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

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 5989-27-5 D-limonene 
• 512-85-6 ascaridole 
• 60-29-7 diethyl ether 
• 75-16-1 methylmagnesium bromide 
• 89-81-6 piperitone 
• 4221-98-1 (R)-5-isopropyl-2-methylcyclohexa-1,3-diene 
• 1196-00-5 d,l-Isopinocamphenol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 31383-92-3 6-bromo-p-menth-1-ene 
• 563-34-8 α-thujene 
• 76-22-2 Camphor 
• 586-62-9 Terpinolene 

Downstream Products

• 39694-88-7 4-(5-isopropyl-2-methyl-phenyl)-4-oxo-butyric acid 
• 27805-39-6 (4-methoxyphenyl)(pyridin-2-yl)methanol 
• 27652-91-1 α-(2-methoxyphenyl)-2-pyridinemethanol 
• 5663-25-2 4-methyl-4-p-tolyl-[1,3]dioxane 
• 1866-01-9 5-isopropyl-2-methylbenzyl chloride 
• 100575-43-7 bis-(5-isopropyl-2-methyl-phenyl)-methane 
• 734-17-8 2,3-dimethyl-2,3-di-p-tolyl-butane 
• 6798-82-9 1-(5-isopropyl-2-methyl-phenyl)-dodecan-1-one 
• 101286-83-3 3-ethyl-5-(5-isopropyl-2-methyl-benzylidene)-2-thioxo-thiazolidin-4-one 
• 1460-98-6 1,3-di-isopropyl-4-methylbenzene 
• 4237-70-1 4-(1,1-dimethylpropyl)toluene 
• 22975-62-8 1-isopropyl-4-propyl-benzene 
• 101740-99-2 4-(5-isopropyl-2-methyl-phenyl)-valeric acid ethyl ester 
• 3077-71-2 8-hydroperoxy-p-cymene 

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.

Radical induced disproportionation of alcohols assisted by iodide under acidic conditions

The disproportionation of alcohols without an additional reductant and oxidant to simultaneously form alkanes and aldehydes/ketones represents an atom-economical transformation. However, only limited methodologies have been reported, and they suffer from a narrow substrate scope or harsh reaction conditions. Herein, we report that alcohol disproportionation can proceed with high efficiency catalyzed by iodide under acidic conditions. This method exhibits high functional group tolerance including aryl alcohol derivatives with both electron-withdrawing and electron-donating groups, furan ring alcohol derivatives, allyl alcohol derivatives, and dihydric alcohols. Under the optimized reaction conditions, a 49% yield of 5-methyl furfural and a 49% yield of 2,5-diformylfuran were obtained simultaneously from 5-hydroxymethylfurfural. An initial mechanistic study suggested that the hydrogen transfer during this redox disproportionation occurred through the inter-transformation of HI and I2. Radical intermediates were involved during this reaction.

Mesoporous tin phosphate as an effective catalyst for fast cyclodehydration of bio-based citral into p-cymene

Effective synthesis of aromatic compounds from renewable biomass is highly important yet challenging. p-Cymene is an attractive aromatic compound with various promising applications in the manufacture of fine chemicals. In this study, a novel and effective catalytic system based on mesoporous tin phosphate (M-SnPO) with Lewis-Br?nsted dual acidity was developed for the fast synthesis of p-cymene from the cyclodehydration of bio-based citral. Up to 78.5% yield of p-cymene was achieved from the cyclodehydration of citral at 180 °C within only 0.5 h, superior to the results reported for benchmark homogeneous acid catalysts. Characterization of as-prepared M-SnPO catalyst via various techniques indicates that the synergic effect of Lewis and Br?nsted acidic sites, large pore-sized structure, and high surface area are responsible for its remarkable catalytic performance. In addition, the effectiveness of the M-SnPO catalyst could be almost sustained over multiple cycles without significant loss. The work herein is the first example of developing a Lewis-Br?nsted dual acidic heterogeneous catalyst for the fast synthesis of p-cymene from the cyclodehydration of citral.