Resorcinol
IUPAC name	Benzene-1,3-diol
Other names	Resorcin m-dihydroxybenzene; 1,3-benzenediol; 1,3-Dihydroxybenzene; 3-Hydroxyphenol
Identifiers
CAS number	[108-46-3]
SMILES	Oc1cc(O)ccc1
Properties
Molecular formula	C6H4(OH)2
Molar mass	110. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 1 g/mol
Appearance	white solid
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 28 g/cm3, solid
Melting point	110 °C
Boiling point	277 °C
Solubility in water	Very soluble (110 g/100 mL at 20 deg C)
Hazards
EU classification	Harmful (Xn) Dangerous for the environment (N)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Resorcinol (or resorcin) is a chemical compound from the dihydroxy phenols. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 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 In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" it is the 1,3-isomer of benzenediol. This article is about the chemical concept For "isomerism" of atomic nuclei see Nuclear isomer. Benzenediols or dihydroxybenzenes are Aromatic Chemical compounds and Polyphenols in which two Hydroxyl groups are substituted onto a 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.

Contents 1 Nomenclature 2 Production 3 Properties 4 Applications 4.1 Medical 4.2 Chemical 5 Related compounds 6 References 7 External links

Nomenclature

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. The International Union of Pure and Applied Chemistry ( IUPAC) (aɪjuːpæk or ay-yoo-pec) is an international Non-governmental organization ^[1]

Production

It is obtained on fusing many resins (galbanum, asafoetida, etc. Resin, not to be confused with Rosin, is a Hydrocarbon Secretion of many Plants particularly coniferous trees. Galbanum is an aromatic gum Resin, the product of certain Persian plant species chiefly Ferula gummosa'' syn Asafoetida ( Ferula assafoetida) alternative spelling asafetida, æsəˈfɛtɪdə (also known as devil's dung, stinking gum, asant ) with potassium hydroxide, or by the distillation of Brazilwood extract. Potassium hydroxide is the Inorganic compound with the formula K[[hydroxide OH]] Distillation is a method of separating Mixtures based on differences in their volatilities in a boiling liquid mixture Brazilwood or Pau-Brasil, sometimes known as Pernambuco ( Caesalpinia echinata Syn 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 ^[2]. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic Carbonate of potash redirects here For one of potassium carbonate's impure forms see Potash. Nitrous acid (molecular formula H[[Nitrogen N]] O 2 is a weak and monobasic Acid known only in Solution and in the form of Nitrite Hydrochloric acid is the Solution of Hydrogen chloride ( H[[Chlorine Cl]] in water 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.

Properties

Resorcinol crystallizes from benzene as colorless needles which are readily soluble in water, alcohol and ether, but insoluble in chloroform and carbon disulfide. Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 Chloroform, also known as trichloromethane and methyl trichloride, is a Chemical compound with formula C[[Hydrogen H]] Cl It reduces Fehling's solution, and ammoniacal silver solutions. Fehling's solution is a Solution used to differentiate between water soluble Aldehyde and Ketone Functional groups although Ketose Tollens' reagent is usually ammoniacal silver nitrate but can also be other compounds as long as there is an aqueous diamminesilver(I complex. It does not form a precipitate with lead acetate solution, as the isomeric pyrocatechol does. Lead(II acetate is a Chemical compound, a white crystalline substance with a Sweetish taste Pyrocatechol, more commonly known as catechol, is the Organic compound with the formula C6H4(OH2 Iron(III) chloride colors its aqueous solution a dark violet, and bromine water precipitates tribromoresorcin. Iron chloride redirects here For Iron(II chloride see Iron(II chloride. These properties are what give it its use as a colouring agent for certain Chromatography experiments. Chromatography (from Greek χρώμα chroma, color and γραφειν"graphein" to write is the collective term for a family of Laboratory Sodium amalgam reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated barium hydroxide solution gives γ-acetylbutyric acid (D. Sodium amalgam, commonly denoted Na(Hg is an Amalgam, or Alloy of mercury, with Sodium Metal. Barium hydroxide is the Chemical compound with the formula Ba(OH2 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. A condensation reaction is a Chemical reaction in which two Molecules or moieties ( Functional groups) combine to form one single molecule together with In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are In Organic chemistry, an acyl chloride (or acid chloride) is an Organic compound which is a reactive derivative of a Carboxylic acid. g. with zinc chloride and glacial acetic acid at 145 °C it yields resacetophenone (HO)₂C₆H₃~CO. Zinc chloride is the name of Chemical compound with the formula Zn[[chlorine Cl]]2 and its hydrates Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste CH₃(M. Nencki and N. Sieber, Jour. prak. Chem. , 1881, 23, p. 147). With the anhydrides of dibasic acids it yields fluoresceins. In Chemistry, an anhydride is a compound that can be considered as derived from another compound by subtracting the molecules of water. Fluorescein is a Fluorophore commonly used in Microscopy, in a type of Dye laser as the Gain medium, in Forensics and Serology When heated with calcium chloride—ammonia to 200 °C it yields meta-dioxydiphenylamine (A. Calcium chloride (CaCl2 is an ionic compound of Calcium and Chlorine. Ammonia is a compound with the formula N[[hydrogen H3]] It is normally encountered as a Gas with a characteristic pungent Odor 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. Sodium nitrite, with Chemical formula Na[[Nitrogen N]] O 2 is used as a Color fixative and Preservative in meats and 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. An aldehyde is an organic compound containing a terminal Carbonyl group. Formaldehyde is a Chemical compound with the formula H2CO It is the simplest Aldehyde —an organic compound containing a terminal Carbonyl Hydrochloric acid is the Solution of Hydrogen chloride ( H[[Chlorine Cl]] in water Chloral hydrate is a Sedative and Hypnotic drug as well as a Chemical reagent and precursor lactone is a cyclic Ester in Organic chemistry. It is the condensation product of an Alcohol group and a Carboxylic acid 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. Nitric acid ( H[[nitrate NO3]] also known as Aqua fortis and spirit of nitre, is a highly corrosive and Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. Styphnic acid, or 246-trinitro-13-benzenediol is a yellow Astringent Acid that forms hexagonal Crystals It is used in the manufacture of Dyes

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. Antiseptics (from Greek αντί - anti, '"against" + σηπτικός - septikos, "putrefactive" are antimicrobial Disinfectants are Antimicrobial agents that are applied to non-living objects to destroy Microorganisms, the process of which is known as disinfection. Psoriasis (səˈraɪəsɪs ( suh-RI-uh-sus) is a non-contagious disorder which affects the Skin and Joints It commonly causes red scaly Eczema (from Greek έκζεμα) is a form of Dermatitis, or Inflammation of the Epidermis. It is present in over-the-counter topical acne treatments at 2% concentration, and in prescription treatments at higher concentrations. Acne vulgaris (commonly called acne) is a Skin disease caused by changes in the Pilosebaceous units (skin structures consisting of a Hair follicle Weak, watery solutions of resorcinol (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. Hay Fever is a comic play written by Noel Coward in 1924 and first produced in 1925 with Marie Tempest as the first Judith Bliss Pertussis, also known as whooping cough, is a highly contagious Disease caused by the Bacterium Bordetella pertussis; it derived its 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. Dandruff (also called scurf and historically termed Pityriasis capitis) is due to the excessive shedding of dead skin cells from the Scalp. Shampoo is a Hair care product used for the removal of oils, dirt skin particles Dandruff, environmental pollutants and other contaminant particles that Sunscreen (also known as sunblock or suntan lotion) is a Lotion, spray or other Topical product that absorbs or reflects the Sun 's It has also been employed in the treatment of gastric ulcers in doses of 125 to 250 mg in pills, and is said to be analgesic and haemostatic in its action. A peptic ulcer, also known as PUD or peptic ulcer disease, is an Ulcer (defined as mucosal erosions equal to or greater than 0 An antihemorrhagic ( antihaemorrhagic) agent is a substance that promotes Hemostasis (stops Bleeding) In large doses it is a poison causing giddiness, deafness, salivation, sweating and convulsions. In the context of Biology, poisons are substances that can cause damage, Illness, or Death to Organisms usually by Many different terms are often used to describe what is collectively known as dizziness. For the band see Saliva (band; for the village in Azerbaijan see Səliva. An epileptic seizure is caused by excessive and/or hypersynchronous electrical Neuronal activity and is usually self-limiting 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. Ultraviolet ( UV) light is Electromagnetic radiation with a Wavelength shorter than that of Visible light, but longer than X-rays

An emerging use of resorcinol is as a template molecule in supramolecular chemistry. Supramolecular chemistry refers to the area of Chemistry that focuses on the Noncovalent bonding interactions of molecules The -OH groups on resorcinol form hydrogen bonds to target molecules holding them in the proper orientation for a reaction. A hydrogen bond results from a Dipole-dipole force between an Electronegative atom and a Hydrogen atom bonded to Nitrogen, Oxygen 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. In the Physical sciences a phase is a Set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (see Green chemistry)

Resorcinol is an analytical reagent for the qualitative determinaion of ketoses (Seliwanoff's test). Green chemistry, also called sustainable chemistry is a chemical philosophy encouraging the design of products and processes that reduce or eliminate the use and generation of hazardous Seliwanoff’s test is utilized to differentiate between Aldose and Ketose Sugars The reagents consist of Resorcinol and conc

Resorcinol is the starting material for resorcinarene molecules. A resorcinarene (also resorcarene or calixresorcinarene) is a Macrocycle, or a cyclic Oligomer, based on the condensation of

Related compounds

Resazurin, C₁₂H₇NO₄, obtained by the action of nitrous acid on resorcinol ^[3], forms small dark red crystals possessing a greenish metallic glance. When dissolved in concentrated sulfuric 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-disulfonic 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 sulfuric acid on resorcin ^[4]. It is easily soluble in water and decomposes when heated to 100 °C.

References

External links

• International Chemical Safety Card 1033
• NIOSH Pocket Guide to Chemical Hazards
• IARC Monograph: "Resorcinol"
• European Chemicals Bureau
• IUPAC Nomenclature of Organic Chemistry (online version of the "Blue Book")

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