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Encyclopedia > Phenols

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. The simplest of the class is phenol (C6H5OH). Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... Look up chemical compound in Wiktionary, the free dictionary. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... This article is about the chemistry of hydrogen. ... An aromatic hydrocarbon (abbreviated as AH) or arene [1] is a hydrocarbon, the molecular structure of which incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ...

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). They have relatively higher acidities due to the aromatic ring tightly coupling with the oxygen and a relatively loose bond between the oxygen and hydrogen. 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). Loss of a positive hydrogen ion (H+) from the hydroxyl group of a phenol forms a negative phenolate ion. Chemical structure of Phenol selfmade by cacycle H Padleckas modified the previous image to make this new image on April 14-15, 2005 in order to include an alternate version of showing the phenol structure. ... Chemical structure of Phenol selfmade by cacycle H Padleckas modified the previous image to make this new image on April 14-15, 2005 in order to include an alternate version of showing the phenol structure. ... This article does not cite any references or sources. ... For other uses, see Acid (disambiguation). ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... This article is about the chemistry of hydrogen. ... In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted...


Some phenols are germicidal and are used in formulating disinfectants. Others possess estrogenic or endocrine disrupting activity. Estriol. ... Endocrine disruptors are substances which interfere with the endocrine system by mimicking, blocking or otherwise disrupting the function of hormones. ...

Contents

Synthesis of phenols

Several laboratory methods for the synthesis of phenols:

The Fries rearrangement is a rearrangement reaction of a phenyl ester to a hydroxy aryl ketone by catalysis of lewis acids . // Mechanism Despite many efforts a definitive reaction mechanism for the Fries rearrangement is not available. ... 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 or process in which a chemical compound is broken down by reaction with water. ... For other uses, see Ester (disambiguation). ... This article is about a general class of chemical compounds. ... A quinone (or benzoquinone) is either one of the two isomers of cyclohexadienedione or a derivative thereof. ... The Bucherer reaction in organic chemistry is the reversible conversion of Naphthol to naphtylamine in presence of ammonia and sodium bisulfite [1] [2] [3] [4] [5]. The French chemist Lepetit was the first to discover the reaction in 1898 but it was the German chemist Hans Bucherer who discovered (independent... Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ... In chemistry, azo compounds generally have a molecular formula of the form R-N=N-R, in which R and R can be either aromatic or aliphatic. ... This article needs to be wikified. ... 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 molecule. ... Image File history File links Size of this preview: 800 × 270 pixelsFull resolution‎ (1,006 × 339 pixels, file size: 6 KB, MIME type: image/png) Dienone phenol rearrangement I, the copyright holder of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms...

Reactions of phenols

Phenols react in a wide variety of ways.

Esterification is the general name for a chemical reaction in that an ester is the reaction product. ... This article is about a general class of chemical compounds. ... Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic system is replaced by an electrophile. ... In organic chemistry, a functional group is called an activating group if a benzene molecule to which it is attached more readily participates in electrophilic substitution reactions. ... A calixarene is a macrocycle or cyclic oligomer based on a hydroxyalkylation product of a phenol and an aldehyde [1]. The word calixarene is derived from calix or chalice because this type of molecule resembles a vase and from the word arene that refers to the aromatic building block. ... The Bucherer carbazole synthesis is a chemical reaction used to synthesize carbazoles from naphthols and aryl hydrazines using sodium bisulfite. ... A quinone (or benzoquinone) is either one of the two isomers of cyclohexadienedione or a derivative thereof. ... Fremys salt discovered in 1845 by Edmond Fremy (1814 - 1894) is a chemical compound and a strong oxidizing agent. ... Peroxymonosulfuric acid, also known as persulfuric acid and as Caros acid, is H2SO5, a colorless solid melting at 45 °C. In this acid, the S(VI) center adopts its characteristic tetrahedral geometry; the connectivity is indicated by the formula HO-O-S(O)2-OH. H2SO5 is sometimes confused... Molecular orbital diagram for singlet oxygen. ... Peroxymonosulfuric acid, also known as persulfuric acid and as Caros acid, is H2SO5, a colorless solid melting at 45 °C. In this acid, the S(VI) center adopts its characteristic tetrahedral geometry; the connectivity is indicated by the formula HO-O-S(O)2-OH. H2SO5 is sometimes confused... Sodium carbonate (also known as washing soda or soda ash), Na2CO3, is a sodium salt of carbonic acid. ... Acetonitrile is an organic molecule, often used as a solvent, with the chemical formula of CH3CN. Also known as methyl cyanide, it is the simplest of the organic nitriles. ... Organic peroxides are organic molecules containing the peroxide functional group ROOR If the R is hydrogen, the compound is called organic hydroperoxide. ... R-phrases R35 S-phrases Flash point Non flammable Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sodium thiosulfate (Na2S2O3) (sometimes spelled thiosulphate) is a colorless crystalline compound that is more familiar as the pentahydrate, Na2S2O3... Image File history File links Download high-resolution version (1047x199, 6 KB) Summary Oxone Phenol Dearomatization Licensing I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ... Benzenediols or dihydroxybenzenes are aromatic chemical compounds in which two hydroxyl groups are substituted onto a benzene ring. ... The Elbs persulfate oxidation is the chemical reaction of phenols with alkaline potassium persulfate to form para-diphenols. ... ... In chemistry, a ligand is an atom, ion or functional group that is bonded to one or more central atoms or ions, usually metals generally through co-ordinate covalent bond. ... An ion is an atom or group of atoms with a net electric charge. ...

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.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 -

Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... Flash point 127 °C R/S statement R: 22-36 37 38 S: 26-36 RTECS number GO7875000 Related compounds Related compounds butylated hydroxyanisole Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references BHT is the common... Space-filling model of the antioxidant metabolite glutathione. ... Food additives are substances added to food to preserve flavor or improve its taste and appearance. ... Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is the active component of chilli peppers, which are plants belonging to the genus Capsicum. ... The chile pepper (also chili or chilli; from Spanish chile) is the fruit of the plant Capsicum from the nightshade family (Solanaceae). ... This article needs to be wikified. ... Binomial name Piper betle L. The Betel (Piper betle) is a spice whose leaves have medicinal properties. ... Cresols are organic chemical compounds which are methylphenols. ... Coal tar is the liquid by-product of the distillation of coal to make coke. ... Creosote is the name used for a variety of products: wood creosote, coal tar creosote, coal tar, coal tar pitch, and coal tar pitch volatiles. ... Estradiol (17β-estradiol) (also oestradiol) is a sex hormone. ... Estriol. ... Eugenol (C10H12O2), is an allyl chain-substituted guaiacol, i. ... An essential oil is a concentrated, hydrophobic liquid containing volatile aromatic compounds from plants. ... Binomial name (L.) Merrill & Perry A single dried clove flower bud Cloves (Syzygium aromaticum, syn. ... Chemical structure of gallic acid Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. ... Chemical structure of guaiacol Guaiacol, or 2-methoxyphenol, is a natural organic compound with the molecular formula C7H8O2. ... This article is about flavor as a sensory impression. ... Wikibooks Cookbook has more about this subject: Roasting Roasting is a cooking method that utilizes dry heat, whether an open flame, oven, or other heat source. ... For other uses, see Coffee (disambiguation). ... For other uses, see Whisky (disambiguation). ... This article does not cite any references or sources. ... Nonylphenol is an organic compound of the wider family of alkylphenols. ... A detergent is a compound, or a mixture of compounds, 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, but is also widely used in contraceptives for its spermicidal properties. ... Orthophenyl phenol Orthophenyl phenol, 2-phenyl phenol, o-phenyl phenol, 2-hydroxybiphenyl, o-xenol, or orthoxenol, is a phenolic biocide used as a preservative. ... A Fungicide is one of three main methods of pest control- chemical control of fungi in this case. ... Species & major hybrids Species Citrus maxima - Pomelo Citrus medica - Citron Citrus reticulata - Mandarin & Tangerine Major hybrids Citrus x aurantifolia - Lime Citrus x aurantium - Bitter Orange Citrus x bergamia - Bergamot Citrus x hystrix - Kaffir Lime Citrus x ichangensis - Ichang Lemon Citrus x limon - Lemon Citrus x limonia - Rangpur Citrus x paradisi... Picric acid is the common term for the chemical compound 2,4,6-trinitrophenol, also known as TNP; the material is a yellow crystalline solid. ... This article is concerned solely with chemical explosives. ... Phenolphthalein is a sensitive chemical with the formula C20H14O4 (often written as HIn in shorthand notation). ... Acids and bases: Acid-base extraction Acid-base reaction Acid dissociation constant Acidity function Buffer solutions pH Proton affinity Self-ionization of water Acids: Lewis acids Mineral acids Organic acids Strong acids Superacids Weak acids Bases: Lewis bases Organic bases Strong bases Superbases Non-nucleophilic bases Weak bases edit A... Polyphenols are a group of chemical substances found in plants, characterized by the presence of more than one phenol group per molecule. ... Molecular structure of the flavone backbone (2-phenyl-1,4-benzopyrone) The term flavonoid refers to a class of plant secondary metabolites. ... A bottle of tannic acid. ... Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries. ... Cultivated raspberries The raspberry (plural, raspberries) is the edible fruit of a number of species of the genus Rubus. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... For other uses, see Dopamine (disambiguation). ... Epinephrine (INN) or adrenaline (BAN) is a hormone and a neurotransmitter. ... Norepinephrine, known as noradrenaline outside the USA, is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... Neurotransmitters are chemicals that are used to relay, amplify and modulate electrical signals between a presynaptic and a postsynaptic neuron. ... Thymol is a phenol derivative of cymene, C10H13OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. ... An antiseptic solution of Povidone-iodine applied to an abrasion Antiseptics (Greek αντί, against, and σηπτικός, putrefactive) are antimicrobial substances that are applied to living tissue/skin to reduce the possibility of infection, sepsis, or putrefaction. ... For the Kate Nash song see Mouthwash (song) For the ska-punk band, see Mouthwash (band) Mouthwash or mouth rinse is a product used for oral hygiene. ... Tyrosine (from the Greek tyros, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese[1][2]), 4-hydroxyphenylalanine, or 2-amino-3(4-hydroxyphenyl)-propanoic acid, is one of the 20 amino acids that are used by cells... This article is about the class of chemicals. ... Xylenol or dimethylphenol is a benzene derivative with two methyl groups and a hydroxyl group. ...

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 essental 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.

Cannabinoids are a group of terpenophenolic compounds present in Cannabis (Cannabis sativa L). ... Binomial name Linnaeus Subspecies L. subsp. ... Diethylstilbestrol (DES) is a drug, a synthetic nonsteroidal estrogen that was first synthesized in 1938. ... For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids. ... // Therapeutic use L-DOPA is used to replace dopamine lost in Parkinsons disease because dopamine itself cannot cross the blood-brain barrierwhere its precursor can. ... For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids. ... Methyl salicylate (chemical formula C6H4(HO)COOCH3; also known as salicylic acid methyl ester, oil of wintergreen, betula oil, methyl-2-hydroxybenzoate) is a natural product of many species of plants. ... Wintergreen is a term that can refer to various groups of plants: Wintergreen once commonly referred to plants that continue photosynthesis (remain green) throughout the winter. ... Propofol is a short-acting intravenous anesthetic agent used for the induction of general anesthesia in adult patients and pediatric patients older than 3 years of age; maintenance of general anesthesia in adult patients and pediatric patients older than 2 months of age; and sedation in medical contexts, such as... Anesthesia or anaesthesia (see spelling differences) has traditionally meant the condition of having the perception of pain and other sensations blocked. ... Psilocin,(4-HO-DMT) sometimes called psilocine or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. ... The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories: psychedelics, dissociatives, and deliriants. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Type species Psilocybe montana Species List of Psilocybe species Psilocybe is a genus of small mushrooms growing worldwide. ... For other uses, see Mushroom (disambiguation). ... 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 C6H4(OH)CO2H, where the OH group is adjacent to the carboxyl group. ... Plant hormones (also known as plant growth regulators (PGRs) and phytohormones) are chemicals that regulate a plants growth. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Antipyretics are drugs that prevent or reduce fever by lowering the body temperature from a raised state. ... Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. ... This article is about the drug. ... 200ml TCP bottle TCP is a mild antiseptic, produced and sold in the United Kingdom by Pfizer. ... 200ml TCP bottle TCP is a mild antiseptic, produced and sold in the United Kingdom by Pfizer. ...

References

  1. ^ related to quinones, see for example the Zincke-Suhl reaction
  2. ^ Advanced organic Chemistry, Reactions, mechanisms and structure 3ed. page Jerry March ISBN 0-471-85472-7
  3. ^ p-tert-butylcalix[8]arene, Organic Syntheses, CV 8, 80 Article
  4. ^ 2,4-Hexadienedioic acid, monomethyl ester, (Z,Z)- Organic Syntheses, Coll. Vol. 8, p.490 (1993); Vol. 66, p.180 (1988) Article
  5. ^ 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl Organic Syntheses, Coll. Vol. 6, p.1010 (1988); Vol. 52, p.83 (1972) Abstract.
  6. ^ 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

A quinone (or benzoquinone) is either one of the two isomers of cyclohexadienedione or a derivative thereof. ... The Zincke-Suhl reaction is a special case of a Friedel-Crafts alkylation and was first described by Zincke and Suhl [1] [2] [3]: The classic example of this reaction is the conversion of p-cresol to a cyclohexadienone with the aid of aluminum chloride as a catalyst and tetrachloromethane... Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ...

External links

  • Special Issue on Phenolics (flavonoids and non-flavonoids)

  Results from FactBites:
 
an introduction to phenol (593 words)
Phenol is the simplest member of a family of compounds in which an -OH group is attached directly to a benzene ring.
Phenol itself is the only one of the family that you are likely to need to know about for UK A level purposes.
Phenol is somewhat soluble in water because of its ability to form hydrogen bonds with the water.
Phenol (4471 words)
On exposure to air and light, phenol assumes a pinkish or reddish discoloration; this discoloration is accelerated by the presence of alkalinity or impurities.
Phenol may act as a nonspecific irritant to promote the development of tumors when it is repeatedly applied in large amounts to the skin [Hathaway et al.
Chronic phenol poisoning is characterized by systemic disorders such as digestive disturbances, nervous system effects, and possibly by skin discoloration and eruptions; the prognosis is grave when there is extensive damage to the liver and kidneys [Parmeggiani 1983].
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