Product Name

  • Name

    1,4-Benzodioxan

  • EINECS 207-775-6
  • CAS No. 493-09-4
  • Article Data47
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility insoluble in water
  • Melting Point 213-217 °C
  • Formula C8H8O2
  • Boiling Point 248.138 °C at 760 mmHg
  • Molecular Weight 136.15
  • Flash Point 87.778 °C
  • Transport Information
  • Appearance clear colourless to very slightly yellow liquid
  • Safety 23-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 493-09-4 (1,4-Benzodioxan)
  • Hazard Symbols IrritantXi
  • 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;
  • PSA 18.46000
  • LogP 1.45780

Synthetic route

2-(2-hydroxy-phenoxy)-ethanol
4792-78-3

2-(2-hydroxy-phenoxy)-ethanol

benzo-1,4-dioxane
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
benzene-1,2-diol
120-80-9

benzene-1,2-diol

ethylene dibromide
106-93-4

ethylene dibromide

benzo-1,4-dioxane
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%
2-(2-bromophenoxy)ethan-1-ol
34743-89-0

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

benzo-1,4-dioxane
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%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

benzene-1,2-diol
120-80-9

benzene-1,2-diol

A

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

B

2,2'-(1,2-phenylenedioxy)diethanol
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%
6-bromo-1,4-benzodioxane
52287-51-1

6-bromo-1,4-benzodioxane

benzo-1,4-dioxane
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%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

(vinylselenonyl)benzene

(vinylselenonyl)benzene

benzo-1,4-dioxane
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%
2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin
3663-82-9

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

benzo-1,4-dioxane
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%
ethylene glycol
107-21-1

ethylene glycol

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

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

ethylene glycol

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h;63%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

benzo-1,4-dioxane
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
2-fluorophenol
367-12-4

2-fluorophenol

2-chloro-ethanol
107-07-3

2-chloro-ethanol

A

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

B

2-hydroxyphenyl 2-chloroethyl ether
4792-79-4

2-hydroxyphenyl 2-chloroethyl ether

Conditions
ConditionsYield
With <(η-C6H6)Rh(η-C5EtMe4)>(2+)*2 In nitromethane at 80℃; for 48h; Title compound not separated from byproducts;A 50%
B 10 % Chromat.
2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

A

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

B

6-iodo-1,4-benzodioxane
57744-67-9

6-iodo-1,4-benzodioxane

C

2-(4-iodophenoxy)ethanol
29639-77-8

2-(4-iodophenoxy)ethanol

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; Irradiation;A 39%
B 12%
C n/a
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; Irradiation;A 6%
B 22%
C n/a
2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

A

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

B

6-iodo-1,4-benzodioxane
57744-67-9

6-iodo-1,4-benzodioxane

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; for 2h; Irradiation;A 39%
B 12%
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; for 2h; Irradiation;A 6%
B 22%
2-(2-fluorophenoxy)ethan-1-ol
2924-65-4

2-(2-fluorophenoxy)ethan-1-ol

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
(η5-ethyltetramethylcyclopentadienyl)(η6-benzene)rhodium(III) tetrafluoroborate In nitromethane; acetone at 80℃; for 312h;35%
2-(2-bromo-ethoxy)-phenol
51974-48-2

2-(2-bromo-ethoxy)-phenol

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With alkaline solution
With potassium hydroxide In water; dimethyl sulfoxide at 25℃;92 % Spectr.
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Rate constant;92 % Spectr.
1-(benzyloxy)-2-(2-bromoethoxy)benzene
154582-47-5

1-(benzyloxy)-2-(2-bromoethoxy)benzene

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With hydrogenchloride; ethanol
oxirane
75-21-8

oxirane

phenylium
17333-73-2

phenylium

A

1-benzofurane
271-89-6

1-benzofurane

B

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

C

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

D

vinyl phenyl ether
766-94-9

vinyl phenyl ether

Conditions
ConditionsYield
With oxygen; trimethylamine under 244 Torr; for 8760h; Ambient temperature; dark;A 4 % Chromat.
B 15 % Chromat.
C 3 % Chromat.
D 78 % Chromat.
With oxygen; trimethylamine under 244 Torr; for 8760h; Product distribution; Mechanism; Ambient temperature; arylation of various cyclic ethers in the dark and effects of base;A 4 % Chromat.
B 15 % Chromat.
C 3 % Chromat.
D 78 % Chromat.
oxirane
75-21-8

oxirane

phenylium
17333-73-2

phenylium

A

1-benzofurane
271-89-6

1-benzofurane

B

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

C

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

D

phenol
108-95-2

phenol

Conditions
ConditionsYield
With oxygen under 34 Torr; for 8760h; Ambient temperature; dark;A 2 % Chromat.
B 21 % Chromat.
C 61 % Chromat.
D 15 % Chromat.
oxirane
75-21-8

oxirane

phenylium
17333-73-2

phenylium

A

1-benzofurane
271-89-6

1-benzofurane

B

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

C

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

D

vinyl phenyl ether
766-94-9

vinyl phenyl ether

E

phenol
108-95-2

phenol

Conditions
ConditionsYield
With oxygen under 34 Torr; for 8760h; Product distribution; Mechanism; Ambient temperature; arylation of various cyclic ethers in the dark;A 2 % Chromat.
B 21 % Chromat.
C 61 % Chromat.
D 1 % Chromat.
E 15 % Chromat.
oxirane
75-21-8

oxirane

phenylium
17333-73-2

phenylium

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
With oxygen under 224 Torr; for 8760h; Ambient temperature; dark;A 37 % Chromat.
B 33 % Chromat.
C 30 % Chromat.
ethylene glycol
107-21-1

ethylene glycol

cyclohexane-1,2-dione
765-87-7

cyclohexane-1,2-dione

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride In benzene Heating;50 % Chromat.
2-fluorophenol
367-12-4

2-fluorophenol

2-chloro-ethanol
107-07-3

2-chloro-ethanol

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With <(η-C6H6)Rh(η-C5EtMe4)>(2+)*2; triethylamine 1) CH3NO2, 80 deg C, 2 d, 2) room temperature, 24 h; Yield given. Multistep reaction. Title compound not separated from byproducts;
ethyleneglycol sulfate
1072-53-3

ethyleneglycol sulfate

benzene-1,2-diol
120-80-9

benzene-1,2-diol

aqueous alkali

aqueous alkali

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

1,10-Dimethyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene
110851-22-4

1,10-Dimethyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 1 h / -78 °C / Irradiation
2: potassium carbonate / ethane-1,2-diol / 4 h / 120 °C
View Scheme
2,9,11,12,13-Pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene
110851-16-6

2,9,11,12,13-Pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / CH2Cl2 / 1 h / -78 °C / Irradiation
2: potassium carbonate / ethane-1,2-diol / 4 h / 120 °C
View Scheme
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1,2-bis<2-(-p-toluenesulfonyloxy)ethoxy>amine

1,2-bis<2-(-p-toluenesulfonyloxy)ethoxy>amine

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous NaOH
2: phosphorus (V)-oxide
View Scheme
Multi-step reaction with 3 steps
1: sodium ethylate; ethanol
2: pyridine; PBr3
3: aqueous alkaline solution
View Scheme
2,3-dibromo-2,3-dihydro-benzo[1,4]dioxin
67470-89-7

2,3-dibromo-2,3-dihydro-benzo[1,4]dioxin

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
With sodium iodide In acetone for 2h; Heating / reflux;
2-(2-hydroxy-phenoxy)-ethanol
4792-78-3

2-(2-hydroxy-phenoxy)-ethanol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

B

C10H12O5

C10H12O5

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 90℃; for 24h;A 10 %Chromat.
B 90 %Chromat.
benzene-1,2-diol
120-80-9

benzene-1,2-diol

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 150 °C / Autoclave
2: 1,4-diaza-bicyclo[2.2.2]octane / 3 h / Reflux
View Scheme
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

6-bromo-1,4-benzodioxane
52287-51-1

6-bromo-1,4-benzodioxane

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h;100%
With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 24h;100%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

benzyl alcohol
100-51-6

benzyl alcohol

6-Benzyl-2,3-dihydro-benzo[1,4]dioxine

6-Benzyl-2,3-dihydro-benzo[1,4]dioxine

Conditions
ConditionsYield
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4;100%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

tert-butyl alcohol
75-65-0

tert-butyl alcohol

6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine
93591-46-9

6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine

Conditions
ConditionsYield
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4;100%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

2-bromo-5-iodobenzoyl chloride
1261570-98-2

2-bromo-5-iodobenzoyl chloride

(2-bromo-5-iodophenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone
1291094-64-8

(2-bromo-5-iodophenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃; for 3h; Temperature;100%
With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 4h; Inert atmosphere;90%
In dichloromethane at 0 - 20℃;
2-chloro-5-iodobenzoylchloride
281652-58-2

2-chloro-5-iodobenzoylchloride

benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

(2-chloro-5-iodophenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone

(2-chloro-5-iodophenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃; for 16h;98.7%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

2,3-dihydro-benzo[1,4]dioxin-6-sulfonic acid
127461-51-2

2,3-dihydro-benzo[1,4]dioxin-6-sulfonic acid

Conditions
ConditionsYield
With sulfur trioxide In 1,4-dioxane-d8 at 15℃; for 0.25h; other time; other temp; other reagent: cc H2SO4;98%
With sulfuric acid at 125℃;
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

2,3-Dihydro-benzo[1,4]dioxine-5,7-disulfonic acid

2,3-Dihydro-benzo[1,4]dioxine-5,7-disulfonic acid

Conditions
ConditionsYield
With sulfur trioxide In nitromethane at 10℃; for 0.25h; other reagent;98%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

5-bromo-2-methylbenzoyl chloride
21900-41-4

5-bromo-2-methylbenzoyl chloride

(5-bromo-2-methylphenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone

(5-bromo-2-methylphenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃; Inert atmosphere;96%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h;95%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

2-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)benzo[d]thiazole
1556673-47-2

2-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)benzo[d]thiazole

Conditions
ConditionsYield
With di-tert-butyl peroxide; copper diacetate In acetonitrile at 120℃; for 6h; Inert atmosphere;94%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

chloroethane
75-00-3

chloroethane

6-ethylbenzodioxane

6-ethylbenzodioxane

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h;93.1%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

benzoyl chloride
98-88-4

benzoyl chloride

2,3-dihydro-1,4-benzodioxin-6-yl(phenyl)methanone
93637-87-7

2,3-dihydro-1,4-benzodioxin-6-yl(phenyl)methanone

Conditions
ConditionsYield
With aluminium trichloride In nitrobenzene at 5℃; for 6h;92.9%
With aluminium trichloride In 1,2-dichloro-ethane at 20℃; for 10h;88%
With aluminium trichloride In dichloromethane at 0℃; for 1h;85%
With aluminium trichloride In dichloromethane at 15℃; for 1h;
With aluminium trichloride In benzene at 55 - 60℃; for 2.5h; Friedel-Crafts reaction;
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

acetyl chloride
75-36-5

acetyl chloride

1,4-benzodioxan-6-yl methyl ketone
2879-20-1

1,4-benzodioxan-6-yl methyl ketone

Conditions
ConditionsYield
92%
With aluminium trichloride In carbon disulfide for 10h; Ambient temperature;91%
With aluminium trichloride In benzene at 55 - 60℃; for 2.5h; Friedel-Crafts reaction;
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

tertiary butyl chloride
507-20-0

tertiary butyl chloride

6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine
93591-46-9

6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h;91.2%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

6,7-dibromo-2,3-dihydrobenzo[b][1,4]dioxine
25812-80-0

6,7-dibromo-2,3-dihydrobenzo[b][1,4]dioxine

Conditions
ConditionsYield
With bromine In dichloromethane at 20℃;90%
With bromine In dichloromethane at 20℃; Inert atmosphere;83%
With iodine pentoxide; potassium bromide In water at 20℃; for 23h; regioselective reaction;78%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

4-fluorobenzoyl chloride
403-43-0

4-fluorobenzoyl chloride

(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-(4-fluoro-phenyl)-methanone
101018-97-7

(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-(4-fluoro-phenyl)-methanone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 15℃; for 1h;90%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

(4-Bromo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone
101018-99-9

(4-Bromo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 15℃; for 1h;90%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

1,5-Hexadien
592-42-7

1,5-Hexadien

C20H28O2

C20H28O2

Conditions
ConditionsYield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 2h; stereoselective reaction;90%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

6-(3,4,5-trimethoxybenzoyl)-2,3-dihydro-1,4-benzodioxin
126382-18-1

6-(3,4,5-trimethoxybenzoyl)-2,3-dihydro-1,4-benzodioxin

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane for 24h; Ambient temperature;88%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

2,3,10,11-tetrahydro[1,4]dioxino[2',3':8,9][1,2,5,6]benzotetrathiocino[3,4-g][1,4]benzodioxine

2,3,10,11-tetrahydro[1,4]dioxino[2',3':8,9][1,2,5,6]benzotetrathiocino[3,4-g][1,4]benzodioxine

Conditions
ConditionsYield
With disulfur dichloride; acetic acid at 20℃; for 120h; Inert atmosphere; Schlenk technique; Glovebox;88%
With disulfur dichloride In acetic acid for 18h;52%
Stage #1: benzo-1,4-dioxane With disulfur dichloride In acetic acid at 20℃; for 48h;
Stage #2: With tin(ll) chloride In methanol; acetic acid
With disulfur dichloride; acetic acid at 20℃; Inert atmosphere; Schlenk technique;2.45 g
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

n-Butyl chloride
109-69-3

n-Butyl chloride

C12H16O2

C12H16O2

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h;87.5%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

6-nitro-2,3-dihydrobenzo[b][1,4]dioxine
16498-20-7

6-nitro-2,3-dihydrobenzo[b][1,4]dioxine

Conditions
ConditionsYield
With nitric acid at 60℃;87%
With tert.-butylnitrite In acetonitrile at 20℃; for 1h;80%
With nitric acid In water at 20 - 80℃; for 6h;76.7%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

norbornene
498-66-8

norbornene

5,8-bis(bicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1,4-benzodioxine

5,8-bis(bicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1,4-benzodioxine

Conditions
ConditionsYield
With (C5H5)Y(CH2C6H4NMe2-o)2; trityl tetrakis(pentafluorophenyl)borate In toluene at 70℃; for 24h; Inert atmosphere; Glovebox; regioselective reaction;87%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

formaldehyd
50-00-0

formaldehyd

6,7-bis(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine

6,7-bis(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine

Conditions
ConditionsYield
Stage #1: benzo-1,4-dioxane; formaldehyd With acetic acid at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With hydrogen bromide; acetic acid at 0 - 20℃; Inert atmosphere;
87%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

6-iodo-1,4-benzodioxane
57744-67-9

6-iodo-1,4-benzodioxane

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate; carbon dioxide; iodine; oxygen In ethylene glycol at 100℃; under 5250.53 - 9000.9 Torr; for 10h; Autoclave; Green chemistry; regioselective reaction;86%
With iodine; periodic acid In ethanol for 0.75h; Heating;73%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

(2,3-dihydro-1,4-benzodioxin-6-yl)phosphonic diethylester

(2,3-dihydro-1,4-benzodioxin-6-yl)phosphonic diethylester

Conditions
ConditionsYield
With manganese(III) triacetate dihydrate In acetic acid at 60℃; for 5h;85%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

C23H19BrO4

C23H19BrO4

Conditions
ConditionsYield
With Amberlyst-15 In neat (no solvent) at 60℃; for 0.666667h; Friedel-Crafts Alkylation; Green chemistry;85%
benzo-1,4-dioxane
493-09-4

benzo-1,4-dioxane

hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-phenylpropan-1-one
130396-94-0

1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-phenylpropan-1-one

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 30℃; for 1h;84%
With aluminium trichloride In dichloromethane at 15 - 20℃; for 3h;78%

1,4-Benzodioxan Chemical Properties

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

1,4-Benzodioxan Uses

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

1,4-Benzodioxan 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.

1,4-Benzodioxan 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

1,4-Benzodioxan Standards and Recommendations

Purity: 98.0%

1,4-Benzodioxan 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.
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