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Resorcinol (or resorcin) is a Phenols compound. It is an organic compound with the formula C6H4(OH)2. It is one of three , the 1,3-isomer (or meta-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.
Many additional routes exist for resorcinol. It was formerly produced by disulfonation of benzene followed by hydrolysis of the 1,3-disulfonate. This method has been discarded because it cogenerates so much sulfur-containing waste. Resorcinol can also be produced when any of a large number of (such as galbanum and asafoetida) are melted with potassium hydroxide, or by the distillation of Brazilwood extract. It may be synthesized by melting 3-iodophenol, phenol-3-sulfonic acid with potassium carbonate. Diazotization of 3-aminophenol or on 1,3-diaminobenzene followed by hydrolysis provides yet another route. Many ortho- and para-compounds of the aromatic series (for example, the bromophenols, benzene- para-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide.
It reduces Fehling's solution and ammoniacal silver solutions. It does not form a precipitate with lead acetate solution, as does the isomeric pyrocatechol. Iron(III) chloride colors its aqueous solution a dark-violet, and bromine water precipitates tribromoresorcinol. These properties are what give it its use as a colouring agent for certain chromatography experiments.
Sodium amalgam reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated barium hydroxide solution gives γ-acetylbutyric acid.
When fused with potassium hydroxide, resorcinol yields phloroglucin, pyrocatechol, and diresorcinol. It condenses with or , in the presence of dehydrating agents, to oxyketones, for example, with zinc chloride and glacial acetic acid at 145 °C it yields resacetophenone (HO)2C6H3COCH3. With the of dibasic acids, it yields . When heated with calcium chloride—ammonia to 200 °C it yields meta-dioxydiphenylamine.A. Seyewitz, Bull. Soc. Chins., 1890, 3, p. 811
With sodium nitrite it forms a water-soluble blue dye, which is turned red by acids, and is used as a pH indicator under the name of lacmoid. It condenses readily with , yielding with formaldehyde, on the addition of catalytic hydrochloric acid, methylene diresorcin (HO)C6H3(O)2CH2. Reaction with chloral hydrate in the presence of potassium bisulfate yields the lactone of tetra-oxydiphenyl methane carboxylic acid.J. T. Hewitt and F. G. Pope, Jour. C/tern. Soc., 1897, 75, p. 1084 In alcoholic solution it condenses with sodium acetoacetate to form 4-methylumbelliferone.
In addition to electrophilic aromatic addition, resorcinol (and other ) undergo nucleophilic substitution via the enone tautomer.
Nitration with concentrated nitric acid in the presence of cold concentrated sulfuric acid yields trinitroresorcin (styphnic acid), an explosive.
In the 1950s and early 1960s the British Army used it, in the form of a paste applied directly to the skin. One such place where this treatment was given to soldiers with chronic acne was the Cambridge Military Hospital, Aldershot, England. It was not always successful.
A resorcinol derivative, Hexylresorcinol, is an anesthetic found in throat lozenges.
It is an analytical reagent for the qualitative determination of (Seliwanoff's test).
It is the starting material for the initiating explosive lead styphnate."Military Explosives," Department of the Army Technical Manual, TM-9-1300-214 (Washington, D.C.: Department of the Army, September 1984), p. 7-12.
Thioresorcinol is obtained by the action of zinc and hydrochloric acid on meta-benzenedisulfonyl chloride. It melts at 27 °C and boils at 243 °C. Resorcinol disulfonic acid, (HO)2C6H2(HSO3)2, is a Deliquescence mass obtained by the action of sulfuric acid on resorcin. It is readily soluble in water and ethanol.
Resorcinol is also a common scaffold that is found in a class of anticancer agents, some of which (luminespib, ganetespib, KW-2478, and onalespib) were in clinical trials . Part of the resorcinol structure binds to inhibits the N-terminal domain of heat shock protein 90, which is a drug target for anticancer treatments.
Benzene-1,3-diol is the name recommended by the International Union of Pure and Applied Chemistry (IUPAC) in its 1993 Recommendations for the Nomenclature of Organic Chemistry.
Resorcinol is so named because of its derivation from ammoniated resin gum, and for its relation to the chemical orcinol.H. Hlasiwetz and L. Barth (1864) "Ueber einen neuen, dem Orcin homologen Körper" (On a new substance homologous to orcin), Annalen der Chemie, 130 (3) : 354-359. Resorcinol is named on p. 358: "Wir nennen den neuen Körper, da wir gefunden haben, dass er auch aus dem Ammoniakgummiharz erhalten werden kann, Resorcin , um an seine Entstehung aus Harzen und seine Beziehung zum Orcin zu erinnern." (We name the new substance, since we have found that it can be obtained from ammoniated resin gum, resorcin, in order to recall its creation from resin and its relation to orcinol.)
Resorcinol was named a substance of very high concern under European Union REACH in 2022 because of its endocrine disrupting properties.
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