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{{DISPLAYTITLE:''p''-Cymene}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 401603209 |
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|verifiedrevid = 414093009 |
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| Name = Cymene |
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|Name = ''p''-Cymene |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = P-Cymol.svg |
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|ImageFileL1 = P-Cymol.svg |
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| ImageSizeL1 = 120px |
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| ImageNameL1 = Skeletal formula |
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|ImageNameL1 = Skeletal formula |
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|ImageFileR1 = Cymene-3D-balls.png |
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| ImageSizeR1 = 110px |
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|ImageNameR1 = Ball-and-stick model |
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| ImageFileR1 = Cymene-3D-balls.png |
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|PIN = 1-Methyl-4-(propan-2-yl)benzene<ref>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = 139, 597 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| ImageNameR1 = Ball-and-stick model |
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|OtherNames = ''para''-Cymene<br />4-Isopropyltoluene<br />4-Methylcumene<br />Paracymene |
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| IUPACName = 1-Methyl-4-(1-methylethyl)benzene |
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|Section1 = {{Chembox Identifiers |
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| OtherNames = 4-Isopropyltoluene; Paracymene |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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|ChemSpiderID = 7183 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID = 7183 |
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|UNII = 1G1C8T1N7Q |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1G1C8T1N7Q |
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|RTECS = GZ5950000 |
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| KEGG = C06575 |
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|UNNumber = 2046 |
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|Gmelin = 305912 |
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| InChIKey = HFPZCAJZSCWRBC-UHFFFAOYAD |
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|Beilstein = 1903377 |
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| ChEMBL = 442915 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG = C06575 |
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| StdInChI = 1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 |
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|InChIKey = HFPZCAJZSCWRBC-UHFFFAOYAD |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChIKey = HFPZCAJZSCWRBC-UHFFFAOYSA-N |
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| CASNo = 99-87-6 |
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|ChEMBL = 442915 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 |
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| EINECS = 202-796-7 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| PubChem = 7463 |
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|StdInChIKey = HFPZCAJZSCWRBC-UHFFFAOYSA-N |
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| SMILES = c1cc(ccc1C(C)C)C |
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|CASNo = 99-87-6 |
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| InChI = 1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|EINECS = 202-796-7 |
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|PubChem = 7463 |
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|ChEBI = 28768 |
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|3DMet = B00975 |
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|SMILES = c1cc(ccc1C(C)C)C |
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|InChI = 1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 |
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}} |
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|Section2 = {{Chembox Properties |
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|C=10 | H=14 |
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|Density = 0.857 g/cm<sup>3</sup> |
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|MeltingPtC = -68 |
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|BoilingPtC = 177 |
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|Solubility = 23.4 mg/L |
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|Appearance = Colourless liquid |
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|MagSus = {{val|-1.028|e=-4|u=cm<sup>3</sup>/mol}} |
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|RefractIndex = 1.4908 (at 20 °C) <ref>{{cite journal|author1=Pabst, Florian|author2=Blochowicz, Thomas |title=On the intensity of light scattered by molecular liquids - Comparison of experiment and quantum chemical calculations|journal=]|language=en|date=December 2022|volume=157|issue=24|pages=244501|doi=10.1063/5.0133511|pmid=36586992 |bibcode=2022JChPh.157x4501P |doi-access=free}}</ref> |
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}} |
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|Section3 = {{Chembox Hazards |
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|GHSPictograms = {{GHS02}}{{GHS08}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|226|304|411}} |
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|PPhrases = {{P-phrases|210|233|240|241|242|243|273|280|301+310|303+361+353|331|370+378|391|403+235|405|501}} |
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|FlashPtC = 47 |
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|AutoignitionPtC = 435 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>14</sub> |
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| MolarMass = 134.21 g/mol |
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| Density = 0.857 g/cm<sup>3</sup> |
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| MeltingPt = -68°C |
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| BoilingPt = 177°C |
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| Solubility = Negligible |
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| Appearance = Colourless liquid |
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}} |
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| Section3 = {{Chembox Hazards |
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| SPhrases = {{S16}} |
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| RPhrases = {{R10}} |
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| FlashPt = 47°C |
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| Autoignition = 435°C |
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}} |
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}} |
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}} |
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'''Cymene''', or '''''p''-cymene''', is a naturally occurring ] ]. It is classified as a ] related to a ]. Its structure consists of a benzene ring ''para''-substituted with a methyl group and an isopropyl group. It is insoluble in water, but miscible with ] and ]. |
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'''''p''-Cymene''' is a naturally occurring ] ]. It is classified as an ] related to monocyclic ]s.<ref>{{cite journal |last=Balahbib |first=Abdelaali |last2=El Omari |first2=Nasreddine |last3=Hachlafi |first3=Naoufal EL. |last4=Lakhdar |first4=Fatima |last5=El Menyiy |first5=Naoual |last6=Salhi |first6=Najoua |last7=Mrabti |first7=Hanae Naceiri |last8=Bakrim |first8=Saad |last9=Zengin |first9=Gokhan |last10=Bouyahya |first10=Abdelhakim |date=2021-07-01 |title=Health beneficial and pharmacological properties of p-cymene |url=https://www.sciencedirect.com/science/article/abs/pii/S0278691521002921#:~:text=p%2Dcymene%20also%20known%20as,of%20terpenes%2C%20especially%20monocyclic%20monoterpenes. |journal=Food and Chemical Toxicology |volume=153 |pages=112259 |doi=10.1016/j.fct.2021.112259 |issn=0278-6915}}</ref> Its structure consists of a ] ring ] with a ] and an ]. ''p''-Cymene is insoluble in water, but miscible with ]s. |
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==Isomers and production== |
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Cymene is a constituent of a number of ]s, most commonly the oil of ] and ]. |
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In addition to ''p''-cymene, two less common geometric isomers are ], in which the alkyl groups are ''ortho''-substituted, and ], in which they are ''meta''-substituted. ''p''-Cymene is the only natural isomer, as expected from the ]. All three isomers form the group of ]. |
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Cymene is also produced by ] of ] with ].<ref>{{cite encyclopedia|title=Alkylation|first1=Bipin V.|last1=Vora|first2=Joseph A.|last2=Kocal|first3=Paul T.|last3=Barger|first4=Robert J.|last4=Schmidt|first5=James A.|last5=Johnson|year=2003|encyclopedia=Kirk‐Othmer Encyclopedia of Chemical Technology|doi=10.1002/0471238961.0112112508011313.a01.pub2|isbn=0471238961}}</ref> |
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There are two less common geometric isomers. ''o''-Cymene, in which the alkyl groups are ''ortho''-substituted, and ''m''-cymene, in which they are ''meta''-substituted. ''p''-Cymene is the only natural isomer. |
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==Related compounds== |
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Cymene is a common ligand for ruthenium. The parent compound is <sub>2</sub>]]. This ] is prepared by the reaction of ] with the terpene α-]. The osmium complex is also known.<ref>{{cite journal | author = Bennett, M. A.; Huang, T. N.; Matheson, T. W. and Smith, A. K. | title = (h6-Hexamethylbenzene)ruthenium complexes | journal = ] | year = 1982 | volume = 21 | pages = 74–8 | doi = 10.1002/9780470132524.ch16}}</ref> |
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It is a constituent of a number of ]s, most commonly the oil of ] and ]. Significant amounts are formed in sulfite pulping process from the wood terpenes. |
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''p''-Cymene is a common ligand for ]. The parent compound is <sub>2</sub>]]. This ] is prepared by the reaction of ] with the terpene α-]. The ] complex is also known.<ref>{{cite journal |first1=M. A. |last1=Bennett |first2=T.-N. |last2=Huang |first3=T. W. |last3=Matheson |first4=A. K. |last4=Smith | title = (''η''<sup>6</sup>-Hexamethylbenzene)Ruthenium Complexes | journal = ] | year = 1982 | volume = 21 | pages = 74–78 | doi = 10.1002/9780470132524.ch16|isbn=9780470132524 }}</ref> |
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Significant amounts of cymene are formed in sulfite pulping process from the wood terpenes. |
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Hydrogenation gives the saturated derivative ]. |
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==References== |
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== References == |
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<references/> |
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<references/> |
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{{DEFAULTSORT:Cymene, p-}} |
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{{Hydrocarbons}} |
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