493-09-4

Basic information

• Product Name: 1,4-Benzodioxan
• Synonyms: 1,2-Ethylenedioxybenzene, 1,4-Benzodioxan, 2,3-Dihydro-1,4-benzodioxin;1,4-Benzodioxan,99%;(R)-1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol;2,3-dihydrobenzo[b][1,4]dioxine 2,3-dihydro-1,4-benzodioxine;2-benzyl-1,4-dioxane;1,4-Benzodioxan, 99% 25ML;2,3-Dihydro-1,4-benzodioxin 1,2-Ethylenedioxybenzene;1,4-Benzodioxane, 1,2-(Ethylenedioxy)benzene
• CAS NO: 493-09-4
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• EINECS: 207-775-6
• Product Categories: Miscellaneous Compounds
• Mol File: 493-09-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: 213-217 °C
• Boiling Point: 103 °C6 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.142 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.039mmHg at 25°C
• Refractive Index: n20/D 1.549(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: insoluble
• BRN: 120846
• CAS DataBase Reference: 1,4-Benzodioxan(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzodioxan(493-09-4)
• EPA Substance Registry System: 1,4-Benzodioxan(493-09-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• WGK Germany: 3
• RTECS: DF4728000
• Hazardous Substances Data: 493-09-4(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO VERY SLIGHTLY YELLOW LIQUID

Uses

Benzo-1,4-dioxane (2,3-dihydro-1,4-benzodioxin) is used in the synthesis of stereoisomers which were evaluated as α- and β- adrenergic antagonists

General Description

The anti-inflammamtory properties and synthesis of carboxylic acid compounds containing benzo-1,4-dioxane (2,3-dihydro-1,4-benzodioxin) subunit was studied.

InChI:InChI=1/C8H8O2/c1-2-4-8-7(3-1)9-5-6-10-8/h1-4H,5-6H2

Synthetic route

2-(2-hydroxy-phenoxy)-ethanol (4792-78-3) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) + ethylene dibromide (106-93-4) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) + benzene-1,2-diol (120-80-9) → benzo-1,4-dioxane (493-09-4) + 2,2'-(1,2-phenylenedioxy)diethanol (10234-40-9)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) + (vinylselenonyl)benzene → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) + 1,2-dibromobenzene (583-53-9) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h;	65%

ethylene glycol (107-21-1) + 1,2-dichloro-benzene (95-50-1) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h;	63%

benzene-1,2-diol (120-80-9) + 1,2-dichloro-ethane (107-06-2) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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

2-fluorophenol (367-12-4) + 2-chloro-ethanol (107-07-3) → benzo-1,4-dioxane (493-09-4) + 2-hydroxyphenyl 2-chloroethyl ether (4792-79-4)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4) + 6-iodo-1,4-benzodioxane (57744-67-9) + 2-(4-iodophenoxy)ethanol (29639-77-8)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4) + 6-iodo-1,4-benzodioxane (57744-67-9)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
(η5-ethyltetramethylcyclopentadienyl)(η6-benzene)rhodium(III) tetrafluoroborate In nitromethane; acetone at 80℃; for 312h;	35%

2-(2-bromo-ethoxy)-phenol (51974-48-2) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
With hydrogenchloride; ethanol

oxirane (75-21-8) + phenylium (17333-73-2) → 1-benzofurane (271-89-6) + 2,3-Dihydrobenzofuran (496-16-2) + benzo-1,4-dioxane (493-09-4) + vinyl phenyl ether (766-94-9)

Conditions	Yield
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) + phenylium (17333-73-2) → 1-benzofurane (271-89-6) + 2,3-Dihydrobenzofuran (496-16-2) + benzo-1,4-dioxane (493-09-4) + phenol (108-95-2)

Conditions	Yield
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) + phenylium (17333-73-2) → 1-benzofurane (271-89-6) + 2,3-Dihydrobenzofuran (496-16-2) + benzo-1,4-dioxane (493-09-4) + vinyl phenyl ether (766-94-9) + phenol (108-95-2)

Conditions	Yield
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) + phenylium (17333-73-2) → 2,3-Dihydrobenzofuran (496-16-2) + benzo-1,4-dioxane (493-09-4) + phenol (108-95-2)

Conditions	Yield
With oxygen under 224 Torr; for 8760h; Ambient temperature; dark;	A 37 % Chromat. B 33 % Chromat. C 30 % Chromat.

ethylene glycol (107-21-1) + cyclohexane-1,2-dione (765-87-7) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride In benzene Heating;	50 % Chromat.

2-fluorophenol (367-12-4) + 2-chloro-ethanol (107-07-3) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) + benzene-1,2-diol (120-80-9) + aqueous alkali → benzo-1,4-dioxane (493-09-4)

1,10-Dimethyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene (110851-22-4) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) + 1,2-bis<2-(-p-toluenesulfonyloxy)ethoxy>amine → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
With sodium iodide In acetone for 2h; Heating / reflux;

2-(2-hydroxy-phenoxy)-ethanol (4792-78-3) + carbonic acid dimethyl ester (616-38-6) → benzo-1,4-dioxane (493-09-4) + C10H12O5

Conditions	Yield
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) → benzo-1,4-dioxane (493-09-4)

Conditions	Yield
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) → 6-bromo-1,4-benzodioxane (52287-51-1)

Conditions	Yield
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) + benzyl alcohol (100-51-6) → 6-Benzyl-2,3-dihydro-benzo[1,4]dioxine

Conditions	Yield
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4;	100%

benzo-1,4-dioxane (493-09-4) + tert-butyl alcohol (75-65-0) → 6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine (93591-46-9)

Conditions	Yield
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4;	100%

benzo-1,4-dioxane (493-09-4) + 2-bromo-5-iodobenzoyl chloride (1261570-98-2) → (2-bromo-5-iodophenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone (1291094-64-8)

Conditions	Yield
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) + benzo-1,4-dioxane (493-09-4) → (2-chloro-5-iodophenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; for 16h;	98.7%

benzo-1,4-dioxane (493-09-4) → 2,3-dihydro-benzo[1,4]dioxin-6-sulfonic acid (127461-51-2)

Conditions	Yield
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) → 2,3-Dihydro-benzo[1,4]dioxine-5,7-disulfonic acid

Conditions	Yield
With sulfur trioxide In nitromethane at 10℃; for 0.25h; other reagent;	98%

benzo-1,4-dioxane (493-09-4) + 5-bromo-2-methylbenzoyl chloride (21900-41-4) → (5-bromo-2-methylphenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone

Conditions	Yield
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) + phenyl isothiocyanate (103-72-0) → 2-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)benzo[d]thiazole (1556673-47-2)

Conditions	Yield
With di-tert-butyl peroxide; copper diacetate In acetonitrile at 120℃; for 6h; Inert atmosphere;	94%

benzo-1,4-dioxane (493-09-4) + chloroethane (75-00-3) → 6-ethylbenzodioxane

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h;	93.1%

benzo-1,4-dioxane (493-09-4) + benzoyl chloride (98-88-4) → 2,3-dihydro-1,4-benzodioxin-6-yl(phenyl)methanone (93637-87-7)

Conditions	Yield
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) + acetyl chloride (75-36-5) → 1,4-benzodioxan-6-yl methyl ketone (2879-20-1)

Conditions	Yield
	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) + tertiary butyl chloride (507-20-0) → 6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine (93591-46-9)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h;	91.2%

benzo-1,4-dioxane (493-09-4) → 6,7-dibromo-2,3-dihydrobenzo[b][1,4]dioxine (25812-80-0)

Conditions	Yield
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) + 4-fluorobenzoyl chloride (403-43-0) → (2,3-Dihydro-benzo[1,4]dioxin-6-yl)-(4-fluoro-phenyl)-methanone (101018-97-7)

Conditions	Yield
With aluminium trichloride In dichloromethane at 15℃; for 1h;	90%

benzo-1,4-dioxane (493-09-4) + 4-chlorobenzoyl chloride (586-75-4) → (4-Bromo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone (101018-99-9)

Conditions	Yield
With aluminium trichloride In dichloromethane at 15℃; for 1h;	90%

benzo-1,4-dioxane (493-09-4) + 1,5-Hexadien (592-42-7) → C20H28O2

Conditions	Yield
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 2h; stereoselective reaction;	90%

benzo-1,4-dioxane (493-09-4) + 3,4,5-Trimethoxybenzoyl chloride (4521-61-3) → 6-(3,4,5-trimethoxybenzoyl)-2,3-dihydro-1,4-benzodioxin (126382-18-1)

Conditions	Yield
With tin(IV) chloride In dichloromethane for 24h; Ambient temperature;	88%

benzo-1,4-dioxane (493-09-4) → 2,3,10,11-tetrahydro[1,4]dioxino[2',3':8,9][1,2,5,6]benzotetrathiocino[3,4-g][1,4]benzodioxine

Conditions	Yield
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) + n-Butyl chloride (109-69-3) → C12H16O2

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h;	87.5%

benzo-1,4-dioxane (493-09-4) → 6-nitro-2,3-dihydrobenzo[b][1,4]dioxine (16498-20-7)

Conditions	Yield
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) + norbornene (498-66-8) → 5,8-bis(bicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1,4-benzodioxine

Conditions	Yield
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) + formaldehyd (50-00-0) → 6,7-bis(bromomethyl)-2,3-dihydrobenzo[b][1,4]dioxine

Conditions	Yield
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) → 6-iodo-1,4-benzodioxane (57744-67-9)

Conditions	Yield
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) + phosphonic acid diethyl ester (762-04-9) → (2,3-dihydro-1,4-benzodioxin-6-yl)phosphonic diethylester

Conditions	Yield
With manganese(III) triacetate dihydrate In acetic acid at 60℃; for 5h;	85%

benzo-1,4-dioxane (493-09-4) + 4-bromo-benzaldehyde (1122-91-4) → C23H19BrO4

Conditions	Yield
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) + hydrocinnamic acid chloride (645-45-4) → 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-phenylpropan-1-one (130396-94-0)

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

Upstream product

• 4792-78-3 2-(2-hydroxy-phenoxy)-ethanol 
• 120-80-9 benzene-1,2-diol 
• 106-93-4 ethylene dibromide 
• 2924-65-4 2-(2-fluorophenoxy)ethan-1-ol 
• 122-99-6 2-Phenoxyethanol 
• 110851-22-4 1,10-Dimethyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.0^3,8]trideca-3,5,7-triene 
• 110851-16-6 2,9,11,12,13-Pentaoxa-tricyclo[8.2.1.0^3,8]trideca-3,5,7-triene 
• 616-38-6 carbonic acid dimethyl ester 
• 95-56-7 2-hydroxybromobenzene 
• 154582-47-5 1-(benzyloxy)-2-(2-bromoethoxy)benzene 
• 51974-48-2 2-(2-bromo-ethoxy)-phenol 
• 3663-82-9 2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin 
• 96-49-1 [1,3]-dioxolan-2-one 
• 52287-51-1 6-bromo-1,4-benzodioxane 

Downstream Products

• 54557-81-2 3-(6-<1,4>benzodioxanylcarbonyl)propionic acid 
• 483-35-2 hystazarin 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 26309-99-9 6-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxine 
• 857373-50-3 1-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-piperidine 
• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 25812-80-0 6,7-dibromo-2,3-dihydrobenzo[b][1,4]dioxine 
• 2879-20-1 1,4-benzodioxan-6-yl methyl ketone 
• 63758-12-3 6-chlorosulfonyl-1,4-benzodioxane 
• 16498-20-7 6-nitro-2,3-dihydrobenzo[b][1,4]dioxine 
• 52287-51-1 6-bromo-1,4-benzodioxane 
• 116939-11-8 monochlormethylbenzo-1,4-dioxane 
• 808-57-1 2,3,6,7,10,11-hexamethoxytriphenylene 
• 134025-10-8 2,3,6,7-tetramethoxy-11,12-dihydrotriphenyleno[2,3-b][1,4]dioxine 

Relevant articles and documents

SYNTHESIS OF BENZO-1,4-DIOXANE IN THE PRESENCE OF INTERPHASE CATALYSTS

Quaternary ammonium salts markedly accelerate the formation of benzo-1,4-dioxane from 1,2-dibromoethane and pyrocatechol under the influence of aqueous alkali and increase its yield.

Ceramic boron carbonitrides for unlocking organic halides with visible light

Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is

Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex

A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.