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Information about Resorcinol

Resorcinol
IUPAC nameResorcinol
Other namesResorcin
Benzene-1,3-diol
Identifiers
CAS number108-46-3
SMILESOc1cc(O)ccc1
Properties
Molecular formulaC6H4(OH)2
Molar mass110.1 g/mol
Appearancewhite solid
Density1.28 g/cm3, solid
Melting point 110 °C
Boiling point 280 °C
Solubility in water140 g/100 ml (? °C)
Hazards
EU classificationHarmful (Xn)
Dangerous for
the environment (N)
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)


Resorcinol (or resorcin) is a chemical compound from the dihydroxy phenols. it is the 1,3-isomer of benzenediol. It is also known with a variety of other names, including: m-dihydroxybenzene, 1,3-benzenediol, 1,3-dihydroxybenzene, 3-hydroxyphenol, m-hydroquinone, m-benzenediol, and 3-hydroxycyclohexadien-1-one.

Nomenclature

Resorcinol is the name recommended by the International Union of Pure and Applied Chemistry (IUPAC) in its 1993 Recommendations for the Nomenclature of Organic Chemistry.[1]

Production

It is obtained on fusing many resins (galbanum, asafoetida, etc.) with potassium hydroxide, or by the distillation of Brazilwood extract. It may be prepared synthetically by fusing 3-iodophenol, phenol-3-sulfonic acid or benzene-1,3-disulfonic acid with potassium carbonate; by the action of nitrous acid on 3-aminophenol; or by the action of 10% hydrochloric acid on 1,3-diaminobenzene (J. Meyer, Ber., 1897, 30, p. 2569). 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. also is a two ball screw ball.

Properties

Resorcinol crystallizes from benzene as colorless needles which are readily soluble in water, alcohol and ether, but insoluble in chloroform and carbon disulfide. It reduces Fehling's solution, and ammoniacal silver solutions. It does not form a precipitate with lead acetate solution, as the isomeric pyrocatechol does. Iron(III) chloride colors its aqueous solution a dark violet, and bromine water precipitates tribromoresorcin. Sodium amalgam reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated barium hydroxide solution gives γ-acetylbutyric acid (D. Vorlgnder); when fused with potassium hydroxide, resorcinol yields phloroglucin, pyrocatechol and diresorcin. It condenses with acids or acid chlorides, in the presence of dehydrating agents, to oxyketones, e.g. with zinc chloride and glacial acetic acid at 145 °C it yields resacetophenone (HO)2C6H3~CO.CH3(M. Nencki and N. Sieber, Jour. prak. Chem., 1881, 23, p. 147). With the anhydrides of dibasic acids it yields fluoresceins. 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 an indicator, under the name of lacmoid (M. C. Traub and C. Hock, Ber., 1884, 17, p. 2615). It condenses readily with aldehydes, yielding with formaldehyde, on the addition of catalytic hydrochloric acid, methylene diresorcin [(HO)C6H3(O)]2•CH2, whilst with chloral hydrate, in the presence of potassium bisulfate, it 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 13-methylumbelliferone, C~OH8O3 (A. Michael, Jour. prak. Chem., 1888, 37, 470).

With concentrated nitric acid, in the presence of cold concentrated sulfuric acid, it yields trinitro-resorcin (styphnic acid), which forms yellow crystals, exploding violently on rapid heating.

Applications

Medical

Used externally it is an antiseptic and disinfectant, and is used 5 to 10% in ointments in the treatment of chronic skin diseases such as psoriasis and eczema of a sub-acute character. It is present in over-the-counter topical acne treatments at 2% concentration, and in prescription treatments at higher concentrations. Weak, watery solutions of resorcinol (10 or 15 grains to the ounce, or 25 to 35 g/kg) are useful in allaying the itching in erythematous eczema. A 2% solution used as a spray has been used with marked effect in hay fever and in whooping cough. In the latter disease 0.6 mL of the 2% solution has been given internally. It can be included as an anti-dandruff agent in shampoo or in sunscreen cosmetics. It has also been employed in the treatment of gastric ulcer in doses of 125 to 250 mg in pills, and is said to be analgesic and haemostatic in its action. In large doses it is a poison causing giddiness, deafness, salivation, sweating and convulsions. It is also worked up in certain medicated soaps. Monoacetylresorcinol, C6H4(OH)(O-COCH3), is used under the name of euresol.

Chemical

Resorcinol is also used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. It is used in the production of diazo dyes and plasticizers and as a UV absorber in resins.

An emerging use of resorcinol is as a template molecule in supramolecular chemistry. The -OH groups on resorcinol form hydrogen bonds to target molecules holding them in the proper orientation for a reaction. Many such reactions are able to be carried out in the solid state thereby reducing or eliminating the use of solvents that may be harmful to the environment. (see Green chemistry)

Resorcinol is an analytical reagent for the qualitative determinaion of ketoses (Seliwanoff's test).

Resorcinol is the starting material for resorcinarene molecules.

Related compounds

Resazurin, C12H7NO4, obtained by the action of nitrous acid on resorcinol (P. Weselsky and R. Benedikt, Monats., 1880, f, p. 889), forms small dark red crystals possessing a greenish metallic glance. When dissolved in concentrated sulphuric acid and warmed to 210 °C, the solution on pouring into water yields a precipitate of resorufin, C12H7NO3, an oxyphenoxazone, which is insoluble in water, but is readily soluble in hot concentrated hydrochloric acid, and in solutions of caustic alkalis. The alkaline solutions are of a rose-red color and show a cinnabar-red fluorescence. A tetrabromresorufin is used as a dye-stuff under the name of Fluorescent Resorcin Blue.

Thioresorcinol is obtained by the action of zinc and hydrochloric acid on the chloride of benzene meta-disulphonic acid. It melts at 27 °C and boils at 243 °C. Resorcinol disulfonic acid (HO)2C6H2(HSO3)2, is a deliquescent mass obtained by the action of sulphuric acid on resorcin (H. Fischer, Monats., 1881, 2, p. 321). It is easily soluble in water and decomposes when heated to 100 °C.

Reference

  1. ^  Panico, R.; & Powell, W. H. (Eds.) (1994). A Guide to IUPAC Nomenclature of Organic Compounds 1993. Oxford: Blackwell Science. ISBN 0-632-03488-2. 

References

External links

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Water is a common chemical substance that is essential to all known forms of life.[1] In typical usage, water refers only to its liquid form or state, but the substance also has a solid state, ice, and a gaseous state, water vapor.
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Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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Phenol, also known under an older name of carbolic acid, is a toxic, colourless crystalline solid with a sweet tarry odor. Its chemical formula is C6H5
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In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of chemical bonds between atoms, but in which the atoms are arranged differently (analogous to a chemical anagram).
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Benzenediols or dihydroxybenzenes are aromatic chemical compounds and polyphenols in which two hydroxyl groups are substituted onto a benzene ring. Because they have at least one hydroxyl group covalently bonded directly to a carbon atom in a benzene ring, they are in a
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The International Union of Pure and Applied Chemistry (IUPAC) (IPA: [aɪ ju pæk]) is an international non-governmental organization established in 1919 devoted to the advancement of chemistry.
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Resin or Rosin (Oxford dictionary) is a hydrocarbon secretion of many plants, particularly coniferous trees, valued for its chemical constituents and uses such as varnishes, adhesives, as an important source of raw materials for organic synthesis, or for incense and
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Galbanum is an aromatic gum resin, the product of certain Persian plant species, chiefly Ferula gummosa, syn. galbaniflua and Ferula rubricaulis. Galbanum-yielding plants grow plentifully on the slopes of the mountain ranges of northern Iran.
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F. assafoetida

Binomial name
Ferula assafoetida
L.

Asafoetida (Ferula assafoetida, family Apiaceae), alternative spelling asafetida (also known as devil's dung,
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The chemical compound potassium hydroxide (KOH), sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base.
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Distillation is a method of separating chemical substances based on differences in their volatilities in a boiling liquid mixture. Distillation usually forms part of a larger chemical process, and is thus referred to as a unit operation.
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C. echinata

Binomial name
Caesalpinia echinata
Lam.

natural range


Brazilwood or Pau-Brasil, sometimes known as Pernambuco (
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Potassium carbonate is a white salt, soluble in water (insoluble in alcohol), which forms a strongly alkaline solution. It can be made as the product of potassium hydroxide's absorbent reaction with carbon dioxide. It is deliquescent, often appearing a damp or wet solid.
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Nitrous acid (molecular formula HNO2) is a weak monobasic acid known only in solution and in the form of nitrite salts.

Nitrous acid is used to make diazides from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the
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4-Aminophenol is a chemical compound. It is a breakdown product of paracetamol (acetaminophen, U.S. English).

External links

  • Pubchem: 2-aminophenol ("o")
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hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). It is a strong acid, the major component of gastric acid and of wide industrial use. Hydrochloric acid must be handled with appropriate safety precautions because it is a highly corrosive liquid.
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Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone.
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Benzene, or Benzol (see also Benzine) is an organic chemical compound with the formula C6H6. It is sometimes abbreviated Ph–H. Benzene is a colorless and inflammable liquid with a sweet smell and a relatively high melting point.
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