Cymene

Cymene: Cymene

IUPAC name

1-Methyl-4-(1-methylethyl)benzene

Other names

4-Isopropyltoluene; Paracymene

Identifiers

CAS number 99-87-6^Y

PubChem 7463

ChemSpider 7183^Y

UNII 1G1C8T1N7Q^Y

EC number 202-796-7

KEGG C06575^Y

ChEBI CHEBI:28768

ChEMBL CHEMBL442915^Y

Jmol-3D images Image 1

SMILES

c1cc(ccc1C(C)C)C

InChI

InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3^Y
Key: HFPZCAJZSCWRBC-UHFFFAOYSA-N^Y
InChI=1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
Key: HFPZCAJZSCWRBC-UHFFFAOYAD

Properties

Molecular formula C₁₀H₁₄

Molar mass 134.21 g/mol

Appearance Colourless liquid

Density 0.857 g/cm³

Melting point
-68°C

Boiling point
177°C

Solubility in water Negligible

Hazards

R-phrases R10

S-phrases S16

Flash point 47°C

Autoignition
temperature 435°C

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Cymene, or p-cymene, is a naturally occurring aromatic organic compound. It is classified as a hydrocarbon related to a monoterpene. 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 ethanol and ether.

Cymene is a constituent of a number of essential oils, most commonly the oil of cumin and thyme.

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.

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.^[1]

Significant amounts of cymene are formed in sulfite pulping process from the wood terpenes.

References

^ Bennett, M. A.; Huang, T. N.; Matheson, T. W. and Smith, A. K. (1982). "(h6-Hexamethylbenzene)ruthenium complexes". Inorganic Syntheses 21: 74–8. doi:10.1002/9780470132524.ch16.

Categories:
Flavors
Alkylbenzenes
Monoterpenes

Cymene

IUPAC name 1-Methyl-4-(1-methylethyl)benzene
Other names 4-Isopropyltoluene; Paracymene
Identifiers
CAS number	99-87-6^Y
PubChem	7463
ChemSpider	7183^Y
UNII	1G1C8T1N7Q^Y
EC number	202-796-7
KEGG	C06575^Y
ChEBI	CHEBI:28768
ChEMBL	CHEMBL442915^Y
Jmol-3D images	Image 1
SMILES c1cc(ccc1C(C)C)C
InChI InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3^Y Key: HFPZCAJZSCWRBC-UHFFFAOYSA-N^Y InChI=1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 Key: HFPZCAJZSCWRBC-UHFFFAOYAD
Properties
Molecular formula	C₁₀H₁₄
Molar mass	134.21 g/mol
Appearance	Colourless liquid
Density	0.857 g/cm³
Melting point	-68°C
Boiling point	177°C
Solubility in water	Negligible
Hazards
R-phrases	R10
S-phrases	S16
Flash point	47°C
Autoignition temperature	435°C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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cymène — [simɛn] n. m. ÉTYM. D. i.; du lat. cyma, et suff. ène. ❖ ♦ Chim. Paraméthylisopropylbenzène, de formule CH3–C6H4–CH(CH3)2. || Le cymène, qui peut s extraire d essences de fruits (ombellifères) possède des propriétés pharmaceutiques… … Encyclopédie Universelle
Cymene — Cy mene (s? m?n), n. (Chem.) A colorless, liquid, combustible hydrocarbon, {CH3.C6H4.C3H7}, of pleasant odor, obtained from oil of cumin, oil of caraway, carvacrol, camphor, etc.; called also {paracymene}, and formerly {camphogen}. [1913 Webster] … The Collaborative International Dictionary of English
cymene — [sī′mēn΄] n. [< Gr kyminon: see CUMIN] a colorless hydrocarbon, CH3C6H4CH(CH3) 2, occurring in three isomeric forms ( orthocymene, metacymene, and paracymene), derived from toluene: the most common form, paracymene, is found in the oil of… … English World dictionary
cymene — /suy meen/, n. a colorless, pleasant smelling benzene derivative, C10H14, occurring in the volatile oil of the common cumin, Cuminum cyminum, and existing in three forms, the ortho, meta, and para isomers. Cf. para cymene. [1860 65; < Gk… … Universalium
cymene — /ˈsaɪmin/ (say suymeen) noun an unsaturated, terpene hydrocarbon, C10H14, with a pleasant smell, occurring in the volatile oil of the common cumin, Cuminum cyminum, and existing in three isomeric forms, ortho , meta , and para cymene. {cym… …
cymene — cimenas statusas T sritis chemija formulė CH₃C₆H₄CH(CH₃)₂ atitikmenys: angl. cymene rus. цимен; цимол ryšiai: sinonimas – 1 izopropil 4 metilbenzenas … Chemijos terminų aiškinamasis žodynas
(Cymene)ruthenium dichloride dimer — Other names Dichloro(p cymene)ruthenium(II) dimer … Wikipedia
cymene — noun any of several isomeric naturally occurring terpenoid hydrocarbons; a constituent of a number of essential oils, most commonly the oil of cumin and thyme … Wiktionary
cymene — cy·mene … English syllables
cymene — noun any of three isotopes of a colorless aromatic liquid hydrocarbon occurring in the volatile oil of cumin and thyme and used in the manufacture of synthetic resins • Hypernyms: ↑hydrocarbon … Useful english dictionary

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Cymene

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