132-64-9

Basic information

• Product Name: Dibenzofuran
• Synonyms: CPD-926;2, 2-Biphenylylene oxide;Dipheny-oxide;[1,1-Biphenyl]-2,2-diyl oxide;[1,1'-Biphenyl]-2,2'-diyl oxide;2,2-Biphenylene oxide;Dibenzo[b, d]furan;Diphenylene-oxide;Industrial Dibenzofurane;Diphenylene Oxide
• CAS NO: 132-64-9
• Molecular Formula: C₁₂H₈O
• Molecular Weight: 168.19132
• EINECS: 205-071-3
• Mol File: 132-64-9.mol
• Article Data: 228

Chemical Properties

• Melting Point: 81-85℃
• Boiling Point: 287 °C at 760 mmHg
• Flash Point: 135 °C
• Appearance: white to pale yellow crystalline powder
• Density: 1.197 g/cm³
• Vapor Pressure: 0.0044mmHg at 25°C
• Refractive Index: 1.699
• Water Solubility: <0.1 g/100 mL at 20℃
• CAS DataBase Reference: Dibenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzofuran(132-64-9)
• EPA Substance Registry System: Dibenzofuran(132-64-9)

Safety Data

• Hazard Codes: N:Dangerous for the enviro
• Statements: R51/53:
• Safety Statements: S24/25:; S29:; S61:
• Hazardous Substances Data: 132-64-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H

Synthetic route

2'-methoxy-(1,1'-biphenyl)-2-diazonium tetrafluoroborate → dibenzofuran (132-64-9)

Conditions	Yield
In acetonitrile at 20℃; for 15h; Temperature; Time; Inert atmosphere;	100%

1-bromo-2-phenoxybenzene (7025-06-1) → dibenzofuran (132-64-9)

Conditions	Yield
With 6-methoxy quinoline; palladium diacetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 22h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Sealed tube;	99%
With sodium carbonate; palladium diacetate In N,N-dimethyl acetamide at 170℃; for 0.75h;	74%

1-(2-iodophenoxy)benzene (34883-46-0) → dibenzofuran (132-64-9)

Conditions	Yield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate; silver carbonate In N,N-dimethyl acetamide at 130℃;	99%
With palladium 10% on activated carbon; sodium acetate In N,N-dimethyl acetamide at 140℃; for 16h;	95%
With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In N,N-dimethyl acetamide at 130℃; Inert atmosphere;	95%
With potassium acetate; palladium dihydroxide In N,N-dimethyl acetamide at 145℃;	92%
With tricyclohexylphosphine; palladium diacetate In acetonitrile at 100℃; for 24h;

2,2'-dihydroxybiphenyl (1806-29-7) → dibenzofuran (132-64-9)

Conditions	Yield
Nafion-H In o-xylene for 12h; Heating; also with toluene, 36 h;	96%
With phosphorus pentoxide at 300℃;
With zinc(II) chloride at 309.9℃; for 44h; Yield given;
Erhitzen auf Siedetemperatur;
Multi-step reaction with 2 steps 1: Raney nickel; ethanol / 200 °C / 88260.9 Torr / Hydrogenation 2: N-bromo-succinimide; dibenzoyl peroxide; tetrachloromethane View Scheme

2-phenoxyphenyl triflate → dibenzofuran (132-64-9)

Conditions	Yield
With bis(triphenylphosphine)palladium(II)-chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In N,N-dimethyl-formamide at 145℃;	96%

C12H8Cl2Mg2O → dibenzofuran (132-64-9)

Conditions	Yield
With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; lithium chloride In tetrahydrofuran	96%

dibenzofuran-4-carbaldehyde (96706-46-6) → dibenzofuran (132-64-9)

Conditions	Yield
With palladium diacetate; potassium carbonate In ethyl acetate at 150℃; under 12929 Torr; for 0.833333h; Microwave irradiation; Molecular sieve;	96%
With palladium diacetate In cyclohexane at 140℃; for 24h; Molecular sieve; air;	89%
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 20 °C 2: sodium carbonate; palladium diacetate; oxygen / 36 h / 130 °C / Molecular sieve; Schlenk technique View Scheme

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate (189999-35-7) → dibenzofuran (132-64-9)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In water at 100℃; for 24h;	96%
With water; copper diacetate; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;	88%

dibenzo[c,e][1,2]oxaborinin-6-ol (14205-96-0) → dibenzofuran (132-64-9)

Conditions	Yield
With 1,10-Phenanthroline; copper diacetate; silver carbonate In ethanol; water at 40℃; for 19h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time;	94.5%

2-bromodibenzo[b,d]furan (86-76-0) → dibenzofuran (132-64-9)

Conditions	Yield
With sodium hydroxide In isopropyl alcohol at 20℃; for 1h; UV-irradiation;	94%
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 4h; Electrolysis; Green chemistry;	94%
Stage #1: 2-bromodibenzo[b,d]furan With nickel(II) iodide; 1,4-bis(dicyclohexylphosphino)butane; sodium carbonate; cesium iodide In tetrahydrofuran for 0.25h; Schlenk technique; Glovebox; Stage #2: In tetrahydrofuran at 35℃; for 72h; Irradiation;	90%

2,3-dihydrodibenzofuran → dibenzofuran (132-64-9)

Conditions	Yield
In toluene at 95℃; for 12h; Sealed tube;	94%

2,2'-difluorobiphenyl (388-82-9) → dibenzofuran (132-64-9)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium tert-butylate at 120℃; for 3h; Reagent/catalyst; Microwave irradiation;	93%
With aluminum oxide In neat (no solvent) at 190℃; for 12h;

phenoxathiine (262-20-4) → dibenzofuran (132-64-9) + diphenylether (101-84-8)

Conditions	Yield
With lithium aluminium tetrahydride; (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel In tetrahydrofuran at 55℃; for 48h;	A 3% B 92%
With 3-Hydroxy-1-methylpiperidine; nickel diacetate; sodium hydride In tetrahydrofuran at 65℃; for 0.5h;	A 2% B 81%
With lithium aluminium tetrahydride; (2,2'-bipyridyl)(1,5-cyclooctadiene)nickel In tetrahydrofuran at 55℃; for 48h;	A 79% B 3%

2′-chloro-[1,1′-biphenyl]-2-ol (53824-24-1) → dibenzofuran (132-64-9)

Conditions	Yield
With sodium t-butanolate; di-tert-butyl (2'-methyl-[1,1'-biphenyl]-2-yl)phosphine; palladium diacetate In toluene at 100℃; for 24h;	92%
With copper(I) thiophene-2-carboxylate In N,N-dimethyl acetamide at 140℃; for 0.333333h; microwave irradiation;	89%
With potassium tert-butylate In dimethyl sulfoxide at -33℃; for 3h; Reagent/catalyst; Schlenk technique; Inert atmosphere; UV-irradiation;	89%

4-bromodibenzofuran (89827-45-2) → dibenzofuran (132-64-9)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 15h; Irradiation; Inert atmosphere;	92%

2-phenoxybenzoic acid (2243-42-7) → dibenzofuran (132-64-9)

Conditions	Yield
With acethylacetonato(1,5-cyclooctadiene)rhodium(I); potassium iodide In acetic anhydride at 160℃; for 10h; Reagent/catalyst; Inert atmosphere;	91%
With 2Ag(1+)*CH2O3(2-); Pd(TFA)2 In 1,4-dioxane; dimethyl sulfoxide at 150℃; for 14h; Reactivity; Reagent/catalyst; Solvent; Inert atmosphere;	85%
Multi-step reaction with 2 steps 1: 12 h / 20 °C / Inert atmosphere 2: acethylacetonato(1,5-cyclooctadiene)rhodium(I); potassium iodide / acetic anhydride / 10 h / 160 °C / Inert atmosphere View Scheme
With copper(I) oxide; potassium carbonate In water at 80℃; for 2h; Catalytic behavior; Reagent/catalyst; Sonication; Green chemistry; chemoselective reaction;

10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine (19014-28-9) → dibenzofuran (132-64-9)

Conditions	Yield
With iodine; palladium diacetate; potassium carbonate In acetonitrile at 20 - 80℃; for 12h; Suzuki Coupling; Schlenk technique; Inert atmosphere; Sealed tube;	90%

4-dibenzofurylboronic acid (100124-06-9) → dibenzofuran (132-64-9)

Conditions	Yield
With sodium hypochlorite; tetrabutylammomium bromide; water at 100℃;	90%

2-phenoxybenzenediazonium tetrafluoroborate → dibenzofuran (132-64-9)

Conditions	Yield
With palladium diacetate In ethanol Reflux;	89%

3-dibenzofurandiazonium tetrafluoroborate → dibenzofuran (132-64-9)

Conditions	Yield
With chloro-trimethyl-silane In tetrahydrofuran; N,N-dimethyl-formamide at 60℃; for 1h;	88%

2-phenoxyphenyltosylate (1285625-78-6) → dibenzofuran (132-64-9)

Conditions	Yield
With palladium diacetate; caesium carbonate; cesium pivalate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 120℃; for 17h; Reagent/catalyst; Glovebox; Sealed tube;	88%

acetic 2-phenoxybenzoic anhydride (1434906-71-4) → dibenzofuran (132-64-9)

Conditions	Yield
With acethylacetonato(1,5-cyclooctadiene)rhodium(I); potassium iodide In acetic anhydride at 160℃; for 10h; Inert atmosphere;	88%

dimethyl sulfoxide (67-68-5) + 2'-methoxy-(1,1'-biphenyl)-2-diazonium tetrafluoroborate → dibenzofuran (132-64-9) + O-methyldimethylsulfoxonium fluoroborate

Conditions	Yield
In dichloromethane	A 87% B 79%

cyclopentadienyliron hexafluorophosphate of dibenzofuran → dibenzofuran (132-64-9)

Conditions	Yield
In N,N-dimethyl-formamide electrolysis in 0.2M KClO4 with mercury pool working electrode, Ag/0.1M AgNO3 reference electrode, Pt counter electrode, potential -1.80 V;	87%

toluene-4-sulfonic acid dibenzofuran-2-yl ester → dibenzofuran (132-64-9)

Conditions	Yield
With sodium tetrahydroborate; bis(triphenylphosphine)nickel(II) chloride; tricyclohexylphosphine In tetrahydrofuran at 20℃; for 14h;	87%

2-Phenoxy-1-(trimethylsilyl)benzol (17049-42-2) → dibenzofuran (132-64-9)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; (R)-10-camphorsulfonic acid; tetrahydrothiophene gold(III) bromide In methanol; chloroform at 27℃; for 0.5h; Schlenk technique; Inert atmosphere;	87%

2-chlorodiphenyl ether (2689-07-8) → dibenzofuran (132-64-9)

Conditions	Yield
With potassium carbonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; N-heterocyclic carbene palladium In N,N-dimethyl acetamide at 130℃;	86%

3-bromoquinoline (5332-24-1) + 4-dibenzofurylboronic acid (100124-06-9) → dibenzofuran (132-64-9) + 3-(4-dibenzofuranyl)quinoline (1004751-41-0) + 4,4'-bidibenzo[b,d]furan (86532-14-1)

Conditions	Yield
With sodium phosphate dodecahydrate; palladium 10% on activated carbon In water; isopropyl alcohol at 80℃; for 24h; hetero-Suzuki-Miyaura cross-coupling; Inert atmosphere;	A 86% B 5% C 4%

C14H11BrO2 → dibenzofuran (132-64-9)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 130℃; for 12h;	86%

n-butyllithium (109-72-8, 29786-93-4) + dibenzofuran (132-64-9) + dimethyl sulfate (77-78-1) → 4-methyl-dibenzofuran (7320-53-8)

Conditions	Yield
In tetrahydrofuran; hexane	100%

dibenzofuran (132-64-9) → dibenzofuran-d8

Conditions	Yield
With water-d2; isopropyl alcohol In n-heptane at 120℃; Flow reactor;	99%
With platinum(IV) oxide; (+/-)-2-pentanol; water-d2 In decalin at 100℃; for 12h; High pressure;	72%

dibenzofuran (132-64-9) → 2-nitrodibenzofuran (20927-95-1)

Conditions	Yield
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 2h; Ionic liquid;	96%
With nitric acid; acetic acid at 60℃; for 3h;	78%
With nitric acid; acetic anhydride
With nitric acid; acetic acid

dibenzofuran (132-64-9) + carbon dioxide (124-38-9) → 4,6-dibenzofuran dicarboxylic acid (88818-47-7)

Conditions	Yield
Stage #1: dibenzofuran With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; cyclohexane at -78 - 25℃; for 25h; Inert atmosphere; Stage #2: carbon dioxide In diethyl ether; cyclohexane at -78 - 25℃; for 5h; Inert atmosphere;	96%
Stage #1: dibenzofuran With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; cyclohexane at 25℃; for 18h; Stage #2: carbon dioxide In diethyl ether; cyclohexane at -78 - 20℃; for 19h; Stage #3: With hydrogenchloride; water In diethyl ether; cyclohexane	76%
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether at 25℃;	30%

dibenzofuran (132-64-9) → dibenzofuran 2,8-disulfonyl chloride (47146-53-2)

Conditions	Yield
With chlorosulfonic acid; potassium chloride at 50 - 70℃; for 3h;	96%
With chlorosulfonic acid; thionyl chloride for 3h; Heating;	89%

dibenzofuran (132-64-9) + 11H-Benzo[b]fluoren-11-one (3074-03-1) → C29H18O2

Conditions	Yield
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 11H-Benzo[b]fluoren-11-one In tetrahydrofuran at -78 - 20℃;	96%

dibenzofuran (132-64-9) + acetyl chloride (75-36-5) → 2-acetyldibenzofuran (13761-32-5)

Conditions	Yield
With aluminum (III) chloride In chloroform at 20℃; for 0.75h; Friedel Crafts acylation;	95%
With aluminum (III) chloride In chloroform at 20℃; for 0.75h;	95%
With aluminum (III) chloride In chloroform at 0 - 20℃; Friedel-Crafts Acylation;	95%

dibenzofuran (132-64-9) + succinic acid monomethylester chloride (1490-25-1) → γ-oxo-2-dibenzofuranbutanoic acid methyl ester (36109-81-6)

Conditions	Yield
With aluminium trichloride In 1,1,2,2-tetrachloroethane at 0 - 20℃; for 3h; Friedel-Crafts reaction;	94%

dibenzofuran (132-64-9) + Trimethyl borate (121-43-7) + water (7732-18-5) → 4-dibenzofurylboronic acid (100124-06-9)

Conditions	Yield
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran; hexane; acetone at -60 - 20℃; for 5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane; acetone at -45 - 20℃; for 15h; Inert atmosphere; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane; acetone at 10 - 20℃; for 4h; Inert atmosphere;	93.8%
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 12.5h; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane at 0℃;	69.3%

dibenzofuran (132-64-9) → 3,3'-Diiododiphenylene oxide (137959-93-4)

Conditions	Yield
Stage #1: dibenzofuran With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; cyclohexane at -78 - 20℃; Inert atmosphere; Stage #2: With iodine In diethyl ether; cyclohexane at -78 - 20℃; Inert atmosphere;	93%
Stage #1: dibenzofuran With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere;	79%
Stage #1: dibenzofuran With n-butyllithium In diethyl ether at -78 - 20℃; for 10h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; diethyl ether at -78 - 20℃; for 4h; Inert atmosphere;	67%

2-Adamantanone (700-58-3) + dibenzofuran (132-64-9) → 2-(2-hydroxyadamantan-2-yl)-2'-hydroxybiphenyl

Conditions	Yield
Stage #1: dibenzofuran With N,N,N,N,-tetramethylethylenediamine; lithium In diethyl ether for 24h; Heating; Stage #2: 2-Adamantanone In diethyl ether at -78 - 20℃;	93%

dibenzofuran (132-64-9) + (-)-(o-menthyl)chlorophenylphosphine → ((-)-mentholate)(dbf)PhP(BH3)

Conditions	Yield
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: (-)-(o-menthyl)chlorophenylphosphine In tetrahydrofuran; hexane at -78 - 20℃; for 10h; Inert atmosphere; Stage #3: With borane-THF In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere;	93%

dibenzofuran (132-64-9) + Triisopropyl borate (5419-55-6) → B,B'-4,6-dibenzofurandiylbisboronic acid (145238-17-1)

Conditions	Yield
Stage #1: dibenzofuran With sec.-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 6h;	93%

dibenzofuran (132-64-9) → 2-Phenylphenol (90-43-7)

Conditions	Yield
With sodium hydride at 190 - 192℃; for 7h;	92.5%
With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;	84%
With lithium aluminium tetrahydride; cobalt acetylacetonate; sodium t-butanolate In toluene at 140℃; for 24h; Inert atmosphere; Sealed tube;	81%

dibenzofuran (132-64-9) + carbon dioxide (124-38-9) → Dibenzofuran-1-carboxylic acid (54470-37-0)

Conditions	Yield
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran; hexane at -75 - 20℃; for 3.08333h; Stage #2: carbon dioxide In tetrahydrofuran; diethyl ether; hexane at -74℃; for 1h; Stage #3: With hydrogenchloride In water pH=2;	92%

Upstream product

• 13264-84-1 myo-Inositol, 1,2,4,5,6-pentakis-O-(phenylmethyl)- 
• 132647-09-7 Fatty acids, coco, reaction products with 2-(2-aminoethyl)aminoethanol, bis(2-carboxyethyl) derivs., disodium salts 
• 132647-08-6 SODIUM COCOAMPHOPROPIONATE 
• 132646-18-5 5-isopropenyl-2-methyl-1-(N-(2-phenylcyclohexyloxycarbonyl)amino)-2-cyclohexene 
• 132646-01-6 2-(hydroxy(phenyl)methyl)-2-methylcyclohexanone 
• 132645-97-7 dynemicin S 
• 132644-88-3 (METHYLCYCLOPENTADIENYL)(1,5-CYCLOOCTADIENE)IRIDIUM(I) 
• 132644-83-8 Pyridine, 1-acetyl-1,2,3,6-tetrahydro-2,2-dimethyl- (9CI) 
• 13264-41-0 ETHYLHEXADECYLDIMETHYLAMMONIUMCHLORIDE 
• 132643-73-3 3H-Pyrazolo[4,3-b]pyridin-3-amine(9CI) 
• 132643-66-4 Oxepino[3,2-c]pyridine (9CI) 
• 132643-65-3 Oxepino[2,3-c]pyridine (9CI) 
• 132642-25-2 Pt-bis-netropsin 
• 13264-13-6 N~2~,N~2~,N~4~,N~4~,N~6~,N~6~-hexaphenyl-1,3,5,2lambda~5~,4lambda~5~,6lambda~5~-triazatriphosphinine-2,2,4,4,6,6-hexamine 

Downstream Products

• 10331-57-4 NICLOFOLAN 

Recommend Products

• 38873-55-1  furobufen 
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• 77358-96-4  2-chloromethyldibenzofuran 
• 50-00-0  formaldehyd 
• 5397-82-0  dibenzofuran-2-carbaldehyde 
• 74-90-8  hydrogen cyanide 
• 56260-30-1  dibenzofuran-2-yl-o-tolyl-methanone 
• 95-49-8  2-methylchlorobenzene 
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