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CAS No.: | 150-78-7 |
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Name: | 1,4-Dimethoxybenzene |
Article Data: | 182 |
Molecular Structure: | |
Formula: | C8H10O2 |
Molecular Weight: | 138.166 |
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; |
EINECS: | 205-771-9 |
Density: | 1.005 g/cm3 |
Melting Point: | 55-58 ºC |
Boiling Point: | 212.6 °C at 760 mmHg |
Flash Point: | 73.5 °C |
Solubility: | 0.8 g/l (20 ºC) in water |
Appearance: | white crystals or powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36-24/25 |
PSA: | 18.46000 |
LogP: | 1.70380 |
Conditions | Yield |
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With sodium hydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 1.) 0 deg C, 1 h, 2.) 25 deg C; | 98% |
Conditions | Yield |
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With potassium hydroxide In dimethyl sulfoxide at 25℃; for 1h; | 97% |
With potassium hydroxide; tetrabutylammomium bromide at 40℃; for 24h; | 96% |
With potassium hydroxide |
Conditions | Yield |
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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% |
Conditions | Yield |
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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% |
Conditions | Yield |
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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 |
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile for 15h; Ambient temperature; | 93% |
Conditions | Yield |
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With copper(I) bromide In methanol; sodium methylate | 93% |
Conditions | Yield |
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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% |
Conditions | Yield |
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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% |
Conditions | Yield |
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With 18-crown-6 ether; potassium carbonate at 150℃; for 2h; | 88% |
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. |