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106-42-3

Basic Information
CAS No.: 106-42-3
Name: 1,4-Dimethylbenzene
Article Data: 698
Cas Database
Molecular Structure:
Molecular Structure of 106-42-3 (1,4-Dimethylbenzene)
Formula: C8H10
Molecular Weight: 106.167
Synonyms: p-Xylene(8CI);1,4-Xylene;4-Methyltoluene;NSC 72419;p-Dimethylbenzene;p-Methyltoluene;p-Phenylenebis(methylene);p-Xylol;1,4-Dimethylbenzene;
EINECS: 203-396-5
Density: 0.87 g/cm3
Melting Point: 12-13 °C(lit.)
Boiling Point: 139.61 °C at 760 mmHg
Flash Point: 27.22 °C
Solubility: miscible with ethanol, ether, benzene and acetone, insoluble in water
Appearance: colourless liquid
Hazard Symbols: HarmfulXn,ToxicT
Risk Codes: 10-20/21-38-39/23/24/25-23/24/25
Safety: 25-45-36/37
Transport Information: UN 1307 3/PG 3
PSA: 0.00000
LogP: 2.30340
Synthetic route
104-87-0

4-methyl-benzaldehyde

106-42-3

para-xylene

Conditions
ConditionsYield
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%
74-85-1

ethene

110-13-4

2,5-hexanedione

106-42-3

para-xylene

Conditions
ConditionsYield
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%
625-86-5

2,5-dimethylfuran

74-85-1

ethene

106-42-3

para-xylene

Conditions
ConditionsYield
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%
625-86-5

2,5-dimethylfuran

74-85-1

ethene

A

106-42-3

para-xylene

B

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
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
67-56-1

methanol

108-88-3

toluene

A

95-47-6

o-xylene

B

106-42-3

para-xylene

C

108-38-3

m-xylene

Conditions
ConditionsYield
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;
67-56-1

methanol

108-88-3

toluene

106-42-3

para-xylene

Conditions
ConditionsYield
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;
589-18-4

4-Methylbenzyl alcohol

55-21-0

benzamide

A

106-42-3

para-xylene

B

65608-94-8

N-(p-methylbenzyl)benzamide

Conditions
ConditionsYield
With barium trifluoromethanesulfonate In toluene at 150℃; for 18h; Reagent/catalyst; Glovebox; Inert atmosphere;A 29%
B 72%
95-47-6

o-xylene

108-38-3

m-xylene

106-42-3

para-xylene

Conditions
ConditionsYield
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;
625-86-5

2,5-dimethylfuran

74-85-1

ethene

A

106-42-3

para-xylene

B

15329-10-9

3,6-dimethylcyclohex-2-enone

C

110-13-4

2,5-hexanedione

Conditions
ConditionsYield
With H-BEA-25 In 1,4-dioxane at 249.84℃; under 15001.5 Torr; for 4h; Diels-Alder Cycloaddition; Autoclave; chemoselective reaction;
2808-79-9

1,4-dimethylcyclohex-1-ene

106-42-3

para-xylene

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

Community Right-To-Know List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 100 ppm; STEL 150 ppm
ACGIH TLV: TWA 100 ppm; STEL 150 ppm; BEI: methyl hippuric acids in urine at end of shift 1.5 g/g creatinine; Not Classifiable as a Human Carcinogen
NIOSH REL: (Xylene) TWA 100 ppm; CL 200 ppm/10M

Specification

The 1,4-Dimethylbenzene, also called p-Xylene, is an aromatic hydrocarbon. It is an isomer of xylene. Other isomers include o-xylene and m-xylene. It occurs in two forms, either as colorless liquid with a characteristic aromatic odor at normal temperature, or as colorless crystalline solid below 13 °C. 1,4-Dimethylbenzene which exists in the atomatic tobacco and smoke is non-corrosive to metal. When heating to its decomposition, it decomposes to methane, hydrogen, toluene, couplet toluene and 2,6 - dimethyl anthracene.

Preparation: There is a considerable amount of 1,4-Dimethylbenzene in oil xylene and coal tar xylene. As the difference of boiling point between m-xylene and 1,4-Dimethylbenzene is only 0.75 °C, it can not be separated by distillation method. The current methods in domestic and foreign research are low-temperature crystallization separation, adsorption separation and complexing separation. The yield of low-temperature crystallization separation is 60-70% which is low. But the adsorption separation has relatively high yield and purity.

There is another method which has high purity of 99.9%. In transalkylation reactor, raw material toluene can produce xylene and benzene by alkyl transfer reaction. Part of m-xylene can be isomerized to 1,4-Dimethylbenzene by isomerization reactor. Then after some treatment, people can get the product with by-product m-xylene.

Uses: It is not only used as raw material in the production of polyester fibers and resins, paints, dyes and pesticides, but also used as chromatography standard materials and solvents. On a large scale, 1,4-Dimethylbenzene is used for the manufacture of terephthalic acid for polyester. In addition, it also can be used in organic synthesis. For example: it can react with benzoyl chloride to get 2,5-dimethyl-benzophenone. This reaction needs reagents CS2 and AlCl3.

1,4-Dimethylbenzene can react with benzoyl chloride to get 2,5-dimethyl-benzophenone

Safty: It has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) So 1,4-Dimethylbenzene should be sealed in the container and stored in the cool and dry place which must be away from oxidant.

Other physical properties: (1)ACD/LogP: 3.25; (2)ACD/LogD (pH 5.5): 3.247; (3)ACD/LogD (pH 7.4): 3.247; (4)ACD/BCF (pH 5.5): 173.006; (5)ACD/BCF (pH 7.4): 173.006; (6)ACD/KOC (pH 5.5): 1391.912; (7)ACD/KOC (pH 7.4): 1391.912; (8)Index of Refraction: 1.5; (9)Molar Refractivity: 35.903 cm3; (10)Molar Volume: 121.984 cm3; (11)Surface Tension: 28.791 dyne/cm; (12)Density: 0.87 g/cm3; (13)Flash Point: 27.222 °C; (14)Enthalpy of Vaporization: 35.67 kJ/mol; (15)Boiling Point: 139.61 °C at 760 mmHg; (16)Vapour Pressure: 7.943 mmHg at 25°C.

Data structure conversion:
(1)Canonical SMILES: CC1=CC=C(C=C1)C
(2)InChI: InChI=1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3

Toxicity: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC inhalation > 8350ppm/4H (8350ppm) BEHAVIORAL: TREMOR

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0556752,
mammal (species unspecified) LDLo intraperitoneal 2gm/kg (2000mg/kg)   Journal of Pathology and Bacteriology. Vol. 46, Pg. 95, 1938.
mammal (species unspecified) LDLo subcutaneous 5gm/kg (5000mg/kg)   Journal of Pathology and Bacteriology. Vol. 46, Pg. 95, 1938.
mouse LCLo inhalation 15gm/m3 (15000mg/m3) BEHAVIORAL: GENERAL ANESTHETIC

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 143, Pg. 223, 1929.
mouse LD50 intraperitoneal 2450uL/kg (2.45mL/kg)   Archives of Toxicology. Vol. 58, Pg. 106, 1985.
rat LC50 inhalation 4550ppm/4H (4550ppm) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

LIVER: OTHER CHANGES

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
"Biological Reactive Intermediates, Formation, Toxicity and Inactivation, Proceedings of the International Conference, Turku, Finland, 1975," Jollow, D.J., et al., eds., New York, Plenum Pub. Corp., 1977Vol. -, Pg. 302, 1977.
rat LD50 intraperitoneal 3810mg/kg (3810mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)

LIVER: OTHER CHANGES
"Biological Reactive Intermediates, Formation, Toxicity and Inactivation, Proceedings of the International Conference, Turku, Finland, 1975," Jollow, D.J., et al., eds., New York, Plenum Pub. Corp., 1977Vol. -, Pg. 302, 1977.
rat LD50 oral 5gm/kg (5000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 883, 1980.