In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-O H) attached to an aromatic hydrocarbon group. Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 The simplest of the class is phenol (C6H5OH). Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell"
Phenol - the simplest of the phenols.
Although similar to alcohols, phenols have unique properties and are not classified as alcohols (since the hydroxyl group is not bonded to a saturated carbon atom). In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon They have relatively higher acidities due to the aromatic ring's tight coupling with the oxygen and a relatively loose bond between the oxygen and hydrogen. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually comprised between 10 and 12). In Organic chemistry, compounds composed of Carbon and Hydrogen are divided into two classes Aromatic compounds which contain Benzene rings Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Loss of a positive hydrogen ion (H+) from the hydroxyl group of a phenol forms a negative phenolate ion.
Some phenols are germicidal and are used in formulating disinfectants. Others possess estrogenic or endocrine disrupting activity. Estrogens (US otherwise oestrogens or œstrogens) are a group of Steroid compounds named for their importance in the Estrous cycle, Endocrine disruptors (sometimes also referred to as hormonally active agents) are Exogenous substances that act like Hormones in the Endocrine system
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Synthesis of phenols
Several laboratory methods for the synthesis of phenols:
- by an ester rearrangement in the Fries rearrangement
- by a rearrangement of N-phenylhydroxylamines in the Bamberger rearrangement
- by hydrolysis of phenolic esters or ethers
- by reduction of quinones
- by replacement of an aromatic amine by an hydroxyl group with water and sodium bisulfide in the Bucherer reaction
- by hydrolysis of diazonium salts
- by oligomerisation with formaldehyde + base catalysed reaction with epichlorohydrine to epoxi resin components
- by reaction with acetone/ketones to e. The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a Rearrangement reaction of a Phenyl Ester to a Hydroxy The Bamberger rearrangement is the Chemical reaction of N-phenylhydroxylamines with strong Aqueous Acid, which will rearrange to give 4-aminophenols Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl "DDQ" redirects here DDQ is also the former callsign of a TV station in Toowoomba Queensland Australia The Bucherer reaction in Organic chemistry is the reversible conversion of Naphthol to naphtylamine in presence of Ammonia and Sodium bisulfite Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions Diazonium compounds or diazonium salts are a group of Organic compounds sharing a common Functional group with the characteristic structure of R-N2+ g. Bisphenol A, an important monomer for resins, e. Bisphenol A, commonly abbreviated as BPA, is an Organic compound with two Phenol Functional groups It is a difunctional building block of g. polycarbonate(PC), epoxi resins
- by a rearrangement reaction of dienones [1] in the dienone phenol rearrangement [2]:
Reactions of phenols
Phenols react in a wide variety of ways. A rearrangement reaction is a broad class of Organic reactions where the carbon skeleton of a Molecule is rearranged to give a Structural isomer of the original
- Esterfication reactions and ether formation
- Electrophilic aromatic substitutions as the hydroxyl group is activating, for example synthesis of calixarenes [3]
- Reaction of naphtols and hydrazines and sodium bisulfite in the Bucherer carbazole synthesis
- Oxidative cleavage, for instance cleavage of 1,2-dihydroxybenzene to the monomethylester of 2,4 hexadienedioic acid with oxygen, copper chloride in pyridine [4]
- Oxidative de-aromatization to quinones also known as the Teuber reaction. Esterification is the general name for a Chemical reaction in which two reactants (typically an alcohol and an acid form an Ester as the reaction product Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl Electrophilic aromatic substitution or EAS is an Organic reaction in which an atom usually Hydrogen, appended to an aromatic system is replaced In Organic chemistry, a Functional group is called an activating group if a Benzene Molecule to which it is attached more readily participates A calixarene is a Macrocycle or cyclic Oligomer based on a Hydroxyalkylation product of a Phenol and an Aldehyde. The Bucherer carbazole synthesis is a Chemical reaction used to synthesize Carbazoles from Naphthols and aryl Hydrazines using Sodium bisulfite "DDQ" redirects here DDQ is also the former callsign of a TV station in Toowoomba Queensland Australia Oxidizing reagents are Fremy's salt [5] and oxone [6]. Potassium peroxymonosulfate, K[[hydrogen H]] S[[oxygen O]]5 is widely used as an Oxidizing agent. In reaction depicted below 3,4,5-trimethylphenol reacts with singlet oxygen generated from oxone/sodium carbonate in an acetonitrile/water mixture to a para-peroxyquinole. Singlet oxygen is the common name used for the two Metastable states of molecular Oxygen (O2 with higher energy than the ground state Triplet oxygen Potassium peroxymonosulfate, K[[hydrogen H]] S[[oxygen O]]5 is widely used as an Oxidizing agent. Sodium carbonate (also known as washing soda or soda ash), is a Sodium Salt of Carbonic acid. Acetonitrile (ACN is the Chemical compound with formula CH3CN This hydroperoxide is oxidized to the quinole with sodium thiosulfate. Organic peroxides are Organic compounds containing the Peroxide Functional group (ROOR' Sodium thiosulfate ( Na 2 S 2 O 3 is a colorless Crystalline compound that is more familiar as the Pentahydrate
- Phenols are oxidized to benzenediols in the Elbs persulfate oxidation
- Phenolate anions (deriving from phenols by the loss of H+) can act as ligands towards metal cations
Phenolic compounds
- For a full list, see Category:Phenols
| Phenol | the parent compound, used as an disinfectant and for chemical synthesis |
| BHT | (butylated hydroxytoluene) - a fat-soluble antioxidant and food additive |
| Capsaicin | the pungent compound of chilli peppers |
| Bisphenol A | and other bisphenols produced from ketones and phenol / cresol |
| Chavibetol | from betel, used as a flavouring |
| Cresol | found in coal tar and creosote |
| Estradiol | estrogen - hormones |
| Eugenol | the main constituent of the essential oil of clove |
| Gallic acid | found in gallnuts |
| Guaiacol | (2-methoxyphenol) - has a smokey flavor, and is found in roasted coffee, whisky, and smoke |
| 4-Nonylphenol | a breakdown product of detergents and nonoxynol-9 |
| Orthophenyl phenol | a fungicide used for waxing citrus fruits |
| Picric acid | (trinitrophenol) - an explosive material |
| Phenolphthalein | pH indicator |
| Polyphenol | e. Benzenediols or dihydroxybenzenes are Aromatic Chemical compounds and Polyphenols in which two Hydroxyl groups are substituted onto a The Elbs persulfate oxidation is the Organic reaction of Phenols with alkaline Potassium persulfate to form para -diphenols An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge In Chemistry, a ligand is either an Atom, Ion, or Molecule (see also Functional group) that bonds to a central metal generally An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" In Chemistry, chemical synthesis is purposeful execution of Chemical reactions in order to get a product, or several products An antioxidant is a Molecule capable of slowing or preventing the oxidation of other molecules Food additives are substances added to food to preserve flavour or improve its taste and appearance Capsaicin /ˌkæpˈseˌɪsɪn/ (8- Methyl - N - Vanillyl -6-nonen Amide) is the active component of Chili peppers The chili pepper, chilli pepper, or chili, is the fruit of the plants from the Genus Capsicum, which are members of the nightshade Bisphenol A, commonly abbreviated as BPA, is an Organic compound with two Phenol Functional groups It is a difunctional building block of The Betel ( Piper betle) is the leaf of a vine belonging to the Piperaceae family which includes pepper and Kava) Cresols are Organic compounds which are methyl[[phenol]]s They are a widely occurring natural and manufactured group of Aromatic Organic compounds Coal tar is a brown or black liquid of high Viscosity, which smells of Naphthalene and Aromatic hydrocarbons Coal tar is among the by-products when coal Creosote is the name used for a variety of products including wood creosote and coal tar creosote. Estradiol (17β-estradiol (also oestradiol) is a Sex hormone. Estrogens (US otherwise oestrogens or œstrogens) are a group of Steroid compounds named for their importance in the Estrous cycle, Eugenol (C10H12O2 is an allyl chain-substituted Guaiacol. Eugenol is a member of the Phenylpropanoids class of chemical compounds An essential oil is a concentrated Hydrophobic Liquid containing volatile Aroma compounds from Plants They are also known as volatile This article is about the Spice; for other meanings see Clove (disambiguation. Gallic acid is an Organic acid, also known as 345-trihydroxy Benzoic acid, found in Gallnuts Sumac, Witch hazel, Tea leaves Guaiacol is a naturally occurring Organic compound with the formula C6H4(OH(OCH3 Flavor or flavour is the sensory impression of a Food or other substance, and is determined CoFFEE is an Open source Software for computer supported collaborative learning (CSCL in a digital classroom Whisky (uisge-beatha or whiskey (uisce beatha or fuisce) refers to a broad category of Alcoholic beverages that are distilled from fermented Smoke is the collection of airborne solid and liquid Particulates and Gases ref> ''Smoke Production and Properties'' - SFPE Handbook of Fire Protection Engineering Nonylphenol is an organic compound of the wider family of Alkylphenols It is a product of industrial synthesis formed during the Alkylation process of Phenols A detergent (as a noun is a material intended to assist Cleaning. Nonoxynol-9, sometimes abbreviated as N-9, is a non-ionic Nonoxynol Surfactant that is used as an ingredient in various cleaning and cosmetic products 2-Phenylphenol, or o -phenylphenol is an Organic compound that consists of two linked Benzene rings and a Phenolic hydroxyl group Fungicides are Chemical compounds or biological organisms used to kill or inhibit fungi or fungal spores Citrus is a common term and Genus of Flowering plants in the family Rutaceae, originating in tropical and subtropical southeast regions of "TNP" redirects here For the airport with the IATA airport code TNP see Twentynine Palms Airport. An explosive material is a material that either is chemically or otherwise Energetically unstable or produces a sudden expansion of the material usually accompanied Phenolphthalein is a Chemical compound with the formula C 20 H 14 O 4 (often written as " HIn A pH indicator is a halochromic chemical compound that is added in small amounts to a Solution so that the PH ( Acidity or Polyphenols are a group of chemical substances found in plants characterized by the presence of more than one Phenol unit or building block per molecule g. flavonoids and tannins |
| Raspberry ketone | a compound with an intense raspberry smell |
| Serotonin / dopamine / adrenaline / noradrenaline | natural neurotransmitters |
| Thymol | (2-Isopropyl-5-methyl phenol) - an antiseptic that is used in mouthwashes |
| Tyrosine | an amino acid |
| Xylenol | -used in antiseptics & disinfecticides |
Medicinals
| Cannabinoids | the active constituents of cannabis |
| Diethylstilbestrol | a synthetic estrogen with a stilbene structure |
| L-DOPA | a synthetic estrogen with a stilbene structure |
| Methyl salicylate | the major constituent of the essential oil of wintergreen |
| Propofol | a short-acting intravenous anesthetic agent |
| Psilocin | a hallucinogenic alkaloid of Psilocybe mushrooms |
| Salicylic acid | a plant hormone used for its analgesic, antipyretic, and anti-inflammatory properties, also a precursor compound to Aspirin |
| Trichlorophenylmethyliodosalicyl | the main component of TCP, an antiseptic. The term flavonoid (or bioflavonoid refers to a class of Plant Secondary metabolites According to the IUPAC nomenclature they can be classified into Tannins are Astringent, bitter plant Polyphenols that either bind and Precipitate or shrink Proteins The astringency from the tannins is what Raspberry ketone is a natural phenolic compound that is the primary Aroma compound of red raspberries. The raspberry (plural raspberries) is the edible Fruit of a multitude of plant species in the subgenus Idaeobatus of the genus Rubus Serotonin (ˌsɛrəˈtoʊnən ( 5-hydroxytryptamine, or 5-HT) is a Monoamine Neurotransmitter synthesized in serotonergic Neurons Dopamine is a Hormone and Neurotransmitter occurring in a wide variety of animals including both vertebrates and invertebrates Norepinephrine ( INN) (abbreviated norepi or NE) or noradrenaline ( BAN) (abbreviated NA or NAd) is a See Chemical synapse for an introduction to concepts and terminology used in this article Thymol is a Monoterpene phenol derivative of Cymene, C10H14OH Isomeric with Carvacrol, found in oil of Antiseptics (from Greek αντί - anti, '"against" + σηπτικός - septikos, "putrefactive" are antimicrobial Mouthwash or mouth rinse is a product used for Oral hygiene. Antiseptic and anti-plaque mouth rinse claims to kill the bacterial plaque Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 20 Amino acids that are used by cells to synthesize In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Xylenol or dimethylphenol is an Arene compound with two Methyl groups and a Hydroxyl group Cannabinoids ( are a group of terpeno[[phenol]]ic compounds present in Cannabis ( Cannabis sativa L Cannabis sativa is an annual plant in the Cannabaceae family It is a Herb that has been used throughout recorded history by humans for various purposes Diethylstilbestrol ( DES) is a drug, an orally active synthetic nonsteroidal Estrogen that was first synthesized in 1938 Stilbene may refer to (E-Stilbene (Z-Stilbene Stilbene may refer to (E-Stilbene (Z-Stilbene Methyl salicylate ( Chemical formula C6H4(HOCOOCH3 also known as salicylic acid methyl ester, oil of wintergreen, Wintergreen is a group of plants Wintergreen once commonly referred to Plants that continue Photosynthesis (remain Green) throughout the Winter Propofol is a short-acting Intravenous sedative agent used for the induction of general Anesthesia for adults and children maintenance of general anesthesia and Anesthesia, or anaesthesia (see spelling differences; from Greek grc αν- an-, "without" and grc αἲσθησις Psilocin (4-HO-DMT sometimes also (misspelled psilocine, psilocyn, or psilotsin, is a psychedelic ( hallucinogenic) Mushroom The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories Psychedelics, Dissociatives This article is about the chemical compounds alkaloids For the Pharmaceutical company in the Republic of Macedonia see Alkaloid (company. Psilocybe is a Genus of small Mushrooms growing worldwide This genus is best known for its species with hallucinogenic properties widely A mushroom is the fleshy Spore -bearing Fruiting body of a Fungus, typically produced above ground on soil or on its food source Salicylic acid (from the Latin word for the willow tree Salix, from whose bark it can be obtained is a Beta hydroxy acid (BHA with the formula Plant hormones (also known as phytohormones) are chemicals that regulate plant growth Antipyretics are Drugs that reduce body temperature in situations such as Fever. Anti-inflammatory refers to the property of a substance or treatment that reduces Inflammation. Aspirin, or acetylsalicylic acid (ASA (əˌsɛtɨlsælɨˌsɪlɨk ˈæsɨd is a Salicylate drug, often used as an Analgesic to relieve TCP is a mild Antiseptic, produced and sold in the United Kingdom by Pfizer. TCP is a mild Antiseptic, produced and sold in the United Kingdom by Pfizer. |
References
- ^ related to quinones, see for example the Zincke-Suhl reaction
- ^ Advanced organic Chemistry, Reactions, mechanisms and structure 3ed. "DDQ" redirects here DDQ is also the former callsign of a TV station in Toowoomba Queensland Australia The Zincke-Suhl reaction is a special case of a Friedel-Crafts alkylation and was first described by Theodor Zincke and Suhl page Jerry March ISBN 0-471-85472-7
- ^ p-tert-butylcalix[8]arene, Organic Syntheses, CV 8, 80 Article
- ^ 2,4-Hexadienedioic acid, monomethyl ester, (Z,Z)- Organic Syntheses, Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 8, p. 490 (1993); Vol. 66, p. 180 (1988) Article
- ^ 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl Organic Syntheses, Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 6, p. 1010 (1988); Vol. 52, p. 83 (1972) Abstract.
- ^ Oxidative De-aromatization of para-Alkyl Phenols into para-Peroxyquinols and para-Quinols Mediated by Oxone as a Source of Singlet Oxygen M. Carmen Carreño, Marcos González-López, Antonio Urbano Angewandte Chemie International Edition Volume 45, Issue 17 , Pages 2737 - 2741 2006 Abstract
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