Cannabis Indica

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→‎Isomers and production: wikilink to m-Cymene, ref fix
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m added refractive index value
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{{redirect|Cymene|the other isomers|Cymenes|the ancient city of Thessaly|Cymene (Thessaly)}}
{{redirect|Cymene|the other isomers|Cymenes|the ancient city of Thessaly|Cymene (Thessaly)}}
{{chembox
{{chembox
| verifiedrevid = 414093009
| verifiedrevid = 414093009
| Name = ''p''-Cymene
| Name = ''p''-Cymene
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = P-Cymol.svg
| ImageFileL1 = P-Cymol.svg
| ImageNameL1 = Skeletal formula
| ImageNameL1 = Skeletal formula
| ImageFileR1 = Cymene-3D-balls.png
| ImageFileR1 = Cymene-3D-balls.png
| ImageNameR1 = Ball-and-stick model
| ImageNameR1 = Ball-and-stick model
| 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 = [[Royal_Society_of_Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 139, 597 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| 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 = [[Royal_Society_of_Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 139, 597 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| OtherNames = ''para''-Cymene<br />4-Isopropyltoluene<br />4-Methylcumene<br />Paracymene
| OtherNames = ''para''-Cymene<br />4-Isopropyltoluene<br />4-Methylcumene<br />Paracymene
|Section1={{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7183
| ChemSpiderID = 7183
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| InChI = 1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
| InChI = 1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
}}
}}
|Section2={{Chembox Properties
| Section2 = {{Chembox Properties
| C=10 | H=14
| C=10 | H=14
| Density = 0.857 g/cm<sup>3</sup>
| Density = 0.857 g/cm<sup>3</sup>
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| Appearance = Colourless liquid
| Appearance = Colourless liquid
| MagSus = {{val|-1.028|e=-4|u=cm<sup>3</sup>/mol}}
| MagSus = {{val|-1.028|e=-4|u=cm<sup>3</sup>/mol}}
| RefractIndex = 1.4908 (at 20&nbsp;°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=[[The Journal of Chemical Physics]]|language=en|date=December 2022|volume=157|issue=24|pages=244501|doi=10.1063/5.0133511}}</ref>

}}
}}
|Section3={{Chembox Hazards
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS08}}{{GHS09}}
| GHSPictograms = {{GHS02}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| GHSSignalWord = Danger

Revision as of 19:15, 1 January 2023

"Cymene" redirects here. For the other isomers, see Cymenes. For the ancient city of Thessaly, see Cymene (Thessaly).
p-Cymene
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
1-Methyl-4-(propan-2-yl)benzene[1]
Other names
para-Cymene
4-Isopropyltoluene
4-Methylcumene
Paracymene
Identifiers
3D model (JSmol)
3DMet
1903377
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.542 Edit this at Wikidata
EC Number
  • 202-796-7
305912
KEGG
RTECS number
  • GZ5950000
UNII
UN number 2046
  • InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 checkY
    Key: HFPZCAJZSCWRBC-UHFFFAOYSA-N checkY
  • InChI=1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
    Key: HFPZCAJZSCWRBC-UHFFFAOYAD
  • c1cc(ccc1C(C)C)C
Properties
C10H14
Molar mass 134.222 g·mol−1
Appearance Colourless liquid
Density 0.857 g/cm3
Melting point −68 °C (−90 °F; 205 K)
Boiling point 177 °C (351 °F; 450 K)
23.4 mg/L
−1.028×10−4 cm3/mol
1.4908 (at 20 °C) [2]
Hazards
GHS labelling:
GHS02: FlammableGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H304, H411
P210, P233, P240, P241, P242, P243, P273, P280, P301+P310, P303+P361+P353, P331, P370+P378, P391, P403+P235, P405, P501
Flash point 47 °C (117 °F; 320 K)
435 °C (815 °F; 708 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

p-Cymene is a naturally occurring aromatic organic compound. It is classified as an alkylbenzene related to a monoterpene. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. p-Cymene is insoluble in water, but miscible with organic solvents.

Isomers and production

In addition to p-cymene, two less common geometric isomers are 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, as expected from the terpene rule. All three isomers form the group of cymenes.

Cymene is also produced by alkylation of toluene with propylene.[3]

Related compounds

It is a constituent of a number of essential oils, most commonly the oil of cumin and thyme. Significant amounts are formed in sulfite pulping process from the wood terpenes.

p-Cymene is a common ligand for ruthenium. The parent compound is [(η6-cymene)RuCl2]2. This half-sandwich compound is prepared by the reaction of ruthenium trichloride with the terpene α-phellandrene. The osmium complex is also known.[4]

Hydrogenation gives the saturated derivative p-menthane.

References

  1. ^ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 139, 597. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Pabst, Florian; Blochowicz, Thomas (December 2022). "On the intensity of light scattered by molecular liquids - Comparison of experiment and quantum chemical calculations". The Journal of Chemical Physics. 157 (24): 244501. doi:10.1063/5.0133511.
  3. ^ Vora, Bipin V.; Kocal, Joseph A.; Barger, Paul T.; Schmidt, Robert J.; Johnson, James A. (2003). "Alkylation". Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961.
  4. ^ Bennett, M. A.; Huang, T.-N.; Matheson, T. W.; Smith, A. K. (1982). "(η6-Hexamethylbenzene)Ruthenium Complexes". Inorganic Syntheses. 21: 74–78. doi:10.1002/9780470132524.ch16.


source: https://en.wikipedia.org/w/index.php?title=P-Cymene&diff=prev&oldid=1130940798

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