
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.
Methylphosphonyl dichloride (DC) or dichloro is an organophosphorus compound. It has a number of commercial uses but is most notable as being a precursor to several chemical weapons agents. It is a white crystalline solid that melts slightly above room temperature.
N-Hydroxyphthalimide is the N-hydroxy derivative of phthalimide. The compound can be utilized as a catalyst for oxidation reactions, in particular for the selective oxidation with molecular oxygen under mild conditions.
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