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493-09-4

Basic Information
CAS No.: 493-09-4
Name: 1,4-Benzodioxane
Article Data: 47
Cas Database
Molecular Structure:
Molecular Structure of 493-09-4 (1,4-Benzodioxane)
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: IrritantXi
Risk Codes: N/A
Safety: 23-24/25
Transport Information: N/A
PSA: 18.46000
LogP: 1.45780
Synthetic route
4792-78-3

2-(2-hydroxy-phenoxy)-ethanol

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
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
120-80-9

benzene-1,2-diol

106-93-4

ethylene dibromide

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
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%
34743-89-0

2-(2-bromophenoxy)ethan-1-ol

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
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%
96-49-1

[1,3]-dioxolan-2-one

120-80-9

benzene-1,2-diol

A

493-09-4

benzo-1,4-dioxane

B

10234-40-9

2,2'-(1,2-phenylenedioxy)diethanol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 170℃; for 1h; Inert atmosphere; Schlenk technique;A 5%
B 84%
52287-51-1

6-bromo-1,4-benzodioxane

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
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%
120-80-9

benzene-1,2-diol

(vinylselenonyl)benzene

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
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%
3663-82-9

2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
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%
107-21-1

ethylene glycol

583-53-9

1,2-dibromobenzene

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h;65%
107-21-1

ethylene glycol

95-50-1

1,2-dichloro-benzene

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h;63%
120-80-9

benzene-1,2-diol

107-06-2

1,2-dichloro-ethane

493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide57%
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
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Chemistry

Molecular Formula: C8H8O2
Formula Weight: 136.15
bp of 1,4-Benzodioxan (493-09-4): 103 °C 6 mm Hg(lit.)
density : 1.142 g/mL at 25 °C(lit.)
refractive index : n20/D 1.549(lit.)
Fp of 1,4-Benzodioxan (493-09-4): 190 °F
Solubility: Insoluble in water; soluble in all typical organic solvents
Appearance: Colorless to light yellow liquid
Odor of 1,4-Benzodioxan (493-09-4): Aromatic odor

Uses

1,4-Benzodioxan (493-09-4) can be used as the intermediate of doxazosin.

Toxicity Data With Reference

LD50/LC50: RTECS: Not available
Carcinogenicity: 1,4-Benzodioxan (493-09-4) - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.

Safety Profile

Hazard Codes : Xi (Irritant)
Safety Statements : 23-24/25 (Toxic by inhalation; Toxic in contact with skin and if swallowed)
WGK Germany : 3
RTECS : DF4728000
Hazard Note : Irritant
HS Code : 29329995

Standards and Recommendations

Purity: 98.0%

Specification

Storage: Store in a tightly closed container. Store in a cool, dry place. Keep away from sources of ignition.
Handling: Avoid contact with skin and eyes. Avoid breathing dust, vapor, mist, or gas. Keep container tightly closed. Wash thoroughly after handling. Mechanical exhaust required.