86-76-0

Basic information

• Product Name: 2-Bromodibenzofuran
• Synonyms: 2-BROMO-DIBENZOFURAN;2-MONOBROMODIBENZOFURAN;2-bromo-dibenzouran;12-broMo-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2,4,6,10,12-hexaene;2-BroModibenzo[b,d]furan;NSC 1735;Dibenzofuran, 2-broMo-
• CAS NO: 86-76-0
• Molecular Formula: C₁₂H₇BrO
• Molecular Weight: 247.09
• EINECS: 1312995-182-4
• Mol File: 86-76-0.mol
• Article Data: 46

Chemical Properties

• Melting Point: 121-122℃
• Boiling Point: 344℃
• Flash Point: 162℃
• Appearance: /Solid
• Density: 1.577
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in hot methanol.
• CAS DataBase Reference: 2-Bromodibenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromodibenzofuran(86-76-0)
• EPA Substance Registry System: 2-Bromodibenzofuran(86-76-0)

Safety Data

• Statements: 22-36-53
• Safety Statements: 26-36-60-61
• Hazardous Substances Data: 86-76-0(Hazardous Substances Data)

Usage

Description

2-Bromo-dibenzofuran is the bromo modified form of dibenzofuran, an aromatic compound consisting two benzene rings fused to a central furan ring. It can be used as a reagent in Friedel-Crafts acylation reactions.

Chemical Properties

off-white powder

Uses

2-Bromodibenzofuran is used as a reagent in Friedel-Crafts acylation reactions.

Synthetic route

2-bromo-6-hydroxy-6H-dibenzo[c,e][1,2]oxaborin → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With 1,10-Phenanthroline; copper diacetate; silver carbonate In ethanol; water at 40℃; for 15h;	95.5%

(x)BF4*C12H8BrN2O(1+) → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With palladium diacetate In ethanol Reflux;	85%

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

Conditions	Yield
With N-Bromosuccinimide; zirconium(IV) chloride In N,N-dimethyl-formamide at 70℃; for 18h; Inert atmosphere; Schlenk technique;	83%
With N-Bromosuccinimide; zirconium(IV) chloride In N,N-dimethyl-formamide at 70℃; for 18h; Schlenk technique; Inert atmosphere;	83%
With bromine In acetic acid Ambient temperature;	82.5%

2-(4-bromo-phenoxy)benzoic acid → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With acethylacetonato(1,5-cyclooctadiene)rhodium(I); potassium iodide In acetic anhydride at 160℃; for 10h; Inert atmosphere;	79%
With 2Ag(1+)*CH2O3(2-); Pd(TFA)2 In 1,4-dioxane; dimethyl sulfoxide at 150℃; for 14h; Inert atmosphere; regioselective reaction;	39%

C12H8BrFO → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With sodium hydroxide In 1-methyl-pyrrolidin-2-one for 3h; Reflux;	75%

dibenzofuran (132-64-9) → 2-bromodibenzo[b,d]furan (86-76-0) + 3,6-dibromo-9-(2-methylpropyl)carbazole (1204702-75-9)

Conditions	Yield
With bromine In water; acetic acid	A 60% B n/a

dibenzofuran (132-64-9) → 2,8-dibromodibenzofuran (10016-52-1) + 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With bromine In chloroform at 20℃; for 240h;	A 47% B n/a

dibenzo[b,d]furan-2-amine (3693-22-9) → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With hydrogenchloride; copper(I) bromide; sodium nitrite

5-bromo-2-phenoxyaniline (56966-45-1) → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With hydrogenchloride; sulfuric acid; sodium nitrite

2-(4-bromo-phenoxy)-aniline (56966-46-2) → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
With hydrogenchloride; sulfuric acid; sodium nitrite

2-hydroxyphenyl boronic acid (89466-08-0) → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride / toluene; ethanol; water / 10 h / 78 °C / Inert atmosphere 2: sodium hydroxide / 1-methyl-pyrrolidin-2-one / 3 h / Reflux View Scheme

1-bromo-4-fluoro-3-iodobenzene (116272-41-4) → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride / toluene; ethanol; water / 10 h / 78 °C / Inert atmosphere 2: sodium hydroxide / 1-methyl-pyrrolidin-2-one / 3 h / Reflux View Scheme

dibenzo[c,e][1,2]oxaborinin-6-ol (14205-96-0) → 2-bromodibenzo[b,d]furan (86-76-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 2 h / 20 °C 2: 1,10-Phenanthroline; silver carbonate; copper diacetate / ethanol; water / 15 h / 40 °C View Scheme

2-bromodibenzo[b,d]furan (86-76-0) + 4,5-dimethyl-9-phenyl-9H-fluoren-9-ol → C33H24O2

Conditions	Yield
With chloro(2’-amino-1,1’-biphenyl-2-yl)palladium(II) dimer; C60H54NO5P; sodium hydride In toluene at 80℃; for 12h; Inert atmosphere; enantioselective reaction;	99%

2-bromodibenzo[b,d]furan (86-76-0) + 2,2-difluoroethenyl 4-methylbenzene-1-sulfonate (185739-14-4) → 2-(2,2-difluorovinyl)dibenzo[b,d]furan

Conditions	Yield
With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl acetamide at 90℃; for 16h;	98%

2-bromodibenzo[b,d]furan (86-76-0) + boric acid tributyl ester (688-74-4) → dibenzofuran-2-ylboronic acid

Conditions	Yield
With triisobutylaluminum In tetrahydrofuran; ethyl acetate at -35 - 24℃; for 0.05h;	96%

2-bromodibenzo[b,d]furan (86-76-0) + C19H16NS(1+)*F6P(1-) → 2-phenyldibenzo[b,d]furan (78210-31-8)

Conditions	Yield
Stage #1: 2-bromodibenzo[b,d]furan With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: C19H16NS(1+)*F6P(1-) In tetrahydrofuran; hexane at -78 - 23℃; for 1.5h; Inert atmosphere;	95%

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-bromodibenzo[b,d]furan (86-76-0) → dibenzofuran-2-ylboronic acid

Conditions	Yield
Stage #1: 2-bromodibenzo[b,d]furan With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 6h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water for 0.5h;	93%
Stage #1: 2-bromodibenzo[b,d]furan With n-butyllithium In tetrahydrofuran; hexane at -40 - 0℃; for 1h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 5h; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexanes for 1h;	72%
Stage #1: 2-bromodibenzo[b,d]furan With n-butyllithium In tetrahydrofuran; hexane at -40 - 0℃; for 1h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran for 1h;	72%

2-bromodibenzo[b,d]furan (86-76-0) + Triisopropyl borate (5419-55-6) → dibenzofuran-2-ylboronic acid

Conditions	Yield
Stage #1: 2-bromodibenzo[b,d]furan With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 6h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane	93%
Stage #1: 2-bromodibenzo[b,d]furan With n-butyllithium In diethyl ether; hexane; toluene at -30 - 0℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -70 - 20℃; for 1h;

2-bromodibenzo[b,d]furan (86-76-0) + N-(4-(3-chloropropoxy)phenyl)dibenzo[b,d]furan-2-amine → N-(4-(3-chloropropoxy)phenyl)-N-(dibenzo[b,d]furan-2-yl)dibenzo[b,d]furan-2-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); Esphos; sodium t-butanolate In toluene at 100℃; for 18h; Inert atmosphere; Schlenk technique;	93%

2-bromodibenzo[b,d]furan (86-76-0) + 4-Aminobiphenyl (92-67-1) → N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-3-amine (1290039-85-8)

Conditions	Yield
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 14h;	92%

4-cyanopyridine N-oxide (14906-59-3) + 2-bromodibenzo[b,d]furan (86-76-0) → dibenzo[b,d]furan-2-carbonitrile (20927-96-2)

Conditions	Yield
With potassium fluoride; 4,4'-dimethyl-2,2'-bipyridines; trifluoroacetic acid; sodium iodide; nickel dichloride; zinc In N,N-dimethyl acetamide at 60℃; for 36h;	92%

2-bromodibenzo[b,d]furan (86-76-0) + 4-Chlorophenylboronic acid (1679-18-1) → C18H11ClO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;	91%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;	91%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Inert atmosphere; Reflux;	83%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 12h; Inert atmosphere; Reflux;	83%

2-bromodibenzo[b,d]furan (86-76-0) + 3-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (1303472-74-3) → C30H19NO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃; for 24h; Inert atmosphere;	90%

2-bromodibenzo[b,d]furan (86-76-0) + C25H17N3 → C37H23N3O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 11h; Inert atmosphere;	90%

2-bromodibenzo[b,d]furan (86-76-0) + (4-(pyridin-3-yl)phenyl)boronic acid → C23H15NO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 78℃; for 10h; Inert atmosphere;	90%

2-bromodibenzo[b,d]furan (86-76-0) + (4-(pyridine-4-yl)phenyl)boronic acid (1045332-30-6) → C23H15NO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 78℃; for 10h; Inert atmosphere;	90%

2-bromodibenzo[b,d]furan (86-76-0) + 2-nitrophenylboronic acid (5570-19-4) → 2-(2-nitrophenyl)dibenzo[b,d]furan (1246308-82-6)

Conditions	Yield
Stage #1: 2-bromodibenzo[b,d]furan; 2-nitrophenylboronic acid With sodium carbonate In ethanol; water; toluene for 1h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 15h; Reflux;	89.6%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 8h; Inert atmosphere; Reflux;	88%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 8h; Inert atmosphere; Reflux;	85%
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 70℃; for 4h;	74%
Stage #1: 2-bromodibenzo[b,d]furan; 2-nitrophenylboronic acid With sodium carbonate In ethanol; water; toluene for 1h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 15h; Reflux;

2-bromodibenzo[b,d]furan (86-76-0) + C9H12BNO4 → C21H17NO3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; toluene for 16h; Inert atmosphere; Reflux;	89.6%

2-bromodibenzo[b,d]furan (86-76-0) + 2-(carbazol-9-yl)-9H-carbazole (1226810-15-6) → 9-(dibenzo[b,d]furan-2-yl)-9H-2,9'-bicarbazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 5h; Inert atmosphere; Reflux;	89%

2-bromodibenzo[b,d]furan (86-76-0) + C36H29NSi → C48H35NOSi

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 80℃; for 6h; Inert atmosphere;	88%

2-bromodibenzo[b,d]furan (86-76-0) + acetonitrile (75-05-8) → dibenzo[b,d]furan-2-carbonitrile (20927-96-2)

Conditions	Yield
With 1,10-Phenanthroline; hexakis(acetonitrile)nickel(II) tetrafluoroborate; 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene at 80℃; for 24h;	88%

2-bromodibenzo[b,d]furan (86-76-0) + 3-Phenylpropenol (104-54-1) → C21H16O

Conditions	Yield
With [2,2]bipyridinyl; manganese; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); zirconium(IV) chloride In N,N-dimethyl acetamide at 20 - 35℃;	87%

2-bromodibenzo[b,d]furan (86-76-0) + C24H16BrNS → C36H22BrNOS

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; Buchwald-Hartwig Coupling;	86%

2-bromodibenzo[b,d]furan (86-76-0) + aniline (62-53-3) → N-(dibenzofuran-2-yl)-N-phenyl-amine (861317-95-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 130℃; for 24h; Inert atmosphere;	86%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 2h; Inert atmosphere; Reflux;	83%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 12h; Inert atmosphere;	80%

2-bromodibenzo[b,d]furan (86-76-0) + C44H35BO2 → C50H30O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Inert atmosphere; Reflux;	86%

2-bromodibenzo[b,d]furan (86-76-0) + benzophenone hydrazone (5350-57-2) → C25H18N2O

Conditions	Yield
With cesium acetate; sodium t-butanolate; XPhos In toluene at 100℃; for 10h; Inert atmosphere;	86%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 12h; Reflux;	64.1%

2-bromodibenzo[b,d]furan (86-76-0) + C12H12BNO2 → C24H17NO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 78℃; for 10h; Inert atmosphere;	86%

2-bromodibenzo[b,d]furan (86-76-0) + C12H12BNO2 → C24H17NO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 78℃; for 10h; Inert atmosphere;	86%

2-bromodibenzo[b,d]furan (86-76-0) + C39H25NO → C51H31NO2

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 125℃; for 8h;	85.5%

Upstream product

• 132-64-9 dibenzofuran 
• 3693-22-9 dibenzo[b,d]furan-2-amine 
• 56966-46-2 2-(4-bromo-phenoxy)-aniline 
• 14205-96-0 dibenzo[c,e][1,2]oxaborinin-6-ol 
• 116272-41-4 4-bromo-1-fluoro-2-iodobenzene 
• 89466-08-0 2-hydroxyphenyl boronic acid 
• 56966-45-1 5-bromo-2-phenoxyaniline 

Downstream Products

• 135892-93-2 2-bromo-8-(phenylacetyl)dibenzofuran 
• 10016-52-1 2,8-dibromodibenzofuran 
• 132-64-9 dibenzofuran 
• 133953-37-4 2-bromo-dibenzofuran-4-carboxylic acid 
• 86-77-1 2-hydroxydibenzofuran 
• 3693-22-9 dibenzo[b,d]furan-2-amine 
• 18919-21-6 dibenzofuran-2-yl-triphenyl-silane 
• 230310-67-5 bis-(2-dibenzofuranyl)-phenylphosphine 
• 230310-66-4 (2-dibenzofuranyl)-diphenylphosphine 
• 135892-94-3 2-bromo-8-(1-hydroxy-2-phenylethyl)dibenzofuran 
• 135892-95-4 [1-(8-Bromo-dibenzofuran-2-yl)-2-phenyl-ethoxy]-tert-butyl-dimethyl-silane 
• 135932-60-4 1-{8-[1-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-dibenzofuran-2-yl}-ethanone 
• 135892-96-5 1-{8-[1-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-dibenzofuran-2-yl}-ethanol 
• 135892-98-7 3-{8-[1-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-dibenzofuran-2-yl}-3-oxo-propionic acid 

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