[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/o-cresol-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki41\/o-cresol-wikipedia\/","headline":"o-Cresol – Wikipedia","name":"o-Cresol – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia o-Cresol Names Preferred IUPAC name Systematic IUPAC name after-content-x4 Other names after-content-x4 2-Cresolo-Cresolortho-Cresolortho-Toluenolortho-Benzol2-Hydroxytolueneo-Cresylic acid1-Hydroxy-2-methylbenzene","datePublished":"2019-11-06","dateModified":"2019-11-06","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki41\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/0\/0b\/O-Kresol.svg\/110px-O-Kresol.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/0\/0b\/O-Kresol.svg\/110px-O-Kresol.svg.png","height":"102","width":"110"},"url":"https:\/\/wiki.edu.vn\/en\/wiki41\/o-cresol-wikipedia\/","wordCount":3867,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopediao-CresolNamesPreferred IUPAC nameSystematic IUPAC name       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Other names       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x42-Cresolo-Cresolortho-Cresolortho-Toluenolortho-Benzol2-Hydroxytolueneo-Cresylic acid1-Hydroxy-2-methylbenzeneIdentifiers3DMet506917ChEBIChEMBLChemSpiderECHA InfoCard100.002.204 EC Number101619KEGGMeSH2-CresolRTECS numberUNIIUN number2076, 3455InChI=1S\/C7H8O\/c1-6-4-2-3-5-7(6)8\/h2-5,8H,1H3\u00a0YKey:\u00a0QWVGKYWNOKOFNN-UHFFFAOYSA-N\u00a0NPropertiesC7H8OMolar mass108.140\u00a0g\u00b7mol\u22121AppearanceColorless to white crystalsOdorsweet, phenolic odorDensity1.0465 g\u00a0cm\u22123Melting point31\u00a0\u00b0C; 88\u00a0\u00b0F; 304\u00a0KBoiling point191\u00a0\u00b0C; 376\u00a0\u00b0F; 464\u00a0K31 g\u00a0dm\u22123 (at 40\u00a0\u00b0C)Solubilitysoluble in chloroform, ether, CCl4Solubility in ethanolMiscible (at 30\u00a0\u00b0C)Solubility in diethyl etherMiscible (at 30\u00a0\u00b0C)log P1.962Vapor pressure40 Pa (at 20\u00a0\u00b0C)Acidity (pKa)10.316Basicity (pKb)3.681\u221272.9\u00d710\u22126\u00a0cm3\/mol1.5353Viscosity35.06 cP (at 45\u00a0\u00b0C)Thermochemistry154.56 J\u00a0K\u22121\u00a0mol\u22121165.44 J\u00a0K\u22121\u00a0mol\u22121\u2212204.3 kJ\u00a0mol\u22121\u22123.6936 MJ\u00a0mol\u22121HazardsGHS labelling:DangerH301, H311, H314P260, P264, P270, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P405, P501NFPA 704 (fire\u00a0diamond)Flash point81\u00a0\u00b0C (178\u00a0\u00b0F; 354\u00a0K)598.9\u00a0\u00b0C (1,110.0\u00a0\u00b0F; 872.0\u00a0K)Explosive limits1.4%\u2013? (148\u00a0\u00b0C)[1]Lethal dose or concentration (LD, LC):1350 mg\/kg (rat, oral)121 mg\/kg (rat, oral)344 mg\/kg (mouse, oral)[2]NIOSH (US health exposure limits):TWA 5 ppm (22 mg\/m3) [skin][1]TWA 2.3 ppm (10 mg\/m3)[1]250 ppm[1]Safety data sheet (SDS)External MSDSRelated compoundsCresols:Except where otherwise noted, data are given for materials in their standard state (at 25\u00a0\u00b0C [77\u00a0\u00b0F], 100\u00a0kPa).Chemical compoundortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.[3]       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Table of ContentsNatural occurrences[edit]Production[edit]Applications[edit]Health effects[edit]References[edit]External links[edit]Natural occurrences[edit]o-Cresol is one of the chemical compounds found in castoreum. This compound is gathered from the beaver’s castor glands and found in the white cedar consumed by the beaver.[4]o-Cresol is a constituent of tobacco smoke.[5]Production[edit]Together with many other compounds, o-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from coal. A similar source material is petroleum residues.  These residue contains a few percent by weight of phenol and isomeric cresols. In addition to the materials derived from these natural sources, about two thirds of the Western world’s supply is produced by methylation of phenol using methanol. The alkylation is catalysed by metal oxides:C6H5OH + CH3OH \u2192 CH3C6H4OH + H2OOver-methylation gives xylenol. Many other production methods have been examined, including oxidative decarboxylation of salicylic acid, oxygenation of toluene, and hydrolysis of 2-chlorotoluene.[3]Applications[edit]o-Cresol is mainly used as a precursor to other compounds. Chlorination and etherification gives members of commercially important herbicides, such as 2-methyl-4-chlorophenoxyacetic acid (MCPA). Nitration gives dinitrocresol, a popular herbicide. Kolbe\u2013Schmitt carboxylation gives o-cresotinic acid, a pharmaceutical intermediate. Carvacrol, essence of oregano, is derived by alkylation of o-cresol with propene. The muscle relaxant mephenesin is an ether derived from o-cresol.[3]Health effects[edit]Most exposures to cresols are at very low levels that are not harmful although, like phenols, cresols are skin irritants. When cresols are inhaled, ingested, or applied to the skin at very high levels, they can be harmful. Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols at lower levels over longer times. The acute LD50 for oral ingestion by mice is 344\u00a0mg\/kg.[3]References[edit]^ a b c d NIOSH Pocket Guide to Chemical Hazards. “#0154”. National Institute for Occupational Safety and Health (NIOSH).^ “Cresol (o, m, p isomers)”. Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).^ a b c d Helmut Fiegein “Cresols and Xylenols” in Ullmann’s Encyclopedia of Industrial Chemistry” 2007; Wiley-VCH, Weinheim. doi:10.1002\/14356007.a08_025^ The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)^ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). “Hazardous Compounds in Tobacco Smoke”. International Journal of Environmental Research and Public Health. 8 (12): 613\u2013628. doi:10.3390\/ijerph8020613. ISSN\u00a01660-4601. PMC\u00a03084482. PMID\u00a021556207.External links[edit]     (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4"},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki41\/o-cresol-wikipedia\/#breadcrumbitem","name":"o-Cresol – Wikipedia"}}]}]