P-cymene

p-Cymene

Names

Preferred IUPAC name

1-Methyl-4-(propan-2-yl)benzene

Other names

p-Cymene (no longer recommended)
4-Isopropyltoluene
4-Methylcumene
Paracymene

Identifiers

CAS Number

99-87-6^Y

3D model (Jmol)

Interactive image

ChEBI

CHEBI:28768

ChemSpider

7183^Y

202-796-7

C06575^Y

PubChem CID

7463

UNII

1G1C8T1N7Q^Y

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

SMILES

c1cc(ccc1C(C)C)C

Properties

Chemical formula

C₁₀H₁₄

Molar mass

134.21 g/mol

Appearance

Colourless liquid

Density

0.857 g/cm³

Melting point

−68 °C (−90 °F; 205 K)

Boiling point

177 °C (351 °F; 450 K)

Solubility in water

23.4 mg/L

Magnetic susceptibility (χ)

-102.8·10⁻⁶ cm³/mol

Hazards

47 °C (117 °F; 320 K)

Autoignition
temperature

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).

(what is ^YN ?)

Infobox references

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. 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. All three isomers form the group of cymenes.

p-Cymene is insoluble in water, but miscible with ethanol and diethyl ether.

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.

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