6196-95-8

Basic information

• Product Name: 1,2-DIMETHYL-4-(1-PHENYL-ETHYL)-BENZENE
• Synonyms: 1,2-DIMETHYL-4-(1-PHENYL-ETHYL)-BENZENE;4-(1-phenylethyl)-o-xylene;Phenyl-o-xylylethane (POXE);Benzene, 1,2-dimethyl-4-(1-phenylethyl)-;phenyl-1-(3,4-dimethyl)phenylethane;1-PHENYL-1-XYLYLETHANE;1-Phenyl-1-(3,4-xylyl)-ethane;Phenylxylylethane: (PXE)
• CAS NO: 6196-95-8
• Molecular Formula: C₁₆H₁₈
• Molecular Weight: 210.31412
• EINECS: 228-249-2
• Mol File: 6196-95-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: -56 °C
• Boiling Point: 306.4 °C at 760 mmHg
• Flash Point: 143 °C
• Appearance: Colorless/Liquid
• Density: 0.961 g/cm³
• Vapor Pressure: 0.0014mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 1,2-DIMETHYL-4-(1-PHENYL-ETHYL)-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIMETHYL-4-(1-PHENYL-ETHYL)-BENZENE(6196-95-8)
• EPA Substance Registry System: 1,2-DIMETHYL-4-(1-PHENYL-ETHYL)-BENZENE(6196-95-8)

Safety Data

• Hazardous Substances Data: 6196-95-8(Hazardous Substances Data)

Usage

General Description

1,2-Dimethyl-4-(1-phenyl-ethyl)-benzene is a chemical compound that falls under the category of aromatic hydrocarbons. The structure of this compound includes a benzene ring, which is a six-carbon ring with alternating double bonds, substituted with two methyl groups and a phenylethyl group. This means that two of the hydrogen atoms in the benzene ring are replaced by methyl (CH3) groups and one other is replaced by a phenylethyl group. Due to the presence of the benzene ring, this compound could potentially exhibit characteristics common to aromatic compounds, like stability, reactivity under specific conditions, and ability to undergo electrophilic substitution reactions. Its specific applications, hazards, and handling procedures depend largely on its physical and chemical properties and may vary accordingly.

InChI:InChI=1/C16H18/c1-12-9-10-16(11-13(12)2)14(3)15-7-5-4-6-8-15/h4-11,14H,1-3H3

Synthetic route

o-xylene (95-47-6) + bis(1-phenylethyl)ether (93-96-9) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With iron(III) chloride; chloro-trimethyl-silane In 1,2-dichloro-ethane at 20℃; for 0.166667h; Friedel-Crafts Alkylation; Inert atmosphere;	100%

styrene (100-42-5) + o-xylene (95-47-6) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With cross-linked poly acidic ionic liquids In N,N-dimethyl-formamide at 120℃; for 3h; Solvent; Temperature; High pressure;	99.67%
With phosphotungstic acid at 120℃; for 3h; Reagent/catalyst;	98.3%
With 12-tungstophosphoric acid supported 30percent triethylammonium acetate, P123 in micro/mesoporous silica at 119.84℃; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Friedel-Crafts Alkylation;	93.8%

styrene (100-42-5) + o-xylene (95-47-6) → 1,2-dimethyl-2-(1-phenylethyl)benzene (81749-28-2) + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With immobilized 30percent 12-tungstophosphoric acid-imidazole(1H)-3-ium-3-triethoxysilylpropyl-1-(propyl-3-sulfonate) on mesoporous silica SBA-15 at 120℃; for 3h; Reagent/catalyst;	A n/a B 93.9%
With iron(III) chloride at 80℃; for 4h;
With SiO2-supported InCl2 at 80℃; for 3h;
With gold(III) chloride; silver hexafluoroantimonate In 1,2-dichloro-ethane at 50℃; for 5h; Inert atmosphere; Darkness; regioselective reaction;
With aminosilane-modified lanthanum-substituted mesoporous silica-supported phosphotungstic acid at 120℃; for 3h; regioselective reaction;

o-xylene (95-47-6) + tert-butyldimethyl(1-phenylethoxy)silane (92976-56-2) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 2.5h; Friedel-Crafts Alkylation; Inert atmosphere; regioselective reaction;	93%

o-xylene (95-47-6) + 1-phenyl-1-trimethylsilyloxyethane (14856-75-8) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 1h; Reagent/catalyst; Time; Friedel-Crafts Alkylation; Inert atmosphere; regioselective reaction;	92%

o-xylene (95-47-6) + triethyl(1-phenylethoxy)silane (112473-30-0, 18442-52-9) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 1.5h; Friedel-Crafts Alkylation; Inert atmosphere; regioselective reaction;	91%

o-xylene (95-47-6) + 1-Phenylethanol (98-85-1, 13323-81-4) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
[Ir2(COD)2(SnCl3)2(Cl)2)(μ-Cl)2] In 1,2-dichloro-ethane at 80℃; for 12h;	89%
With 2,3,4,5-tetrafluorophenyl(dihydroxy)borane In nitromethane at 20℃; for 1h; Friedel-Crafts Alkylation;	88%
With triphenylphosphine ditriflate In dichloromethane at 20℃; for 1h; Friedel-Crafts benzylation;	79%

o-xylene (95-47-6) + (1-nitroethyl)benzene (7214-61-1) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With tin(IV) chloride for 1h; Ambient temperature;	65%

o-xylene (95-47-6) + bis(1-phenylethyl)ether (93-96-9) → 1-Phenylethanol (98-85-1, 13323-81-4) + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With iron(III) chloride; Hexamethyldisiloxane In 1,2-dichloro-ethane at 20℃; for 0.5h; Friedel-Crafts Alkylation; Inert atmosphere;	A 14% B 22%
With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 0.5h; Friedel-Crafts Alkylation; Inert atmosphere;	A 11% B 9%

styrene (100-42-5) + o-xylene (95-47-6) → 1,3-diphenyl-1-(o-xylyl)butane (56525-86-1) + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With toluene-4-sulfonic acid; hydroquinone at 110℃; for 11.5h; Yield given. Yields of byproduct given;

o-xylene (95-47-6) + 1-phenylethyl acetate (93-92-5, 50373-55-2) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With dihydrogen hexachloroplatinate at 80℃; for 1h; Friedel-Crafts alkylation;	99 % Chromat.
gold(III) chloride In nitromethane at 80℃; for 20h; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures; Friedel-Crafts reaction;	99 % Chromat.
With iron(III) chloride at 50℃; for 20h; Friedel-Crafts alkylation;	99 % Chromat.
With 1-butyl-3-methylimidazolium tetrachloridoferrate(III) at 80℃; for 12h; Friedel-Crafts type benzylation; regioselective reaction;	98 %Chromat.

o-xylene (95-47-6) + 1-Phenylethanol (98-85-1, 13323-81-4) → 1,2-dimethyl-2-(1-phenylethyl)benzene (81749-28-2) + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With iron(III) chloride at 80℃; for 24h; Friedel-Crafts alkylation;

o-xylene (95-47-6) + 1-Phenylethanol (98-85-1, 13323-81-4) → 1,3-diphenyl-1-butene (7614-93-9) + 1,2-dimethyl-2-(1-phenylethyl)benzene (81749-28-2) + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate at 100℃; for 1h; Friedel-Crafts-type benzylation;

styrene (100-42-5) + o-xylene (95-47-6) → 1,3-diphenyl-1-butene (7614-93-9) + 1,2-dimethyl-2-(1-phenylethyl)benzene (81749-28-2) + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With iodine at 130℃; for 2h; Friedel-Crafts Reaction;

1-Phenylethanol (98-85-1, 13323-81-4) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 - 20 °C 2: 1-butyl-3-methylimidazolium tetrachloridoferrate(III) / 12 h / 80 °C View Scheme

1-phenyl-1-trimethylsilyloxyethane (14856-75-8) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: o-xylene; iron(III) chloride / 1,2-dichloro-ethane / 0.12 h / 20 °C / Inert atmosphere 2: iron(III) chloride; chloro-trimethyl-silane / 1,2-dichloro-ethane / 0.17 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: o-xylene; iron(III) chloride / 1,2-dichloro-ethane / 0.12 h / 20 °C / Inert atmosphere 2: iron(III) chloride; Hexamethyldisiloxane / 1,2-dichloro-ethane / 0.5 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: o-xylene; indium(III) chloride / 1,2-dichloro-ethane / 3 h / 20 °C / Inert atmosphere 2: iron(III) chloride / 1,2-dichloro-ethane / 6 h / 20 °C / Inert atmosphere View Scheme

o-xylene (95-47-6) + 1-phenyl-1-trimethylsilyloxyethane (14856-75-8) → bis(1-phenylethyl)ether (93-96-9) + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 3h; Inert atmosphere;	A 58 %Spectr. B 42 %Spectr.

(3,4-dimethylphenyl)(phenyl)methanone (2571-39-3) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: -78 - 20 °C 2.1: (di-p-tolylmethyl)triethylsilane; C18H15FP(1+)*C24H20B(1-); bromobenzene-d5 / 24 h / 100 °C / 3040.2 Torr / Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen View Scheme

1-phenyl-1-(3,4-dimethylphenyl)ethylene (38112-01-5) → 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With bromobenzene-d5; (di-p-tolylmethyl)triethylsilane; C18H15FP(1+)*C24H20B(1-) at 100℃; under 3040.2 Torr; for 24h; Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen;

styrene (100-42-5) + o-xylene (95-47-6) → bis(1-phenyl ethanyl)orthoxylene + 1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8)

Conditions	Yield
With aluminum (III) chloride; 1-n-butyl-3-methylimidazolim bromide at 30℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Overall yield = 98 %Chromat.;

1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8) → 3,4-Dimethylphenol (95-65-8) + acetophenone (98-86-2) + 3,4-dimethylacetophenone (3637-01-2) + phenol (108-95-2)

Conditions	Yield
Stage #1: 1,2-dimethyl-4-(1-phenylethyl)benzene With oxygen; N-hydroxyphthalimide; 2,2'-azobis(isobutyronitrile) In acetonitrile at 75℃; under 760.051 Torr; for 6h; Stage #2: With sulfuric acid In water; acetonitrile at 0℃; for 0.5h;	A 46% B 50% C 2.7% D n/a
Stage #1: 1,2-dimethyl-4-(1-phenylethyl)benzene With oxygen; N-hydroxyphthalimide; 2,2'-azobis(isobutyronitrile) In acetonitrile at 75℃; under 760.051 Torr; for 6h; Stage #2: In acetonitrile at 0℃; for 1h; Product distribution / selectivity;	A 50% B 50% C 1% D n/a

1,2-dimethyl-4-(1-phenylethyl)benzene (6196-95-8) → C16H18O2

Conditions	Yield
With N-hydroxyphthalimide; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; under 760.051 Torr;

Upstream product

• 100-42-5 styrene 
• 95-47-6 o-xylene 
• 7214-61-1 (1-nitroethyl)benzene 
• 93-92-5 1-phenylethyl acetate 
• 98-85-1 1-Phenylethanol 
• 14856-75-8 1-phenyl-1-trimethylsilyloxyethane 
• 112473-30-0 triethyl(1-phenylethoxy)silane 
• 92976-56-2 tert-butyldimethyl(1-phenylethoxy)silane 
• 93-96-9 bis(1-phenylethyl)ether 
• 2571-39-3 (3,4-dimethylphenyl)(phenyl)methanone 
• 38112-01-5 1-phenyl-1-(3,4-dimethylphenyl)ethylene 

Downstream Products

• 95-65-8 3,4-Dimethylphenol 
• 98-86-2 acetophenone 
• 3637-01-2 3,4-dimethylacetophenone 
• 108-95-2 phenol 

Relevant articles and documents

Green synthesis of 1-phenyl-1-ortho-xylene ethane in IL and reaction mechanism

1-Phenyl-1-ortho-xylene ethane (PXE) in IL was synthesized, and the catalysts used were AlCl3 in 1-butyl-3-methylimidazolium bromide ([BMIM][Br]) or 1-butyl-3-methylimidazolium chloride ([BMIM][Cl]), and H2SO4. When the concentrations of AlCl3 in IL, ortho-xylene and styrene were 0.35, 0.03 and 0.005?mol, respectively, it could be discovered that ([BMIM][Br]) was the best catalyst. When the mole fraction concentration of AlCl3/[BMIM][Br] was more than 0.40%, the reaction was able to achieve 100% conversion. When the reaction time was longer than 60 minutes, the percentage conversion of ortho-xylene attained was 100%. The mechanisms of the reaction were investigated by the DFT method at the B3LYP/6-311++G(d, p) level. The potential energy surface (PES) profile indicated that the energy of transition state was 22.59 kcal mol?1. This indicated that the activation energy of reaction was 28.24 kcal mol?1, which illustrated that the reaction occurred easily. Vibrational frequencies were observed in FT-IR spectra, the corresponding vibrational modes νs(H4-C3Al-H5) and νas(H4-C3Al-H5) indicated that an Al3+ ion was combined with a C3 atom. In addition, the repeated use of the catalysts was studied; the ionic liquids could still catalyze the reaction and the percentage yield of PXE was larger than 91% after 6 runs.

Alkylation of O-xylene and styrene catalyzed by cross-linked poly acidic ionic liquids catalyst with novel mesoporous-macroporous structure

Cross-linked poly acidic ionic liquids (MPM-C6V-SO3CF3-IL) with mesoporous and macroporous network structure have been synthesized in different solvents. The novel solid acid catalyst with special network structure has a large surface area (103.83 m2/g), large pore volume (0.72 cm3/g) and abundant mesopores and macropores, which help to improve the contact between active site and reactants. Catalytic performance of catalyst was investigated through alkylation of o-xylene and styrene. Different reaction parameters specifically solvent on obtained catalyst and production of PXE were systematically investigated. Under optimal reaction conditions (reaction time was 3 h, reaction temperature was 120 °C, catalyst amount was 0.17 g (0.5 wt%), and o-xylene/styrene mass ratio was 7.5:1), a high conversion of styrene (100%) and 1,2-diphenylethane (PXE) yield of 99.67% was obtained, which is superior to commercial acid in liquid and even previous acids synthesized by our own group. Moreover, catalyst could keep relatively high thermostability under reaction and are easy to be separated and recycled from the solution, which are critical for heterogeneous solid catalysts. Thus, this novel catalyst can be potentially applied in other acidic reactions.

Highly active and green aminopropyl-immobilized phosphotungstic acid on mesoporous LaSBA-15 for alkylation of o-xylene with styrene

The Keggin phosphotungstic acid, H3PW12O40 (HPW), was successfully immobilized on the surface of mesostructured LaSBA-15 by means of chemical bonding to aminosilane groups. The catalysts were characterized by elemental analysis, N2 adsoption, TEM, DRS-UV, and FTIR spectroscopy. Characterization results suggest that the surface area decreased after grafting amino groups to silica and the structures of heteropolyanions on amine-modified LaSBA-15 was maintained. Their catalytic behaviors were investigated in the alkylation of o-xylene with styrene. Among the functionalized catalysts, when the content of amino-groups was suitable, it had the best catalytic performances in terms of yield and stability. It is worth mentioning that the catalysts could be used repeatedly without loss of the activity and selectivity during several catalytic cycles. The good stability can be attributed to the strong interaction between the amino groups on the surface of LaSBA-15 and HPW anions.

One-step synthesis of hierarchical aluminosilicates using alkoxy-functionalized ionic liquid as a novel template

Hierarchical zeolites have bridged the gap between conventional zeolite and mesoporous materials, which not only maintain the excellent advantages of microporous sieves, but also effectively resolve the diffusion limitations. Herein, a novel alkoxy-functionalized ionic liquid was employed as a mesoporous structure-directing agent to synthesize hierarchical aluminosilicates with dual micro-mesoporous channels. X-ray diffraction (XRD), N2 adsorption-desorption isotherms (BET), scanning electron microscopy (SEM), transmission electron microscopy (TEM), temperature-programmed desorption (TPD), thermogravimetric analysis (TGA) and 27Al magic-angle spinning nuclear magnetic resonance (27Al MAS NMR) were used to characterize the structural and textural features of the hierarchical aluminosilicates. The results showed that the ionic liquid (MTPI) employed played the role of a mesoporous structure-directing agent which was trapped within the pores of a faujasite structure through -Si-O-Al- and -Si-O-Si- linkages. The mesoporous diameters and structures of the final hierarchical materials could be uniformly tailored by tuning the added amount of template. Hierarchical aluminosilicates with the combined advantages of both mesoporous properties and the microporous crystalline structure of zeolites exhibited high catalytic activity and resistance to deactivation in the alkylation of o-xylene with styrene, as compared to the conventional zeolite with the sole presence of micropores. The distinct catalytic performance of hierarchical aluminosilicates could be attributed to the short diffusion routes and abundant exposed acidic sites on the external surface.

Deep compositional understanding of TBA: AlCl3 ionic liquid for its applications

Chloroaluminate ionic liquids (ILs) have been immensely used as homogeneous catalyst in Friedel-Crafts reaction. We have recently synthesized chloroaluminate ILs by reacting aluminium chloride with a hydrophobic neutral ligand i.e. tributylamine (TBA:AlCl3). The current study elaborates on the investigations of the composition of the ionic liquids at various stages of their formation. The ionic liquids were synthesized using various mole ratios of tributyl amine and aluminium chloride in range of 1:1 to 1:2.3, in presence of an aromatic solvent in a one pot reaction. Various characterization techniques like Mass spectrometry, 27Al Nuclear Magnetic Resonance, 31P Nuclear Magnetic Resonance and Fourier Transform Infrared spectroscopy were used to elucidate the formation of various moieties of the TBA:AlCl3 Ionic Liquid. This study also elaborates on the investigations of the cationic and anionic moieties and their structure-property relationship for various applications. Various Friedel-Crafts reaction of industrial importance were performed using the ionic liquid having (Al2Cl7)?moiety to assess its performance and compared with conventional processes. The synthesized products were characterised by sophisticated analytical techniques like 1H NMR, 13C NMR, FTIR, GC–MS, GC-FID, to name a few. This class of ionic liquids also have importance in various electrochemical applications like aluminium deposition and aluminium batteries.