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1,4-Dimethoxybenzene

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Name

1,4-Dimethoxybenzene

EINECS 205-771-9
CAS No. 150-78-7 Density 1.005 g/cm3
PSA 18.46000 LogP 1.70380
Solubility 0.8 g/l (20 ºC) in water Melting Point 55-58 ºC
Formula C8H10O2 Boiling Point 212.6 °C at 760 mmHg
Molecular Weight 138.166 Flash Point 73.5 °C
Transport Information N/A Appearance white crystals or powder
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 150-78-7 (1,4-Dimethoxybenzene) Hazard Symbols IrritantXi
Synonyms

Anisole, p-methoxy-;1, 3-Bis(hydroxymethyl)-2-benzimidazolinone;Benzene, 1,4-dimethoxy-;2-Benzimidazolinone, 1,3-bis(hydroxymethyl)-;Methyl p-methoxyphenyl ether;1,4-Dimethoxybenzol;Benzene, p-dimethoxy-;Hydroquinone dimethyl ether;Dimethyl hydroquinone;

Article Data 182

1,4-Dimethoxybenzene Synthetic route

1200-06-2

4-methoxyphenyl acetate

74-88-4

methyl iodide

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 1.) 0 deg C, 1 h, 2.) 25 deg C;98%
123-31-9

hydroquinone

74-88-4

methyl iodide

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 25℃; for 1h;97%
With potassium hydroxide; tetrabutylammomium bromide at 40℃; for 24h;96%
With potassium hydroxide
67-56-1

methanol

696-62-8

para-iodoanisole

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With N,N-dimethylglycine hydrochoride; caesium carbonate; copper(l) iodide at 110℃; for 24h; Ullmann coupling reaction;97%
With caesium carbonate In neat (no solvent) at 110℃; for 24h; Inert atmosphere; Sealed tube;91%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate at 110℃; for 23h;88%
67-56-1

methanol

623-12-1

4-chloromethoxybenzene

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; sodium t-butanolate In 1,4-dioxane at 80℃; for 20h; Concentration; Reagent/catalyst; Solvent; Temperature; Sealed tube; Inert atmosphere;96%
150-76-5

4-methoxy-phenol

77-78-1

dimethyl sulfate

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With sodium hydroxide; N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide In 1,2-dichloro-ethane for 6h; Heating;95%
With tetrabutylammomium bromide; sodium hydroxide In diethoxymethane; water at 50 - 55℃; for 4h;86%
With potassium hydroxide In methanol at 20℃; Cooling with ice;82%
With aluminum oxide; potassium hydroxide for 7h; microwave irradiation;68%
With sodium hydroxide
150-76-5

4-methoxy-phenol

18107-18-1

diazomethyl-trimethyl-silane

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile for 15h; Ambient temperature;93%
104-92-7

1-bromo-4-methoxy-benzene

107-31-3

Methyl formate

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With copper(I) bromide In methanol; sodium methylate93%
123-31-9

hydroquinone

77-78-1

dimethyl sulfate

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;92%
Stage #1: hydroquinone With potassium carbonate In acetone for 0.25h;
Stage #2: dimethyl sulfate In acetone for 24h; Reflux;
92%
With aluminum oxide; potassium hydroxide for 5h; microwave irradiation;87%
123-31-9

hydroquinone

616-38-6

carbonic acid dimethyl ester

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 170℃; for 1h; Microwave irradiation; Green chemistry;90%
With tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 160℃; under 15001.5 Torr; for 1h; Reagent/catalyst; Time; Temperature; Microwave irradiation;71%
598-99-2

Methyl trichloroacetate

150-76-5

4-methoxy-phenol

150-78-7

1,4-dimethoxybezene

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate at 150℃; for 2h;88%

1,4-Dimethoxybenzene Consensus Reports

Reported in EPA TSCA Inventory.

1,4-Dimethoxybenzene Specification

The IUPAC name of p-Dimethoxybenzene is 1,4-dimethoxybenzene. With the CAS registry number 150-78-7, it is also named as Hydroquinone dimethyl ether. The product's categories are aromatic ethers; benzene derivates. It is white crystals or powder with alfalfa-like aroma and phenol smell. And it appears to attract bees as it has a powerful response in their antenna. In addition, p-Dimethoxybenzene can be obtained by the reaction of p-Dimethoxybenzene and paradioxybenzene at the present of alkali. Furthermore, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.1; (4)ACD/LogD (pH 7.4): 2.1; (5)ACD/BCF (pH 5.5): 23.19; (6)ACD/BCF (pH 7.4): 23.19; (7)ACD/KOC (pH 7.4): 330.27; (8)#H bond acceptors: 2; (9)#H bond donors: 0; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.488; (12)Molar Refractivity: 39.6 cm3; (13)Molar Volume: 137.4 cm3; (14)Polarizability: 15.7×10-24 cm3; (15)Surface Tension: 29.6 dyne/cm; (16)Enthalpy of Vaporization: 43.06 kJ/mol; (17)Vapour Pressure: 0.25 mmHg at 25°C; (18)Rotatable Bond Count: 2; (19)Exact Mass: 138.06808; (20)MonoIsotopic Mass: 138.06808; (21)Topological Polar Surface Area: 18.5; (22)Heavy Atom Count: 10; (23)Complexity: 73.3.

Uses of p-Dimethoxybenzene: It is used in some paints and as a diazo dye. And it is used in perfumes and flavors in order to its floral odor. In addition, it is used on greasy skin, and with sulfur to treat acne, or as a dandruff treatment. Moreover, this chemical can be used as pharmaceutical intermediate. For example: it react with succinic acid anhydride to get 4-(2,5-dimethoxy-phenyl)-4-oxo-butyric acid. This reaction needs reagent AlCl3 by heating. The yield is 88%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. so people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. Smiles:c1(ccc(OC)cc1)OC
2. InChI:InChI=1/C8H10O2/c1-9-7-3-5-8(10-2)6-4-7/h3-6H,1-2H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 4gm/kg (4000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 4(2), Pg. 30, 1960.
rat LD50 oral 3600mg/kg (3600mg/kg)   Food and Cosmetics Toxicology. Vol. 16, Pg. 715, 1978.

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