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CAS No.: | 493-09-4 |
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Name: | 1,4-Benzodioxan |
Article Data: | 47 |
Molecular Structure: | |
Formula: | C8H8O2 |
Molecular Weight: | 136.15 |
Synonyms: | 1,4-Benzodioxan(6CI,7CI,8CI);1,2-(Ethylenedioxy)benzene;2,3-Dihydro-1,4-benzodioxin;2,3-Dihydrobenzo[1,4]dioxine;Benzene, 1,2-[1,2-ethanediylbis(oxy)]-;Ethyleneo-phenylene dioxide;NSC 406705;Pyrocatechol ethylene ether; |
EINECS: | 207-775-6 |
Density: | 1.15 g/cm3 |
Melting Point: | 213-217 °C |
Boiling Point: | 248.138 °C at 760 mmHg |
Flash Point: | 87.778 °C |
Solubility: | insoluble in water |
Appearance: | clear colourless to very slightly yellow liquid |
Hazard Symbols: | Xi |
Safety: | 23-24/25 |
PSA: | 18.46000 |
LogP: | 1.45780 |
Conditions | Yield |
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With 1,4-diaza-bicyclo[2.2.2]octane for 3h; Reflux; | 97% |
With 1,4-diaza-bicyclo[2.2.2]octane; carbonic acid dimethyl ester at 90℃; for 2h; Reagent/catalyst; Time; | 92% |
With phosphorus pentoxide | |
Multi-step reaction with 2 steps 1: pyridine; PBr3 2: aqueous alkaline solution View Scheme |
Conditions | Yield |
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With sodium hydroxide; (C16H33CH3)2NCH2CH2N(CH3)2C16H33)(2+)*Br(1-)*Br(1-) In water Heating; | 89% |
With sodium hydroxide; (C16H33N(CH3)2CH2CH=CHCH2(CH3)2NC16H33)(2+)*Br(1-)*Br(1-) In water Heating; | 84% |
With potassium carbonate In ethylene glycol; ethyl acetate Reflux; | 81% |
2-(2-bromophenoxy)ethan-1-ol
benzo-1,4-dioxane
Conditions | Yield |
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With palladium diacetate; 9-di(2-tert-butylphosphinophenyl)phenanthrene; caesium carbonate In toluene at 70℃; for 40h; | 88% |
With palladium diacetate; caesium carbonate; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine In toluene at 70℃; for 40h; | 88% |
With (4,4′-di-tert-butyl-2,2′-dipyridyl)Ni(o-tolyl)(Br); 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 80℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation; | 86% |
[1,3]-dioxolan-2-one
benzene-1,2-diol
A
benzo-1,4-dioxane
B
2,2'-(1,2-phenylenedioxy)diethanol
Conditions | Yield |
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With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 170℃; for 1h; Inert atmosphere; Schlenk technique; | A 5% B 84% |
6-bromo-1,4-benzodioxane
benzo-1,4-dioxane
Conditions | Yield |
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With tetrabutylammonium tetrafluoroborate; triethylamine In tetrahydrofuran; acetonitrile at 20℃; for 4.4h; Inert atmosphere; Electrolysis; | 83% |
With isopropyl alcohol for 20h; Schlenk technique; Inert atmosphere; Irradiation; Heating; | 65% |
Conditions | Yield |
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Stage #1: benzene-1,2-diol With caesium carbonate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (vinylselenonyl)benzene In dichloromethane at 0 - 20℃; for 24h; Reagent/catalyst; Temperature; Time; Inert atmosphere; | 80% |
Conditions | Yield |
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With chlorobis(cyclooctene)-iridium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride In water; 1,3,5-trimethyl-benzene at 170℃; for 60h; Schlenk technique; Inert atmosphere; | 79% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride In water; 1,3,5-trimethyl-benzene for 60h; Reflux; | 79% |
Conditions | Yield |
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With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h; | 65% |
Conditions | Yield |
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With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h; | 63% |
Conditions | Yield |
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With sodium hydroxide In dimethyl sulfoxide | 57% |
With sodium hydroxide In N,N-dimethyl-formamide at 90℃; | 2.1 g |
With sodium hydroxide In dimethyl sulfoxide at 80 - 85℃; for 5.45h; | 115 g |