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{{DISPLAYTITLE:''o''-Cresol}} |
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{{DISPLAYTITLE:''o''-Cresol}} |
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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 415868101 |
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| Watchedfields = changed |
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| Name = ''o''-Cresol |
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| verifiedrevid = 416907599 |
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| ImageFile = O-Kresol.svg |
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| Name = ''o''-Cresol |
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| ImageSize = 120px |
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| ImageName = o-cresol |
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| ImageFileL1 = O-Kresol.svg |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Ortho-cresol-3D-vdW.png |
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| ImageNameL1 = Kekulé, skeletal formula of ''o''-cresol with some implicit hydrogens shown |
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| ImageSize1 = 150px |
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| ImageFileR1 = Ortho-cresol-3D-vdW.png |
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| ImageName1 = 3D model of o-cresol |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = 2-Hydroxytoluene<br/>''ortho''-cresol |
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| ImageNameR1 = Spacefill model of ''o''-cresol |
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| IUPACName = 2-Methylphenol |
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| PIN = 2-Methylphenol |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = 2-Methylbenzenol |
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| CASNo = 95-48-7 |
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| OtherNames = 2-Cresol<br />''o''-Cresol<br />''ortho''-Cresol<br />''ortho''-Toluenol<br />''ortho''-Benzol<br />2-Hydroxytoluene<br />''o''-Cresylic acid<br />1-Hydroxy-2-methylbenzene |
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| CASNo_Ref = {{cascite}} |
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|Section1={{Chembox Identifiers |
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| RTECS = GO6300000 |
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| SMILES = Cc1ccccc1O |
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| CASNo = 95-48-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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}} |
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| PubChem = 335 |
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| Section2 = {{Chembox Properties |
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| EINECS = 202-423-8 |
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| Appearance = colorless crystals or liquid |
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| UNNumber = 2076, 3455 |
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| Formula = C<sub>7</sub>H<sub>8</sub>O |
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| KEGG = C01542 |
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| MolarMass = 108.14 g/mol |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| Density = 1.0465 g/cm³, liquid at 20 °C |
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| MeSHName = 2-Cresol |
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| Solubility = 3.1 g/100 ml at 40 °C<br>5.6 g/100 ml at 100 °C |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| Solubility1 = fully ] at > 30 °C |
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| Solvent1 = ethanol |
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| ChEBI = 28054 |
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| ChEMBL = 46931 |
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| Solubility2 = fully ] at > 30 °C |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Solvent2 = diethyl ether |
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| RTECS = GO6300000 |
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| MeltingPt = 29.8 °C |
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| Beilstein = 506917 |
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| BoilingPt = 191.5 °C |
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| Gmelin = 101619 |
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| RefractIndex = 1.5353 |
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| 3DMet = B00313 |
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| Viscosity = 35.06 c] at 45 °C |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| pKa = 10.26 |
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| UNII = YW84DH5I7U |
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}} |
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| SMILES = Cc1ccccc1O |
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| Section7 = {{Chembox Hazards |
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| StdInChI = 1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3 |
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| MainHazards = Highly toxic. May be fatal if inhaled, swallowed or absorbed through skin. Experimental neoplastigen. Human mutagenic data. Readily absorbed through the skin. Very destructive of mucous membranes. Causes burns. Inhalation may cause spasm. Severe skin and eye irritant. |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ExternalMSDS = |
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| StdInChIKey = QWVGKYWNOKOFNN-UHFFFAOYSA-N |
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| FlashPt = 81 °C |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| RPhrases = {{R24}} {{R25}} {{R34}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SPhrases = {{S37}} {{S39}} {{S45}} |
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| ChemSpiderID = 13835772 |
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| NFPA-H = 3 |
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}} |
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| NFPA-F = 2 |
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|Section2={{Chembox Properties |
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| NFPA-R = 0 |
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| Appearance = Colorless to white crystals |
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| NFPA-O = |
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| Odor = sweet, phenolic odor |
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}} |
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| C=7 | H=8 | O=1 |
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| Section8 = {{Chembox Related |
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| Density = 1.0465 g cm<sup>−3</sup> |
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| Function = ]s |
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| Solubility = 31 g dm<sup>−3</sup> (at 40 °C) |
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| OtherFunctn = ], ], ] |
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| Solvent1 = ethanol |
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}} |
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| Solubility1 = Miscible (at 30 °C) |
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| Solvent2 = diethyl ether |
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| Solubility2 = Miscible (at 30 °C) |
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| SolubleOther = soluble in ], ], ] |
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| MeltingPtK = 304 |
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| BoilingPtK = 464 |
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| RefractIndex = 1.5353 |
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| LogP = 1.962 |
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| VaporPressure = 40 Pa (at 20 °C) |
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| pKa = 10.316 |
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| pKb = 3.681 |
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| Viscosity = 35.06 cP (at 45 °C) |
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| MagSus = {{val|-72.9e-6|u=cm<sup>3</sup>/mol}} |
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}} |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −204.3 kJ mol<sup>−1</sup> |
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| DeltaHc = −3.6936 MJ mol<sup>−1</sup> |
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| Entropy = 165.44 J K<sup>−1</sup> mol<sup>−1</sup> |
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| HeatCapacity = 154.56 J K<sup>−1</sup> mol<sup>−1</sup> |
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}} |
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|Section4={{Chembox Hazards |
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| ExternalSDS = |
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| GHSPictograms = {{GHS05}}{{GHS06}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|311|314}} |
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| PPhrases = {{P-phrases|260|264|270|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|322|330|361|363|405|501}} |
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| NFPA-H = 3 |
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| NFPA-F = 2 |
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| NFPA-R = 0 |
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| FlashPtC = 81 |
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| AutoignitionPtC = 598.9 |
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| LD50 = 1350 mg/kg (rat, oral)<br />121 mg/kg (rat, oral)<br />344 mg/kg (mouse, oral)<ref>{{IDLH|cresol|Cresol (o, m, p isomers)}}</ref> |
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| PEL = TWA 5 ppm (22 mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0154}}</ref> |
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| ExploLimits = 1.4%–? (148 °C)<ref name=PGCH/> |
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| IDLH = 250 ppm<ref name=PGCH/> |
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| REL = TWA 2.3 ppm (10 mg/m<sup>3</sup>)<ref name=PGCH/> |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = ]s |
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| OtherFunction = ]: |
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* ] |
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* ]<br />], ] |
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}} |
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}} |
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}} |
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'''''ortho''-Cresol''' (] name: '''2-methylphenol''', also known as '''2-hydroxytoluene''' or '''''ortho''-Toluenol''') is an ] with the formula CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of ] and is an isomer of ] and ].<ref name=Ullmann>Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a08_025}}</ref> |
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'''''ortho''-Cresol''', also '''2-methylphenol''', is a ], with formula (CH<sub>3</sub>)C<sub>6</sub>H<sub>4</sub>(OH). |
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== Natural occurrences == |
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It is an isomer of ], ] and ] |
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''o''-Cresol is one of the chemical compounds found in ]. This compound is gathered from the beaver's castor glands and found in the white cedar consumed by the ].<ref>The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 ()</ref> |
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''o''-Cresol is a constituent of ].<ref>{{cite journal|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482|doi-access=free}}</ref> |
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==Chemistry== |
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'''Cresols''' are ]s which are ]]s. They are a widely occurring natural and manufactured group of ] ]s which are categorized as ] (sometimes called ''phenolics''). Depending on the ], cresols can be ] or ] because they have ]s not far from room temperature. Like other types of phenols, they are slowly ] by long exposure to ] and the impurities often give cresols a yellowish to brownish red tint. Cresols have an ] characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell. |
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== Production == |
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In its ], a cresol ] has a ] substituted onto the ] of a ] molecule. There are three forms of cresols that are only slightly different in their chemical structure: '''''ortho''-cresol''' (''o''-cresol), '''''meta''-cresol''' (]), and '''''para''-cresol''' (]). These forms occur separately or as a mixture. |
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Together with many other compounds, ''o''-cresol is traditionally extracted from ], the volatile materials obtained in the production of ] from ]. A similar source material is petroleum residues. These residue contains a few percent by weight of ] and isomeric ]s. In addition to the materials derived from these natural sources, about two thirds of the Western world's supply is produced by ] of phenol using ]. The ] is catalysed by metal oxides: |
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:C<sub>6</sub>H<sub>5</sub>OH + CH<sub>3</sub>OH → CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>OH + H<sub>2</sub>O |
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Over-methylation gives ]. Many other production methods have been examined, including oxidative decarboxylation of ], oxygenation of ], and hydrolysis of ].<ref name=Ullmann/> |
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== Applications == |
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== Applications == |
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''o''-Cresol is mainly used as a precursor to other compounds. ] and ] gives members of commercially important ]s, such as ] (MCPA). Nitration gives ], a popular herbicide. ] gives ], a pharmaceutical intermediate. ], essence of oregano, is derived by alkylation of ''o''-cresol with ]. The muscle relaxant ] is an ether derived from ''o''-cresol.<ref name=Ullmann/> |
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Cresols are used to ] other chemicals, as ]s and ]s, and to make specific chemicals that kill ] ]s. |
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== Health effects == |
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Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name ]. In the past, cresol solutions have been used as ]s in ], but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal ] in mid-twentieth century America<ref></ref>. |
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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 ] at very high levels, they can be harmful. Breathing high levels of cresols for a short time results in irritation of the ] and throat. Aside from these effects, very little is known about the effects of breathing cresols at lower levels over longer times. The acute ] for oral ingestion by mice is 344 mg/kg.<ref name=Ullmann/> |
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== References == |
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Cresols are found in many foods and in wood and ], ], ], and in brown mixtures such as ], ] and ]s, which are wood ]s. Small organisms in soil and water produce cresols when they break down materials in the environment. |
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{{reflist}} |
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== External links == |
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==Health effects== |
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* |
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Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the ] at very high levels, they can be very harmful. Effects observed in people include ] and burning of ], ]s, ], and ]; abdominal pain and vomiting; ] damage; ]; ] and ] damage; facial paralysis; ]; and ]. |
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* (accessed 22 December 2022) |
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Breathing high levels of cresols for a short time results in irritation of the ] and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times. |
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Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the ] and ]. |
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Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, ], and ]s. |
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Short-term and long-term studies with animals have shown similar effects from exposure to cresols. No human or animal studies have shown harmful effects from cresols on the ability to have children. |
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It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols. |
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==External links== |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Cresol, o-}} |
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{{DEFAULTSORT:Cresol, o-}} |
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