106-42-3

Basic information

• Product Name: 1,4-Dimethylbenzene
• Synonyms: p-Xylene(8CI);1,4-Xylene;4-Methyltoluene;NSC 72419;p-Dimethylbenzene;p-Methyltoluene;p-Phenylenebis(methylene);p-Xylol;1,4-Dimethylbenzene
• CAS NO: 106-42-3
• Molecular Formula: C₈H₁₀
• Molecular Weight: 106.1674
• EINECS: 203-396-5
• Product Categories: Industrial/Fine Chemicals;Analytical Chemistry;Standard Solution of Volatile Organic Compounds for Water & Soil Analysis;Standard Solutions (VOC);Amber Glass Bottles;Analytical Reagents;Analytical/Chromatography;CHROMASOLV for HPLC;Chromatography Reagents &;HPLC &;HPLC Grade Solvents (CHROMASOLV);HPLC/UHPLC Solvents (CHROMASOLV);Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;UHPLC Solvents (CHROMASOLV)
• Mol File: 106-42-3.mol

Chemical Properties

• Melting Point: 13-13℃
• Boiling Point: 139.61 °C at 760 mmHg
• Flash Point: 27.22 °C
• Appearance: colourless liquid
• Density: 0.87 g/cm³
• Vapor Density: 3.7 (vs air)
• Vapor Pressure: 7.943mmHg at 25°C
• Refractive Index: n20/D 1.495(lit.)
• Storage Temp.: 0-6°C
• Solubility: water: soluble0.2g/L
• PKA: >15 (Christensen et al., 1975)
• Water Solubility: Miscible with alcohol, ether, acetone, benzene and chloroform. Immiscible with water.
• Stability: Stable. Incompatible with oxidizing agents. Hygroscopic. Flammable.
• Merck: 14,10081
• BRN: 1901563
• CAS DataBase Reference: 1,4-Dimethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dimethylbenzene(106-42-3)
• EPA Substance Registry System: 1,4-Dimethylbenzene(106-42-3)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R10:Flammable.; R20/21:Harmful by inhalation and in contact with skin.; R38:Irritating to skin.
• Safety Statements: S25:Avoid contact with eyes.
• RIDADR: UN 1307 3/PG 3
• WGK Germany: 2
• RTECS: ZE2625000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 106-42-3(Hazardous Substances Data)

Usage

Uses

1. Used in the Chemical Industry:
1,4-Dimethylbenzene is used as a precursor for the production of various chemicals, including benzoic acid, isophthalic acid, and terephthalic acid, which are used in the manufacture of polyester fibers and other plastic and rubber products.
2. Used as a Solvent:
1,4-Dimethylbenzene is used as a solvent in the paint, coatings, and rubber industries due to its ability to dissolve a wide range of substances.
3. Used in the Production of Dyes and Drugs:
p-Xylene is used as a raw material for the production of dyes, drugs, pesticides, and many organic intermediates, such as terephthalic acid and phthalic anhydride.
4. Used in Microscopy:
1,4-Dimethylbenzene is used with Canada balsam as an oil-immersion medium in microscopy and as a clearing agent in microscope techniques.
Physical Properties:
1,4-Dimethylbenzene is a clear, colorless, watery liquid with a sweet odor. It has an odor threshold concentration of 47 ppbv in air. It is less dense than water and has a freezing point of 56°F. The flash point of p-xylene is 27°C, making it dangerously flammable.

References

1.https://en.wikipedia.org/wiki/P-Xylene 2.https://pubchem.ncbi.nlm.nih.gov/compound/p-xylene#section=Top 3.https://www.chemicalsafetyfacts.org/paraxylene/

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 3247, 1988 DOI: 10.1021/jo00249a020Tetrahedron Letters, 26, p. 1935, 1985 DOI: 10.1016/S0040-4039(00)98345-X

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

P-XYLENE may react with oxidizing materials. . Acetic acid forms explosive mixtures with P-XYLENE and air (Shraer, B.I. 1970. Khim. Prom. 46(10):747-750.).

Health Hazard

Vapors cause headache and dizziness. Liquid irritates eyes and skin. If taken into lungs, causes severe coughing, distress, and rapidly developing pulmonary edema. If ingested, causes nausea, vomiting, cramps, headache, and coma. Can be fatal. Kidney and liver damage can occur.

Health Hazard

The toxic properties of xylene isomers aresimilar to toluene or ethylbenzene. The targetorgans are the central nervous system, eyes,gastrointestinal tract, kidneys, liver, blood,and skin, which, however, are affected onlyat high levels of exposure. In humans itsexposure may cause irritation of the eyes,nose, and throat, headache, dizziness, excitement,drowsiness, nausea, vomiting, abdominalpain, and dermatitis. The irritation effectsin humans may be felt at a concentration of200 ppm in air, while exposure to 10,000 ppmfor 6–8 hours may be fatal.The oral toxicity of xylene is low. Ingestionof a high dose, however, can causedepression of the central nervous system,dizziness, nausea, and vomiting and abdominalpain. The oral LD50 values in ratsfor xylene isomers are within the range of5000 mg/kg.The major route of absorption of xyleneis inhalation. Another significant route isskin absorption of the liquid. About 5% ofabsorbed xylene is excreted unchanged inexpired air within a few hours, while less than2% is hydroxylated to xylenols. Over 90% ofabsorbed xylenes are metabolized to o-, m-,and p-isomers of methyl benzoic acid andexcreted in urine as methyl hippuric acids(ACGIH 1986). Small amounts of xylenesmay remain stored in adipose tissue. Repeatedexposures may cause accumulation in theblood.

Fire Hazard

Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back.

Flammability and Explosibility

Flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion and inhalation. An experimental teratogen. Experimental reproductive effects. May be narcotic in hgh concentrations. Chronic toxicity not established, but is less toxic than benzene. A very dangerous fire hazard when exposed to heat or flame; can react with oxidzing materials. Explosive in the form of vapor when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. Potentially explosive reaction with acetic acid + air, 1,3-dichloro-5,5-dimethyl-2,4- imidazolidinhone, nitric acid + pressure. When heated to decomposition it emits acrid smoke and irritating fumes. See also other xylene entries.

Source

Detected in distilled water-soluble fractions No. 2 fuel oil (1.11 mg/L), jet fuel A (1.23 mg/L), diesel fuel (0.56 mg/L), and military jet fuel JP-4 (5.48 mg/L) (Potter, 1996); in new and used motor oil at concentrations of 0.26 to 0.29 and 302 to 339 μg/L, respectively (Chen et al., 1994). The average volume percent and estimated mole fraction in American Petroleum Institute PS-6 gasoline are 1.809 and 0.02263, respectively (Poulsen et al., 1992). Diesel fuel obtained from a service station in Schlieren, Switzerland contained m/p-xylene at a concentration of 336 mg/L (Schluep et al., 2001). Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 602. Average m+p-xylene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 8.611, 0.658, and 0.228 mg/L, respectively. When the authors analyzed the aqueous-phase via U.S. EPA approved test method 610, average m+p-xylene concentrations in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were lower, i.e., 6.068, 0.360, and 0.222 mg/L, respectively. Based on laboratory analysis of 7 coal tar samples, m+p-xylene concentrations ranged from ND to 6,000 ppm (EPRI, 1990). Detected in 1-yr aged coal tar film and bulk coal tar at concentrations of 260 and 830 mg/kg, respectively (Nelson et al., 1996). A high-temperature coal tar contained pxylene at an average concentration of 0.03 wt % (McNeil, 1983). Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of m-xylene + p-xylene was 60.0 mg/kg of pine burned. Emission rates of both isomers were not measured during the combustion of oak and eucalyptus. Drinking water standard (final): For all xylenes, the MCLG and MCL are both 10 mg/L. In addition, a DWEL of 70 mg/L was recommended (U.S. EPA, 2000).

Environmental fate

Biological. Microbial degradation of p-xylene produced 4-methylbenzyl alcohol, pmethylbenzaldehyde, p-toluic acid, and 4-methylcatechol (quoted, Verschueren, 1983). Dimethylcis, cis-muconic acid, and 2,3-dihydroxy-p-toluic acid were reported to be biooxidation products of p-xylene by Nocardia corallina V-49 using n-hexadecane as the substrate (Keck et al., 1989). Reported biodegradation products of the commercial product containing xylene include α-hydroxy-p-toluic acid, p-methylbenzyl alcohol, benzyl alcohol, 4-methylcatechol, m- and ptoluic acids (Fishbein, 1985). It was reported that p-xylene was cometabolized resulting in the formation of p-toluic and 2,3-dihydroxy-o-toluic acids (Pitter and Chudoba, 1990). In anoxic groundwater near Bemidji, MI, p-xylene anaerobically biodegraded to the intermediate p-toluic acid (Cozzarelli et al., 1990). In gasoline-contaminated groundwater, methylbenzylsuccinic acid was identified as the first intermediate during the anaerobic degradation of xylenes (Reusser and Field, 2002). Photolytic. A n-hexane solution containing m-xylene and spread as a thin film (4 mm) on cold water (10 °C) was irradiated by a mercury medium pressure lamp. In 3 h, 18.5% of the p-xylene photooxidized into p-methylbenzaldehyde, p-benzyl alcohol, p-benzoic acid, and pmethylacetophenone (Moza and Feicht, 1989). Glyoxal and methylglyoxal were produced from the photooxidation of p-xylene by OH radicals in air at 25 °C (Tuazon et al., 1986a). The rate constant for the reaction of p-xylene and OH radicals at room temperature was 1.22 x 10-11 cm3/molecule?sec (Hansen et al., 1975). A rate constant of 7.45 x 10-9 L/molecule?sec was reported for the reaction of p-xylene with OH radicals in the gas phase (Darnall et al., 1976). Similarly, a room temperature rate constant of 1.41 x 10-11 cm3/molecule?sec was reported for the vapor-phase reaction of p-xylene with OH radicals (Atkinson, 1985). At 25 °C, a rate constant of 1.29 x 10-11 cm3/molecule?sec was reported for the same reaction (Ohta and Ohyama, 1985). Chemical/Physical. Under atmospheric conditions, the gas-phase reaction with OH radicals and nitrogen oxides resulted in the formation of p-tolualdehyde (Atkinson, 1990). Kanno et al. (1982) studied the aqueous reaction of p-xylene and other aromatic hydrocarbons (benzene, toluene, oand m-xylene, and naphthalene) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. The amount of cyanogen chloride formed increased at lower pHs (Kanno et al., 1982). Products identified from the OH radical-initiated reaction of p-xylene in the presence of nitrogen dioxide were 3-hexene-2,5-dione, p-tolualdehyde, and 2,5-dimethylphenol (Bethel et al., 2000).

Purification Methods

The general purification methods listed for xylene above are applicable. p-Xylene can readily be separated from its isomers by crystallisation from such solvents as MeOH, EtOH, isopropanol, acetone, butanone, toluene, pentane or pentene. It can be further purified by fractional crystallisation by partial freezing, and stored over sodium wire or molecular sieves Linde type 4A. [Stokes & French J Chem Soc, Faraday Trans 1 76 537 1980, Beilstein 5 H 382, 5 I 185, 5 II 296, 5 III 845, 5 IV 951.]

InChI:InChI:1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3

Synthetic route

4-methyl-benzaldehyde (104-87-0) → para-xylene (106-42-3)

Conditions	Yield
With hydrogen In water; ethyl acetate at 50℃; under 15001.5 Torr; for 5h;	99%
With hydrogen In water at 25℃; for 1h;	99%
With hydrogen at 350℃; under 760.051 Torr;	95%

ethene (74-85-1) + 2,5-hexanedione (110-13-4) → para-xylene (106-42-3)

Conditions	Yield
With solid acid catalyst tin phosphate In n-heptane at 300℃; under 15001.5 Torr; for 12h; Reagent/catalyst; Solvent; Pressure; Temperature;	90%
With copper(II) bis(trifluoromethanesulfonate) at 250 - 270℃; under 26892.4 - 82745.9 Torr; for 5h; Inert atmosphere;	44%

2,5-dimethylfuran (625-86-5) + ethene (74-85-1) → para-xylene (106-42-3)

Conditions	Yield
With P-containing zeolite Beta In n-heptane at 250℃; under 46504.7 Torr; Reagent/catalyst; Diels-Alder Cycloaddition;	97%
With benzoic acid anhydride In acetic acid at 280℃; under 63006.3 Torr; for 8h; Pressure; Reagent/catalyst; Solvent; Temperature; Time;	92.3%
With copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 270℃; under 26892.4 - 82745.9 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;	91%

2,5-dimethylfuran (625-86-5) + ethene (74-85-1) → para-xylene (106-42-3) + 2,5-hexanedione (110-13-4)

Conditions	Yield
In n-heptane at 249.84℃; under 37503.8 Torr; for 24h; Reagent/catalyst; Autoclave; Inert atmosphere;	A 75% B n/a
In acetic acid at 280℃; under 63006.3 Torr; for 4h; Pressure; Reagent/catalyst; Solvent; Temperature; Time;	A 68.5% B 12.1%
With Sn-BEA In n-heptane at 250℃; under 46504.7 Torr; for 24h; Catalytic behavior; Kinetics; Diels-Alder Cycloaddition; Autoclave; Inert atmosphere; chemoselective reaction;	A 43% B n/a

methanol (67-56-1) + toluene (108-88-3) → o-xylene (95-47-6) + para-xylene (106-42-3) + m-xylene (108-38-3)

Conditions	Yield
With hydrogen; P-modified ZSM-5 In water at 480 - 485℃; under 1794.37 Torr; for 23.53h; Product distribution / selectivity;	A n/a B 15.54% C n/a
H-ZSM-5(73) at 400℃; Product distribution; further catalysts (alumosilicates, modified zeolites);
Na(+)x(Mg3)(Si(4-x)Alx)O10(OH)2 at 349.9℃; for 1h; Product distribution; various pillared clays and zeolites as catalysts;

methanol (67-56-1) + toluene (108-88-3) → para-xylene (106-42-3)

Conditions	Yield
With hydrogen In water at 400℃; under 3750.38 Torr; Reagent/catalyst; Pressure; Temperature; Concentration; Inert atmosphere;	29.3%
With hydrogen at 250℃; Kinetics; Thermodynamic data; Further Variations:; pH-values;
silica bound HZSM-5 zeolite at 600℃; under 3620.13 - 4137.29 Torr; for 3.25 - 7.5h; Conversion of starting material;

4-Methylbenzyl alcohol (589-18-4) + benzamide (55-21-0) → para-xylene (106-42-3) + N-(p-methylbenzyl)benzamide (65608-94-8)

Conditions	Yield
With barium trifluoromethanesulfonate In toluene at 150℃; for 18h; Reagent/catalyst; Glovebox; Inert atmosphere;	A 29% B 72%

o-xylene (95-47-6) + m-xylene (108-38-3) → para-xylene (106-42-3)

Conditions	Yield
With hydrogen; silicate ITQ-13, aluminium form at 360℃; under 10343.2 Torr; Product distribution / selectivity; fixed-bed downflow reactor;	23.5%
MTW-zeolite/Al2O3 (Catalyst B) at 280℃; under 26618.1 Torr; Conversion of starting material; Liquid phase;
Ga-MFI zeolite/ZrO2/Al2O3 (Catalyst C) at 300℃; under 26618.1 Torr; Conversion of starting material; Liquid phase;

2,5-dimethylfuran (625-86-5) + ethene (74-85-1) → para-xylene (106-42-3) + 3,6-dimethylcyclohex-2-enone (15329-10-9) + 2,5-hexanedione (110-13-4)

Conditions	Yield
With H-BEA-25 In 1,4-dioxane at 249.84℃; under 15001.5 Torr; for 4h; Diels-Alder Cycloaddition; Autoclave; chemoselective reaction;

1,4-dimethylcyclohex-1-ene (2808-79-9) → para-xylene (106-42-3)

Conditions	Yield
With palladium on activated charcoal In toluene at 130℃; under 7500.75 - 30003 Torr; for 3h; Autoclave;

1,4-dimethyl-7-oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid anhydride (111957-97-2) → 3,6-dimethyl phthalic anhydride (5463-50-3) + para-xylene (106-42-3)

Conditions	Yield
With zeolite Y with a silica-alumina at 200℃; for 2h; Temperature; Inert atmosphere;	A 72% B 17%
With 1 wtpercent Pd/C loaded on zeolite H-Y with a silica-alumina ratio of 40 In toluene at 200℃; under 750.075 Torr; for 4h; Inert atmosphere;

4-Methylbenzyl alcohol (589-18-4) + benzamide (55-21-0) → para-xylene (106-42-3) + N-(p-methylbenzyl)benzamide (65608-94-8) + N,N′‑(4‑methylbenzylidene)bisbenzamide (40891-10-9)

Conditions	Yield
With indium sulfate In toluene at 150℃; for 18h; Glovebox; Inert atmosphere;	A 60% B 14% C 40%
With zinc(II) sulfate In toluene at 150℃; for 18h; Glovebox; Inert atmosphere;	A 41% B 58% C 6%
With zinc(II) chloride In toluene at 150℃; for 18h; Glovebox; Inert atmosphere;	A 47% B 42% C 21%

ethylbenzene (100-41-4) → para-xylene (106-42-3)

Conditions	Yield
With hydrogen at 480℃; under 8826.09 Torr; Leiten ueber Platin/Aluminiumoxid-Siliciumdioxid;
With hydrogen; 0.3 wtpercent Pt/0.1 wtpercent S/100 wtpercent MTW-zeolite (Catatalyst C) at 370 - 375℃; under 4650.47 Torr; Conversion of starting material;
With hydrogen; 0.3 wtpercent Pt/0.1 wtpercent S/50 wtpercent MTW/50 wtpercent mordenite (Catalyst F) at 370 - 375℃; under 4650.47 Torr; Conversion of starting material;

methanol (67-56-1) + toluene (108-88-3) + benzene (71-43-2) → o-xylene (95-47-6) + para-xylene (106-42-3) + m-xylene (108-38-3)

Conditions	Yield
With hydrogen; 1/16 inch extrudates which contained 65 weight percent H-ZSM-5 and 35 weight percent silica binder at 371.101℃; under 3309.83 Torr;
With hydrogen; 1/16 inch extrudates which contained 65 wt. percent H-ZSM-23 having a silica to alumina mole ratio of 110:1 and 35 wt. percent of alumina binder at 499.99℃; under 7757.43 Torr;
With hydrogen; SAPO-11 at 499.99℃; under 7757.43 Torr;

methanol (67-56-1) + toluene (108-88-3) + benzene (71-43-2) → para-xylene (106-42-3)

Conditions	Yield
With hydrogen; silica selectivated ZSM-5 at 371.101℃; under 10343.2 Torr;

4-methyl-benzaldehyde (104-87-0) → 4-Methylbenzyl alcohol (589-18-4) + para-xylene (106-42-3)

Conditions	Yield
With triethylsilane; palladium dichloride In ethanol for 0.5h; Inert atmosphere;	A 10.0 %Chromat. B 88.5 %Chromat.
With palladium on silica; hydrogen In dodecane at 190℃; under 22502.3 Torr; for 5h;
With palladium on activated charcoal; hydrogen In water at 100℃; for 10h; chemoselective reaction;	A 40 %Chromat. B 60 %Chromat.

m-xylene (108-38-3) → o-xylene (95-47-6) + para-xylene (106-42-3)

Conditions	Yield
With parent microporous ZSM-5 zeolite at 250℃; for 0.25h; Reagent/catalyst;	A 27% B 10%
With hydrogen; H-ZSM-5 at 349.9℃; under 15001.2 Torr; Product distribution; further catalysts, variation of temperature;
CVD boria-alumina at 450℃; Product distribution; dependence of conversion on B2O3 content of catalyst;

para-chlorotoluene (106-43-4) + bis{μ-[2-(dimethylamino)ethanolato-N,O:O]}tetramethyldialuminum → para-xylene (106-42-3)

Conditions	Yield
With tri-tert-butyl phosphine; {MoPdcp[μ-(CO)2][μ3-(CO)](PPh3)}2 In benzene at 120℃; for 15h;	98%

toluene (108-88-3) → para-xylene (106-42-3) + benzene (71-43-2)

Conditions	Yield
With hydrogen; platinum-containing ZSM-5 molecular sieve catalyst at 420℃; under 11251.1 Torr;
With hydrogen; alumina-phosphate-bound MFI catalyst at 560℃; under 18376.8 Torr; Gas phase;
With hydrogen; alumina-phosphate-bound MFI catalyst at 560℃; under 18376.8 Torr; Gas phase;

4-Methylbenzyl alcohol (589-18-4) + benzamide (55-21-0) → para-xylene (106-42-3) + N-(p-methylbenzyl)benzamide (65608-94-8) + bis(4-methylbenzyl) ether (38460-98-9)

Conditions	Yield
With tin(II) trifluoromethanesulfonate In toluene at 150℃; for 18h; Glovebox; Inert atmosphere;	A 8% B 33% C 50%
With zinc trifluoromethanesulfonate In toluene at 150℃; for 18h; Reagent/catalyst; Glovebox; Inert atmosphere;	A 33% B 22% C 21%

2,5-dimethylfuran (625-86-5) + ethene (74-85-1) → para-xylene (106-42-3) + p-n-propyltoluene (1074-55-1) + 2-ethyl-p-xylene (1758-88-9)

Conditions	Yield
With palladium-decorated gold nanoparticles anchored on amphoteric zirconia In n-heptane at 300℃; under 30402 Torr; for 6h;

2,5-dimethylfuran (625-86-5) + ethene (74-85-1) → 4,4-dimethylcyclohexenone (1073-13-8) + para-xylene (106-42-3) + 3,6-dimethylcyclohex-2-enone (15329-10-9)

Conditions	Yield
With Sn-BEA In n-heptane at 275℃; under 30402 Torr; for 1h;

triplal (854432-99-8) → para-xylene (106-42-3) + 1,2,4-Trimethylbenzene (95-63-6)

Conditions	Yield
With palladium/alumina; hydrogen In hexane at 325℃; Flow reactor; Green chemistry;	A 84.8% B 6.5%
With hydrogen In hexane at 325℃; Flow reactor; Green chemistry;	A 19.5% B 73.2%

4-Methylbenzyl chloride (104-82-5) → para-xylene (106-42-3) + 1,2-di-p-tolylethane (538-39-6)

Conditions	Yield
With copper nickel; pyrographite In 1,2-dimethoxyethane at 85℃; for 20h;	A 10% B 90%
With nickel In 1,2-dimethoxyethane for 2h; Ambient temperature;	A 20% B 76%
With magnesium at 600℃;	A 23% B 60%
With water; naphthalen-1-yl-lithium In tetrahydrofuran; diethyl ether; Petroleum ether at -95℃; for 0.75h; Title compound not separated from byproducts;	A 64 % Chromat. B 36 % Chromat.

methanol (67-56-1) + toluene (108-88-3) → para-xylene (106-42-3) + m-xylene (108-38-3)

Conditions	Yield
With Ga2O3 zeolite; silica gel In gas at 400℃; Product distribution; var. catalyst, var. temp.;
With hydrogen; Catalyst G (prepared from NH4-ZSM-5 and H3PO4) at 200 - 500℃; under 1034.32 Torr; Product distribution / selectivity;
With hydrogen; Catalyst H (prepared from NH4-ZSM-5 and H3PO4) at 200 - 500℃; under 1034.32 Torr; Product distribution / selectivity;

carbon monoxide (201230-82-2) + p-xylylene glycol (589-29-7) → para-xylene (106-42-3) + 1,4-phenylenediacetic acid (7325-46-4) + 4-tolylacetic acid (622-47-9)

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A n/a B 48% C 16%

methanol (67-56-1) + toluene (108-88-3) + benzene (71-43-2) → o-xylene (95-47-6) + para-xylene (106-42-3) + ethylbenzene (100-41-4) + m-xylene (108-38-3)

Conditions	Yield
With hydrogen; silicon-selectivated H-ZSM-5/silica bound at 371.101℃; under 10343.2 Torr;
With hydrogen; zeolite bound zeolite at 371.101℃; under 10343.2 Torr;

o-xylene (95-47-6) + ethylbenzene (100-41-4) + m-xylene (108-38-3) → para-xylene (106-42-3)

Conditions	Yield
catalyst contained 15.0percentw EU-1 zeolite in H form, 84.7percentw Al2O3, 0.3percentw Pt and treated with dimethyldisulphide at 390℃; under 11251.1 Torr; Product distribution / selectivity;
catalyst contained 15.0percentw NU-87 zeolite in H form, 84.7percentw Al2O3, 0.3percentw Pt and treated with dimethyldisulphide at 390℃; under 11251.1 Torr; Product distribution / selectivity;
catalyst contained 8.0percentw EU-1 zeolite in H form, 7.0percentw NU-87 zeolite in H form, 84.7percentw Al2O3, 0.15percentw Pt, 0.15percentw Re and treated with dimethyldisulphide at 390℃; under 11251.1 Torr; Product distribution / selectivity;

4-Methylbenzyl alcohol (589-18-4) → para-xylene (106-42-3)

Conditions	Yield
With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction;	99%
Multi-step reaction with 2 steps 1: hydrogen; / 350 °C / 760.05 Torr 2: hydrogen; / 350 °C / 760.05 Torr View Scheme
With formic acid; methanesulfonic acid; 1,2-bis((di-tert-butylphosphoryl)methyl)benzene; palladium(II) acetylacetonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	93 %Chromat.
With 2,4,6-trimethyl-pyridine; 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation;	63 %Chromat.

carbon monoxide (201230-82-2) + toluene (108-88-3) → o-xylene (95-47-6) + para-xylene (106-42-3) + m-xylene (108-38-3)

Conditions	Yield
With hydrogen at 400℃; under 24549.5 Torr; Temperature; Flow reactor; Inert atmosphere;

para-xylene (106-42-3) → 4-bromo-m-xylene (553-94-6)

Conditions	Yield
With potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 0.16h; Product distribution; under argon;	100%
With oxygen; potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 5h; Product distribution;	96%
With sulfuric acid; dihydrogen peroxide; sodium bromide In water at 49.84℃;	94%

para-xylene (106-42-3) → mononitro-p-xylene (89-58-7)

Conditions	Yield
With zeolite ZSM-5-60; Nitrogen dioxide	100%
With nitric acid; sulfuric acid In dichloromethane at 25℃; for 0.7h;	100%
With nitric acid In toluene at 60℃; for 2h;	98%

para-xylene (106-42-3) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With oxygen; 10-methyl-9-phenylacridin-10-ium perchlorate In chloroform at 24.84℃; for 10h; Oxidation; Pyrolysis; visible light;	100%
With sulfuric acid; 9-mesityl-2,7,10-trimethylacridinium perchlorate; water; oxygen In acetonitrile at 24.84℃; for 1.33333h; Quantum yield; Reagent/catalyst; Irradiation;	100%
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate; acetic acid at 20℃; under 760.051 Torr; chemoselective reaction;	100%

para-xylene (106-42-3) → 4-Methylbenzyl bromide (104-81-4)

Conditions	Yield
With bromine In tetrachloromethane Solvent;	100%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; silica gel for 4.5h; UV-irradiation;	84%
With bromine In tetrachloromethane for 1.5h; Ambient temperature;	83%

para-xylene (106-42-3) → 1,4 dimethylcyclohexane (589-90-2)

Conditions	Yield
With hydrogen; [(norbornadiene)rhodium(I)chloride]2; phosphinated polydiacetylene In n-heptane at 30℃; under 60800 Torr; for 1.5h;	100%
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 120℃; under 37503.8 Torr; for 18h;	100%
With hydrogen at 150℃; under 2280.15 Torr; for 0.5h; Kinetics; Reagent/catalyst; Temperature;	100%

para-xylene (106-42-3) + benzoyl chloride (98-88-4) → 2,5-dimethylbenzophenone (4044-60-4)

Conditions	Yield
With tris(fluorosulphonyl)methane at 138℃; for 3h;	100%
Hf[N(SO2C8F17)2]4 In various solvent(s) at 120℃; for 3h;	98%
With C4F9SO3H at 138℃; for 5h;	91%

[Cp*Ru(CH3CN)3]OTf (113860-02-9) + para-xylene (106-42-3) → {C5(CH3)5}Ru{C6H4(CH3)2}(1+)*CF3SO3(1-)={(C5(CH3)5)Ru(C6H4(CH3)2)}(CF3SO3)

Conditions	Yield
In tetrahydrofuran byproducts: CH3CN; under N2; addn. of Ru-complex to p-xylene and THF (benzene-free), mixt. stirred (30°C); addn. of hexane, solid filtered, washed twice (hexane), dried (vac.), elem. anal.;	100%

para-xylene (106-42-3) + 3-nitro-benzaldehyde (99-61-6) + allyl-trimethyl-silane (762-72-1) → tetrahydro-4-(2,5-dimethylphenyl)-2,6-bis(3-nitrophenyl)-2H-pyran (1157865-90-1)

Conditions	Yield
With boron trifluoride diethyl etherate at 0 - 20℃; for 2h; Sakurai-Hosomi-Prins-Friedel-Crafts reaction; stereoselective reaction;	100%

para-xylene (106-42-3) + C6H6*C33H30N12S3 (1280197-89-8) → 0.25C8H10*C33H30N12S3

Conditions	Yield
at 40℃; for 480h; Gas phase;	100%

4-tert-Butylbenzyl alcohol (877-65-6) + para-xylene (106-42-3) → 2-(4-(tert-butyl)benzyl)-1,4-dimethylbenzene

Conditions	Yield
With (diethylamino)difluorosulfonium tetrafluoroborate In dichloromethane at 20℃; for 4h; Inert atmosphere;	100%

para-xylene (106-42-3) + (6-bromo-2-methylimidazo[1,2-a]pyridin-3-yl)methanol → 6-bromo-3-[(2,5-dimethylphenyl)methyl]-2-methylimidazo[1,2-a]pyridine

Conditions	Yield
With methanesulfonic acid at 100℃; for 1h;	100%

para-xylene (106-42-3) + 2-bromo-5-chlorobenzyl bromide (66192-24-3) → 2-(2-bromo-5-chlorobenzyl)-1,4-dimethylbenzene

Conditions	Yield
With indium(III) bromide In dichloromethane for 6h; Schlenk technique; Inert atmosphere; Molecular sieve;	100%

para-xylene (106-42-3) → terephthalic acid (100-21-0)

Conditions	Yield
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid at 200℃; under 30753.1 Torr; for 10h; Time; Temperature; Reagent/catalyst; Concentration; Inert atmosphere;	99.9%
With oxovanadium(IV) sulfate; hydrogen bromide; oxygen; acetic acid In water at 100℃; under 750.075 Torr; for 20h;	98%
With oxygen; acetic acid; hydrogen bromide; cobalt(II) acetate; manganese(II) acetate In water at 200℃; under 22502.3 Torr; for 0.05h; Product distribution / selectivity; Inert atmosphere;	98.3%

para-xylene (106-42-3) → p-Xylylene dichloride (623-25-6)

Conditions	Yield
With chlorine; 3-butyl-1,2-dimethylimidazolium chloride In perfluoroheptane at 84℃; for 3h; Temperature; Solvent;	99.11%
With chlorine; 3-butyl-1,2-dimethylimidazolium chloride at 120℃; for 3h; Reagent/catalyst; Temperature; Ionic liquid; Irradiation;	99.1%
durch Chlorieren;

para-xylene (106-42-3) → p-benzylchloride

Conditions	Yield
Stage #1: para-xylene With 1-dodecyl-3-methylimidazol-1-ium chloride at 110℃; Irradiation; Stage #2: With chlorine at 90 - 120℃; Reagent/catalyst; Temperature; Reflux;	99.11%

1,1-Diphenylmethanol (91-01-0) + para-xylene (106-42-3) → ((2,5-dimethylphenyl)methylene)dibenzene (7249-83-4)

Conditions	Yield
With silica gel supported sodium hydrogen sulfate at 80℃; for 0.5h; Friedel-Crafts type alkylation;	99%
With H5CoW12O40 supported on rice husk ash extracted nano silica at 60℃; for 0.666667h; Reagent/catalyst; Green chemistry;	98%
With Fe3O4/FeO at 60℃; for 0.333333h; Green chemistry;	92%

para-xylene (106-42-3) → p-Toluic acid (99-94-5)

Conditions	Yield
With tert.-butylhydroperoxide; water at 20℃; for 10h; Inert atmosphere;	99%
With N-hydroxy-tetrahydrophthalimide; oxygen; nitric acid at 50℃; under 750.075 - 1500.15 Torr; for 25h; Autoclave; Green chemistry;	91.16%
With MoO(O2)(8-quinolinolate)2; dihydrogen peroxide In acetonitrile for 6h; Oxidation; Heating;	88%

para-xylene (106-42-3) + acetyl chloride (75-36-5) → 1-(2,5-dimethylphenyl)-1-ethanone (2142-73-6)

Conditions	Yield
With aluminum (III) chloride In chloroform at 0 - 20℃; Inert atmosphere;	99%
With aluminum (III) chloride In carbon disulfide at 0 - 20℃; Friedel Crafts acylation; Inert atmosphere;	95%
Friedel-Crafts alkylation;	90%

para-xylene (106-42-3) + benzoic acid anhydride (93-97-0) → 2,5-dimethylbenzophenone (4044-60-4)

Conditions	Yield
sulfated zirconia at 100℃; for 2h; Product distribution; Further Variations:; Catalysts; Friedel-Crafts acylation;	99%
With C4F9SO3H at 138℃; for 5h;	93%

para-xylene (106-42-3) + 1-bromomethyl-4-bromobenzene (589-15-1) → 1,4-dimethyl-2-(4-bromobenzyl)benzene

Conditions	Yield
With indium(III) chloride; 4 A molecular sieve In dichloromethane at 20℃; for 16h; Friedel-Crafts alkylation;	99%
With potassium cyanide; aluminum oxide at 50℃; for 5h;	83 % Chromat.

Upstream product

• 15045-43-9 2,2,5,5-tetramethyltetrahydrofuran 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 56428-04-7 (4-tert-butyl-benzyl)-(4-methyl-benzyl)-ether 
• 920-39-8 isopropylmagnesium bromide 
• 2947-61-7 (4-methylphenyl)acetonitrile 
• 540-84-1 2,2,4-trimethylpentane 
• 592-13-2 2,5-dimethylhexane 
• 14435-92-8 carbonyl azide 
• 589-81-1 3-methylheptane 
• 927-98-0 2,5-dimethyl-hexa-1,3t-diene 
• 95-47-6 o-xylene 
• 622-75-3 1,4-phenylenediacetonitrile 

Downstream Products

• 4238-10-2 2,5,2',5'-tetramethyl-bibenzyl 
• 6972-51-6 2-(2,5-dimethylphenyl)ethan-1-ol 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 622-96-8 4-methylethylbenzene 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 56290-55-2 1-(2,5-dimethyl-phenyl)-butane-1,3-dione 
• 1453-06-1 4-(p-xylyl)butyric acid 
• 20116-65-8 dimethyl 4-methylphthalate 
• 37902-49-1 dimethyl 3,6-dimethylphthalate 
• 4338-65-2 3-(4-methylbenzyl)dihydrofuran-2,5-dione 
• 15254-22-5 (E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid 
• 6165-51-1 1,4-dimethyl-2-(1-phenylethyl)benzene 
• 28591-11-9 4-(2,5-Dimethylphenyl)valeriansaeure 

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Structural analysis of liquid 1,4-Dimethylbenzene (cas 106-42-3) at 293 K08/19/2019

Structural analysis of liquid 1,4-dimethylbenzene C6H4(CH3)2 by X-ray monochromatic radiation scattering method was performed. The X-ray measurements were made at room temperature for the scattering angle range Θ varying from 3 to 60°. The most probable parameters of 1,4-dimethylbenzene molecu...detailed

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