Conditions | Yield |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile for 15h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With copper(I) bromide In methanol; sodium methylate | 93% |
Conditions | Yield |
---|---|
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 |
---|---|
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 |
---|---|
With 18-crown-6 ether; potassium carbonate at 150℃; for 2h; | 88% |
2,5-dimethoxyphenylboronic acid
1,4-dimethoxybezene
Conditions | Yield |
---|---|
With sodium hypochlorite; tetrabutylammomium bromide; water at 100℃; for 12h; Reagent/catalyst; | 88% |
N,N-dimethyl-formamide dimethyl acetal
4-methoxy-phenol
1,4-dimethoxybezene
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 140℃; for 1h; Microwave irradiation; | 87% |
Conditions | Yield |
---|---|
With rhodium(II) acetate; 1,3-bis-(diphenylphosphino)propane In toluene at 200℃; under 7500.75 Torr; Inert atmosphere; | 87% |
methanol
para-diiodobenzene
A
1-fluoro-4-methoxybenzene
B
iodobenzene
C
4-fluoro-1-iodobenzene
D
4-methoxy-phenol
E
1,4-dimethoxybezene
Conditions | Yield |
---|---|
With sodium chloride; teflon In water; acetonitrile for 0.0333333h; Irradiation; | A 4.82% B 86.23% C 1.9% D 3.22% E 0.44% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 140℃; for 1h; Microwave irradiation; | 84% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile for 5h; Heating; | 83% |
With sodium hydroxide In N,N-dimethyl acetamide at 65℃; Rate constant; also in KF-cryptand 222 system; | |
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant; |
Conditions | Yield |
---|---|
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction; | 82% |
With N-butyl-4-methylpyridinium bromide at 170℃; for 2h; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction; | 75% |
With C21H22INSn; potassium carbonate at 200℃; for 6h; | |
With leucine intercalated Mg-Al layered double hydorxide at 180℃; for 6h; Autoclave; Green chemistry; chemoselective reaction; | 91 %Chromat. |
Conditions | Yield |
---|---|
With boron nitride In isopropyl alcohol at 20℃; for 15h; | 82% |
sodium methylate
1-Bromo-4-fluorobenzene
A
1-fluoro-4-methoxybenzene
B
1,4-dimethoxybezene
Conditions | Yield |
---|---|
copper(I) bromide In methanol Product distribution; Heating; | A 80% B n/a |
copper(I) bromide In methanol for 4h; Heating; | A 80% B n/a |
Conditions | Yield |
---|---|
With potassium carbonate In 1,2-dimethoxyethane at 145℃; for 1h; Microwave irradiation; Inert atmosphere; Sealed vessel; | 78% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In N,N-dimethyl-formamide at 100℃; Inert atmosphere; | A 22% B 78% |
Conditions | Yield |
---|---|
With potassium In toluene at 111℃; for 12h; | 75% |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 130℃; for 16h; | 72% |
<(η-C6H6)(η-C5EtMe4)Rh>(2+)*2 In nitromethane at 80℃; for 96h; | 47 % Chromat. |
methanol
4-chloromethoxybenzene
benzene
A
4-methoxylbiphenyl
B
methoxybenzene
C
1,4-dimethoxybezene
Conditions | Yield |
---|---|
With acetone Product distribution; Further Variations:; nonsensitized irradiation; UV-irradiation; | A 71% B 20% C 7% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In N,N-dimethyl-formamide at 100℃; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere; | 70% |
1,4-dimethoxy-2-phenylsulfanyl-benzene
A
thiophenol
B
diphenyldisulfane
C
1,4-dimethoxybezene
Conditions | Yield |
---|---|
In methanol for 1h; Irradiation; | A 9% B n/a C 68% |
Conditions | Yield |
---|---|
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere; | 68% |
Conditions | Yield |
---|---|
With oxygen; copper diacetate; silver carbonate In N,N-dimethyl-formamide at 140℃; under 760.051 Torr; for 36h; | 66% |
Conditions | Yield |
---|---|
With caesium carbonate; copper(l) iodide at 110℃; for 24h; | 63% |
With indium(III) chloride; carbon monoxide; magnesium carbonate; cobalt acetylacetonate In acetone under 760.051 Torr; for 12h; Irradiation; | 94 % Chromat. |
Conditions | Yield |
---|---|
With Selectfluor; sodium chloride In acetonitrile at 20℃; for 113h; | 100% |
With N-chloro-succinimide; iron(III) chloride In acetonitrile for 0.5h; | 93% |
With aluminum oxide; sodium chlorite; (salen)Mn(III) In dichloromethane at 20℃; for 0.5h; | 92% |
1,4-dimethoxybezene
1,4-dimethoxycyclohexane
Conditions | Yield |
---|---|
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 160℃; under 37503.8 Torr; for 18h; | 100% |
With 1,4-dioxane; Pd/SrCO3 at 210℃; under 69873.3 Torr; Hydrogenation; | |
With hydrogen In water at 60℃; under 7500.75 Torr; for 24h; | 90 %Chromat. |
Conditions | Yield |
---|---|
With Nitrogen dioxide In dichloromethane in the dark; -78 deg C, 2 min; RT, 15 min; | 100% |
With Nitrogen dioxide In dichloromethane at -78℃; | 100% |
With benzyltriphenylphosphonium nitrate; Methanesulfonic anhydride at 20℃; for 0.0833333h; | 100% |
1,4-dimethoxybezene
1-bromo-2,5-dimethoxybenzene
Conditions | Yield |
---|---|
With (CH3)4Br In liquid sulphur dioxide at -23℃; Rate constant; | 100% |
With (CH3)4Br In liquid sulphur dioxide at -23℃; | 100% |
With Selectfluor; sodium bromide In acetonitrile at 20℃; for 113h; | 100% |
6-methyl-6,7-dihydro-7-hydroxy-5H-pyrrolo<3,4-b>pyridin-5-one
1,4-dimethoxybezene
7-(2,5-Dimethoxy-phenyl)-6-methyl-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one
Conditions | Yield |
---|---|
With trifluoroacetic acid at 73℃; for 1h; | 100% |
1,4-dimethoxybezene
Diethyl ketomalonate
diethyl (2,5-dimethoxyphenyl)tartronate
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane 1.) 0 deg C, 10 min, 2.) 20 deg C, 19 h; | 100% |
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene In methanol; water at 20℃; for 4h; | 100% |
With manganese dioxide impregnated with nitric acid In dichloromethane for 1.5h; Ambient temperature; | 93% |
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 1h; | 86% |
Conditions | Yield |
---|---|
With trifluoroacetic acid; trifluoroacetic anhydride for 12h; Acylation; Heating; | 100% |
With TFFA In trifluoroacetic acid Acylation; | 98% |
With trifluoroacetic acid; trifluoroacetic anhydride for 12h; Friedel-Crafts Acylation; Inert atmosphere; Reflux; | 98% |
1,4-dimethoxybezene
1,1,4,4-tetrakis(trimethylsilyl)butane-1,4-diylsilylene
Conditions | Yield |
---|---|
Irradiation; | 100% |
Dichloromethyl methyl ether
1,4-dimethoxybezene
2,5-dimethoxybenzaldehyde
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 0℃; | 100% |
With titanium tetrachloride In dichloromethane at -5 - 20℃; for 1.5h; Reagent/catalyst; Temperature; Inert atmosphere; | 97.6% |
With titanium tetrachloride In dichloromethane at 20℃; for 0.25h; |
2-Fluorobenzoyl chloride
1,4-dimethoxybezene
A
benzophenone
B
2-methoxy-9H-xanthen-9-one
Conditions | Yield |
---|---|
With hydrogenchloride In AlCl3; 1,2-dichloro-ethane | A n/a B 100% |
dichloromaleic acid anhydride
1,4-dimethoxybezene
2,3-dichloro-5,8-dihydroxy-[1,4]naphthoquinone
Conditions | Yield |
---|---|
Stage #1: dichloromaleic acid anhydride; 1,4-dimethoxybezene With aluminum (III) chloride; sodium chloride In neat (no solvent) at 140 - 175℃; for 0.0833333h; Stage #2: With hydrogenchloride; water at 20℃; | 99% |
Stage #1: dichloromaleic acid anhydride; 1,4-dimethoxybezene With aluminum (III) chloride; sodium chloride In neat (no solvent) at 180℃; for 0.0333333h; Friedel-Crafts Acylation; Stage #2: With hydrogenchloride; water Friedel-Crafts Acylation; | 97% |
With aluminum (III) chloride; sodium chloride at 150 - 170℃; for 0.166667h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide In methanol Bromination; Heating; | 99% |
With tert.-butylhydroperoxide; hydrogen bromide In methanol for 6h; Heating; | 98% |
With bromine In dichloromethane at 2 - 4℃; for 2.83333h; Inert atmosphere; Large scale; | 98.6% |
2-(3,3-dimethyl-1-butynyl)phenyl isothiocyanate
1,4-dimethoxybezene
A
4-(2,5-dimethoxyphenyl)-2(1H)-quinolinethione
B
1,4-dimethoxy-2-tert-butylbenzene
Conditions | Yield |
---|---|
With indium(III) bromide at 150℃; for 1h; | A 99% B 20% |
Ethyl oxalyl chloride
1,4-dimethoxybezene
2,5-dimethoxyphenylglyoxylic acid ethyl ester
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 20℃; for 1h; Friedel-Crafts acylation; | 98% |
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 2h; | 55% |
With carbon disulfide; aluminium trichloride | |
With aluminium trichloride In dichloromethane at -10 - 25℃; |
Conditions | Yield |
---|---|
With aluminum (III) chloride Friedel Crafts acylation; | 98% |
With iron(III) oxide at 20℃; for 0.0833333h; Friedel Crafts acylation; regioselective reaction; | 96% |
With zinc oxide nanoparticles supported on polyaniline at 20℃; for 0.166667h; Friedel Crafts acylation; Neat (no solvent); | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Autoclave; Inert atmosphere; Green chemistry; | 98% |
With hydrogen iodide at 25℃; for 24h; Inert atmosphere; | 96% |
With lithium triethylborohydride In tetrahydrofuran at 67℃; for 168h; | 90% |
Conditions | Yield |
---|---|
With potassium hydroxide Ambient temperature; anodic oxidation (platinised titanium anode and bridged nickel cathode plates); | 98% |
With piperidine; silica gel Electrochemical reaction; | 88% |
With potassium hydroxide at 15 - 20℃; for 24h; electrolysis: platinum mesh anode, platinum sheet cathode; | 73% |
pentafluorobenzoyl peroxide
1,4-dimethoxybezene
A
Pentafluorobenzoic acid
B
2,3,4,5,6-Pentafluoro-benzoic acid 2,5-dimethoxy-phenyl ester
C
C22H8F10O6
Conditions | Yield |
---|---|
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 25℃; Product distribution; Rate constant; Mechanism; different starting concentration ratios; | A 98% B n/a C n/a |
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 25℃; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With aluminum oxide; methanesulfonic acid at 20℃; for 0.416667h; neat (no solvent); | 98% |
With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 2h; | 82% |
In formic acid; acetic acid Controlled potential electrolysis; chemoselective reaction; | 12% |
Conditions | Yield |
---|---|
With graphene oxide In chloroform at 100℃; for 15h; Friedel-Crafts Alkylation; Sealed tube; chemoselective reaction; | 98% |
With air; bismuth(III) chloride at 100℃; for 10h; | 89% |
iron(III) chloride at 80℃; for 4h; | 51% |
With iron(III) chloride at 80℃; for 4h; | 95 % Chromat. |
With iodine at 80℃; for 4h; Friedel-Crafts Reaction; | 95 % Chromat. |
dimethylmonochlorosilane
1,4-dimethoxybezene
(2,5-dimethoxyphenyl)dimethylsilane
Conditions | Yield |
---|---|
Stage #1: 1,4-dimethoxybezene With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: dimethylmonochlorosilane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 98% |
1,4-dimethoxybezene
1,4-dimethoxycyclohexa-1,4-diene
Conditions | Yield |
---|---|
With ammonia; lithium for 2h; | 97% |
With tert-Amyl alcohol; ethylenediamine In tetrahydrofuran at 0 - 5℃; for 24h; Birch reduction; Inert atmosphere; | 43% |
With diethyl ether; ethanol; ammonia weiteres Reagens: Natrium; | |
With propylamine; lithium; tert-butyl alcohol |
1,4-dimethoxybezene
1,4-diiodo-2,5-dimethoxybenzene
Conditions | Yield |
---|---|
With iodine; periodic acid In methanol at 70℃; for 4h; Inert atmosphere; | 97% |
With Barluenga reagent; trifluorormethanesulfonic acid In dichloromethane at 20℃; for 3h; | 96% |
With iodine; periodic acid In methanol for 4h; Reflux; | 94% |
1,4-dimethoxybezene
Conditions | Yield |
---|---|
With thionyl chloride; water at 20℃; for 0.0833333h; | 97% |
With thionyl chloride; scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 1.5h; | 95% |
With thionyl chloride; lithium perchlorate In tetrahydrofuran at 20℃; for 2.5h; | 89% |
With carbon disulfide; aluminium trichloride; sulfur dioxide at 0℃; |
6,7-Dihydro-7-hydroxy-5H-pyrrolo<3,4-b>pyridin-5-one
1,4-dimethoxybezene
7-(2,5-Dimethoxy-phenyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one
Conditions | Yield |
---|---|
With trifluoroacetic acid at 73℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With nitric acid; silica gel In dichloromethane for 0.0833333h; Product distribution; Ambient temperature; | A 97% B 2% |
Conditions | Yield |
---|---|
In acetic anhydride; trifluoroacetic acid at 95℃; for 1h; | 97% |
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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