99-87-6

Basic information

• Product Name: p-Cymene
• Synonyms: p-Cymene(8CI);1-Isopropyl-4-methylbenzene;1-Methyl-4-(1-methylethyl)benzene;1-Methyl-4-isopropylbenzene;2-p-Tolylpropane;4-Cymene;4-Isopropyl-1-methylbenzene;4-Methylisopropylbenzene;Camphogen;Dolcymene;NSC 4162;p-Cymol;p-Isopropyltoluene;p-Methylcumene;p-Methylisopropylbenzene
• CAS NO: 99-87-6
• Molecular Formula: C10H14
• Molecular Weight: 134.21816
• EINECS: 202-796-7
• Mol File: 99-87-6.mol
• Article Data: 278

Chemical Properties

• Melting Point: -68℃
• Boiling Point: 173.9 °C at 760 mmHg
• Flash Point: 47.2 °C
• Appearance: colourless liquid with a characteristic odour
• Density: 0.861 g/cm³
• Refractive Index: 1.489-1.491
• Water Solubility: PRACTICALLY INSOLUBLE
• CAS DataBase Reference: p-Cymene(CAS DataBase Reference)
• NIST Chemistry Reference: p-Cymene(99-87-6)
• EPA Substance Registry System: p-Cymene(99-87-6)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R10:; R36/37/38:
• Safety Statements: S26:; S36:
• Hazardous Substances Data: 99-87-6(Hazardous Substances Data)

Usage

General Description

p-Cymene is a naturally occurring aromatic hydrocarbon found in various essential oils, particularly those of cumin and thyme. It is a colorless liquid with a characteristic scent and is commonly used in the production of fragrances, flavorings, and as a solvent in industrial applications. The chemical has been shown to possess antimicrobial, antifungal, and antiviral properties, making it useful in the pharmaceutical and healthcare industries. Additionally, p-Cymene has potential antioxidant and anti-inflammatory effects, leading to its investigation for potential therapeutic uses in the treatment of various conditions. Overall, p-Cymene is a versatile chemical with a range of industrial and medicinal applications.

InChI:InChI=1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3

Upstream product

• 64-17-5 ethanol 
• 34048-72-1 1,2,8-tribromo-p-menthane 
• 151-50-8 potassium cyanide 
• 4080-46-0 2⁽¹⁰⁾,3-pinadiene 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 6069-98-3 cis-1-isopropyl-4-methyl-cyclohexane 
• 57526-47-3 carane-3,4-diol 
• 498-15-7 (+)-Δ³-carene 
• 118-75-2 chloranil 
• 4497-92-1 2-carene 
• 64-19-7 acetic acid 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 60-29-7 diethyl ether 

Downstream Products

• 27805-39-6 (4-methoxyphenyl)(pyridin-2-yl)methanol 
• 27652-91-1 α-(2-methoxyphenyl)-2-pyridinemethanol 
• 93877-73-7 2-(5-isopropyl-2-methyl-benzoyl)-benzoic acid 
• 734-17-8 2,3-dimethyl-2,3-di-p-tolyl-butane 
• 6798-82-9 1-(5-isopropyl-2-methyl-phenyl)-dodecan-1-one 
• 3077-71-2 8-hydroperoxy-p-cymene 
• 111356-13-9 1-(3-chloro-propyl)-4-(5-isopropyl-2-methyl-benzyl)-benzene 
• 1153-36-2 1-(4-methylphenyl)-1,3,3,6-tetramethylindane 
• 99-82-1 Menthane 
• 1642-75-7 4,5,6,7-tetraphenyl-2,3,3a,7a-tetrahydro-indene 
• 108-31-6 maleic anhydride 
• 110-16-7 maleic acid 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 1195-32-0 1-methyl-4-isopropenylbenzene 

Relevant articles and documents

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Photooxidation of a conjugated diene by an exciplex mechanism: Amplification via radical chain reactions in the perylene diimide-photosensitized oxidation of α-terpinene

Irradiation of the perylene diimide (1) or 9,10-dicyanoanthracene (DCA) in the presence of α-terpinene (2-HH) in the presence of molecular oxygen leads to moderately efficient oxidation of 2-HH to p-cymene (2). Although 1 might be expected to photosensitize oxidations by the conventional "singlet oxygen pathways, spectroscopic studies indicate that while oxygen can quench the fluorescent singlet of 1, no singlet oxygen is produced. 2-HH is also an efficient quencher of the fluorescent singlets of 1 and DCA and, for nonpolar solvents such as methylene chloride, in each case the quenching results in formation of an exciplex or contact radical ion pair. Under conditions where quenching by 2-HH to form the exciplex is complete, maximum quantum yields of 2 are obtained, thus indicating that the exciplex is the precursor to its formation. Nonproductive decay of the exciplex to starting materials is its major fate, thus the moderately high quantum efficiencies for formation of 2 require a mechanism involving amplification. Spin-trapping experiments suggest the role of hydroperoxy radicals and amplification by a radical chain mechanism involving these radicals and the intermediate 2-H. is proposed. Possible paths for reaching these radicals from the exciplex are considered; either oxygen quenching of the exciplex or proton transfer within the exciplex followed by oxygen interception of the semireduced perylene diimide appear viable. For the reaction of DCA with 2-HH and oxygen, it is found that the much longer-lived exciplex undergoes quenching by oxygen.

The conversion of 1,8-cineole sourced from renewable Eucalyptus oil to p-cymene over a palladium doped γ-Al2O3 catalyst

The conversion of 1,8-cineole, sourced from the steam distillation of Eucalyptus waste, to p-cymene has been studied. Both alumina and palladium on alumina have been found to be active catalysts, the latter producing p-cymene in near quantitative conversion. Catalyst testing coupled with catalyst characterisation showed the catalysts to be multifunctional, promoting dehydration, dehydrogenation and isomerisation in a one step process.

Deactivation of a ruthenium(II) N-heterocyclic carbene p-cymene complex during transfer hydrogenation catalysis

A ruthenium (II) N-heterocyclic carbene (NHC) complex was synthesized to investigate ligand dissociation as a possible deactivation pathway for the catalytic cycle of a transfer hydrogenation reaction. Diiodo(1,3-dimethylbenzimidazole-2-ylidene)(p-cymene)ruthenium(II) was synthesized for use as the catalytic species and characterized using physico-chemical, spectroscopic methods, and single crystal X-ray diffraction. The transfer of hydrogen from isopropanol to acetophenone was followed using 1H NMR. We observed 94% conversion of the substrate to the alcohol product after 1?h. We also found that the p-cymene complex decomposed during the catalytic reaction to the extent of 80% deactivation after 1?h, based on 1H NMR spectrometry. From Gaussian calculations, an ultraviolet–visible spectrum that is in excellent agreement with the actual spectrum was computed, giving insight into the nature of the absorptions observed experimentally.

Alkylation of Toluene with Isopropanol on Lantanum Modified ZSM-5 Zeolite

Abstract: The effect of lanthanum concentration on the physicochemical and catalyticproperties of HZSM-5 zeolite in a reaction of toluene alkylation withisopropanol was studied in a temperature range of 250–350°C. Based on the dataobtained by X-ray diffraction analysis, low-temperature nitrogen adsorption (BETmethod), and IR spectroscopy, it was shown that an increase in lanthanumconcentration in HZSM-5 from 1.0 wt % to 7.0 wt % reduces both the specificsurface area and the pore volume of the zeolite despite the retention of itscrystalline structure. This also results in redistribution of acid sites,specifically decreases the concentration of strong Br?nsted acid sites (B) andincreases that of moderate Lewis acid sites (L), thus decreasing the B/L ratiofrom 3.53 to 0.20. All these occurrences have a crucial effect on theselectivity of reaction products and, in particular, on the p-isopropyl toluene (4-IPT) selectivity. Maximumselectivity, making up 72.4%, is achieved by a zeolite containing 5.0 wt %lanthanum at a B/L ratio of 0.25.

Singlet-Oxygen Generation by Peroxidases and Peroxygenases for Chemoenzymatic Synthesis

Singlet oxygen is a reactive oxygen species undesired in living cells but a rare and valuable reagent in chemical synthesis. We present a fluorescence spectroscopic analysis of the singlet-oxygen formation activity of commercial peroxidases and novel peroxygenases. Singlet-oxygen sensor green (SOSG) is used as fluorogenic singlet oxygen trap. Establishing a kinetic model for the reaction cascade to the fluorescent SOSG endoperoxide permits a kinetic analysis of enzymatic singlet-oxygen formation. All peroxidases and peroxygenases show singlet-oxygen formation. No singlet oxygen activity could be found for any catalase under investigation. Substrate inhibition is observed for all reactive enzymes. The commercial dye-decolorizing peroxidase industrially used for dairy bleaching shows the highest singlet-oxygen activity and the lowest inhibition. This enzyme was immobilized on a textile carrier and successfully applied for a chemical synthesis. Here, ascaridole was synthesized via enzymatically produced singlet oxygen.

Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions

Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.