584-12-3

Basic information

• Product Name: 2-Bromofuran
• Synonyms: BUTTPARK 98\57-03;2-BROMOFURAN;2-Bromofuran96%;2-Bromofurane;2-BROMOETHYLAMINEHYDROBROMIDE;ethyl 5,6-difluoro-1H-indole-2-carboxylate;2-BroMofuran, stabilized with Copper (0.1%), Furan (0.5%) and SodiuM Bicarbonate (0.4%), 95%;2-Bromofuran (stabilized with CaO)
• CAS NO: 584-12-3
• Molecular Formula: C₄H₃BrO
• Molecular Weight: 146.97
• Product Categories: Furan&Benzofuran;Furans, Benzofurans & Dihydrobenzofurans;Halides
• Mol File: 584-12-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 116 °C
• Boiling Point: 52 °C
• Flash Point: 3°C
• Appearance: light yellow liquid
• Density: 1.662
• Vapor Pressure: 32.8mmHg at 25°C
• Refractive Index: 1.4960 to 1.5000
• Sensitive: Light Sensitive
• CAS DataBase Reference: 2-Bromofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromofuran(584-12-3)
• EPA Substance Registry System: 2-Bromofuran(584-12-3)

Safety Data

• Hazard Codes: Xi
• Statements: 11-36/37/38
• Safety Statements: 3/7-9-16-33-37/39-26
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 584-12-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Synthesis Reference(s)

Synthetic Communications, 19, p. 1047, 1989 DOI: 10.1080/00397918908051026

InChI:InChI=1/C4H3BrO/c5-4-2-1-3-6-4/h1-3H

Synthetic route

furan (110-00-9) → 2-bromofuran (584-12-3)

Conditions	Yield
With bromine; ethyllithium In diethyl ether 1.) 25 deg C, 1 h, 2.) -80 deg C;	83%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one for 0.0222222h; microwave irradiation;	78%
With hexabromocyclopenta-1,3-diene In acetonitrile Heating;	75%

5-bromo-furan-2-carboxylic acid (585-70-6) → 2-bromofuran (584-12-3)

Conditions	Yield
With copper In quinoline Heating;	81%
With quinoline; copper at 210℃;	75%
With quinoline; copper
With water; mercury dichloride

furan (110-00-9) → 2-bromofuran (584-12-3) + 2,5-dibromofuran (32460-00-7)

Conditions	Yield
With bromine In N,N-dimethyl-formamide at 30 - 35℃; for 1.5h;	A 72% B 8%
With N-Bromosuccinimide; p-toluenesulfonic acid monohydrate In benzene

furan (110-00-9) + N,N-diethylaniline (91-66-7) → 2-bromofuran (584-12-3)

Conditions	Yield
With bromine In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate	23%

1,4-dioxane (123-91-1) + furan (110-00-9) + bromocyane (506-68-3) → 2-bromofuran (584-12-3) + 2-furancarbonitrile (617-90-3)

furan (110-00-9) + bromocyane (506-68-3) → 2-bromofuran (584-12-3)

Conditions	Yield
With 1,4-dioxane anschliessend Erhitzen mit wss. Natronlauge und Natriumsulfit;

furan (110-00-9) + bromocyane (506-68-3) → 2-bromofuran (584-12-3) + 2-furancarbonitrile (617-90-3)

furan (110-00-9) + bromocyane (506-68-3) → 2-bromofuran (584-12-3) + 2,5-dibromofuran (32460-00-7)

Conditions	Yield
With 1,4-dioxane Erhitzen des Reaktionsgemisches mit wss. Natronlauge und Natriumsulfit;

5-bromo-<2>furylmercury(1+) chloride → 2-bromofuran (584-12-3)

Conditions	Yield
With hydrogenchloride

5-bromo-furan-2-carboxylic acid (585-70-6) + water (7732-18-5) + mercury (II)-chloride → 2-bromofuran (584-12-3)

1-(2-furyl)ethanol (4208-64-4) → 2-bromofuran (584-12-3)

Conditions	Yield
With 1,10-Phenanthroline; oxygen; potassium carbonate In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave; Molecular sieve;	57 %Chromat.

furfural (98-01-1) → 2-bromofuran (584-12-3)

Conditions	Yield
With 1,10-Phenanthroline; oxygen; potassium carbonate In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave; Molecular sieve;	72 %Chromat.

2-bromofuran (584-12-3) + tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → tert-butyl{[3-(2-furyl)prop-2-yn-1-yl]oxy}dimethylsilane

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; Inert atmosphere;	100%

2-bromofuran (584-12-3) + 2-pyrrolidinon (616-45-5) → furazolidone

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine at 110℃; for 24h;	99%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 24h;	82%

2-bromofuran (584-12-3) + 3,4-dimethylphenylmagnesium bromide (89980-68-7) → 2-(3,4-dimethylphenyl)furan (80866-22-4)

Conditions	Yield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether for 16h; Ambient temperature;	98%

2-bromofuran (584-12-3) + thiophen-2-yl magnesium bromide (5713-61-1) → 2-(2-thienyl)furan (27521-80-8)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In diethyl ether 1.) -30 deg C; 2.) RT, 5h;	98%

2-bromofuran (584-12-3) + dimethylsilicon dichloride (75-78-5) → bis (2-furyl)dimethylsilane (1578-44-5)

Conditions	Yield
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 2:1 substrate/Me2SiCl2 ratio, electrochemical conditions (Mg anode, 2.2 F.mol-1);	98%

2-bromofuran (584-12-3) + benzoxazole (273-53-0) → 2-(furan-2-yl)benzoxazole (881-60-7)

Conditions	Yield
With palladium diacetate; sodium t-butanolate; nixantphos In N,N-dimethyl-formamide at 24℃; for 12h; Heck Reaction; Inert atmosphere;	98%
With potassium carbonate In dimethyl sulfoxide at 100℃; for 8h; Green chemistry;	56 %Chromat.

2-bromofuran (584-12-3) + p-ethylphenylmagnesium bromide (22873-28-5) → 2-(4-ethylphenyl)furan (80866-24-6)

Conditions	Yield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether for 16h; Ambient temperature;	97%

2-bromofuran (584-12-3) + 4-methylphenylboronic acid (5720-05-8) → 2-(4-methylphenyl)furan (17113-32-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 75 - 85℃; Suzuki coupling; Inert atmosphere;	97%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 75 - 85℃; Suzuki coupling; Inert atmosphere;	56%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol; water

2-bromofuran (584-12-3) + 4-methoxyphenylboronic acid (5720-07-0) → 2-(4-methoxyphenyl)furan (17113-31-4)

Conditions	Yield
With potassium carbonate In ethanol; water at 20℃; for 16h; Suzuki-Miyaura Coupling;	97%
With potassium carbonate In ethanol; water at 90℃; for 0.5h; Suzuki Coupling; Microwave irradiation;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 75 - 85℃; Suzuki coupling; Inert atmosphere;	77%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 75 - 85℃; Suzuki coupling; Inert atmosphere;	57%

2-bromofuran (584-12-3) + 7-Azaindole (271-63-6) → 1-(furan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
Inert atmosphere;	97%

2-bromofuran (584-12-3) + Dichloromethylvinylsilane (124-70-9) → Methyl-di(2-furyl)vinylsilane (10447-98-0)

Conditions	Yield
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide electrochemical conditions (Mg anode, 2.2 F.mol-1);	96%

2-bromofuran (584-12-3) + 4-bromoisoquinoline (1532-97-4) → 4-(furan-2-yl)isoquinoline

Conditions

Yield

Stage #1: 2-bromofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: 4-bromoisoquinoline With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); XPhos In tetrahydrofuran; hexane at 20℃; for 12h; Negishi Coupling; Inert atmosphere;

96%

2-bromofuran (584-12-3) + isobutylmethyldichlorosilane (18028-96-1) → bis(2-furyl)isobutylmethylsilane

Conditions	Yield
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide electrochemical conditions (Mg anode, 2.2 F.mol-1);	95%

2-bromofuran (584-12-3) + phenylboronic acid (98-80-6) → 2-phenylfuran (17113-33-6)

Conditions	Yield
With potassium carbonate In ethanol; water at 80℃; for 0.333333h; Suzuki-Miyaura Coupling;	95%
With potassium phosphate; tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; palladium dichloride In o-xylene at 90℃; for 24h; Concentration; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	93%
With C30H18Cl2N2O4Pd; tetrabutylammomium bromide; potassium carbonate In ethanol at 60℃; Suzuki-Miyaura Coupling; Sealed tube; Microwave irradiation;	93%

2-bromofuran (584-12-3) + 2-formylthiophene-3-boronic acid (4347-31-3) → 3-(furan-2-yl)thiophene-2-carbaldehyde (1040531-72-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 150℃; for 0.1h; Suzuki coupling; Microwave irradiation;	95%

2-bromofuran (584-12-3) + 1-methyl-5-(pent-4-ynyl)-3,4-dihydropyridin-2(1H)-one (925422-49-7) → 5-(5-(furan-2-yl)pent-4-ynyl)-1-methyl-3,4-dihydropyridin-2(1H)-one (1186722-07-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dichloromethane at 20℃; for 24h; Sonogashira coupling; Inert atmosphere;	95%

2-bromofuran (584-12-3) + m-tolylboronic acid (17933-03-8) → 2-(3-methylphenyl)furan (89929-89-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 75 - 85℃; Suzuki coupling; Inert atmosphere;	95%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 75 - 85℃; Suzuki coupling; Inert atmosphere;	80%

2-bromofuran (584-12-3) + 4-Aminobiphenyl (92-67-1) → C16H13NO

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃;	95%

2-bromofuran (584-12-3) + dichloromethylphenylsilane (149-74-6) → di(2-furyl)(methyl)phenylsilane (217322-06-0)

Conditions	Yield
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 2:1 substrate/PhMeSiCl2 ratio, electrochemical conditions (Mg anode, 2.2 F.mol-1);	94%

2-bromofuran (584-12-3) + 1-ethenyl-4-methylbenzene (622-97-9) → (E)-2-(4-methylphenyl)vinylfuran

Conditions	Yield
With {1,3-bis[2,6-bis(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(pyridine)palladium; caesium carbonate In neat (no solvent) at 100℃; for 12h; Heck Reaction;	93%

2-bromofuran (584-12-3) + tris(4-methoxyphenyl)bismuth (33397-21-6) → 2-(4-methoxyphenyl)furan (17113-31-4)

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 90℃; for 1h;	92%

2-bromofuran (584-12-3) + tert-butylisonitrile (119072-55-8, 7188-38-7) → furan-2-carboxylic acid tert-butylamide (98331-10-3)

Conditions	Yield
With 4,5-dimethyl-1,3-bis-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium chloride; water; nickel dibromide; sodium t-butanolate In toluene at 150℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube;	92%

2-bromofuran (584-12-3) + tris-(4-ethoxy-phenyl)-bismuthine (90591-48-3) → 2-(4-ethoxyphenyl)furan (1407150-38-2)

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 90℃; for 1h;	91%

2-bromofuran (584-12-3) + potassium formate (590-29-4) → 2-furanoic acid (88-14-2)

Conditions	Yield
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;	91%

2-bromofuran (584-12-3) + aniline (62-53-3) → 2-fur-ylaniline

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

2-bromofuran (584-12-3) + 1-(2′-naphthyl)-4,4,4-trifluorobut-2-yn-1-one → C18H10BrF3O

Conditions	Yield
Stage #1: 2-bromofuran; 1-(2′-naphthyl)-4,4,4-trifluorobut-2-yn-1-one In dichloromethane at 20℃; for 6h; Diels-Alder Cycloaddition; Stage #2: With diiron nonacarbonyl In toluene at 80℃; for 2h; regioselective reaction;	89%

2-bromofuran (584-12-3) + chloro-trimethyl-silane (75-77-4) → 2-furyltrimethylsilane (1578-33-2)

Conditions	Yield
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide electrochemical conditions;	88%
Stage #1: 2-bromofuran With n-butyllithium In diethyl ether at 0 - 20℃; for 3.33333h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In diethyl ether at 0℃; Inert atmosphere;	51%

2-bromofuran (584-12-3) + 5-bromo-1H-indole (10075-50-0) → 5-(furan-2-yl)-1H-indole (128373-22-8)

Conditions	Yield
Stage #1: 2-bromofuran With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 5-bromo-1H-indole With potassium phosphate; chloro-(2-dicyclohexylphosphino-2,4,6-triisopropyl-1,1-biphenyl)[2-(2-amino-1,1-biphenyl)]palladium(II) In tetrahydrofuran; hexane; water at 40℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;	88%

2-bromofuran (584-12-3) + 2-bromo-10-H-phenoxazine → C16H10BrNO2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere;	87.2%

2-bromofuran (584-12-3) + dimethylsilicon dichloride (75-78-5) → (2-furyl)dimethylchlorosilane (183118-43-6)

Conditions	Yield
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 1:20 substrate/Me2SiCl2 ratio, electrochemical conditions (Mg anode, 2.2 F.mol-1);	87%
Stage #1: 2-bromofuran With magnesium; ethylene dibromide In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: dimethylsilicon dichloride In tetrahydrofuran; diethyl ether at 20℃; for 20h;

Upstream product

• 98-01-1 furfural 
• 4208-64-4 1-(2-furyl)ethanol 
• 585-70-6 5-bromo-furan-2-carboxylic acid 
• 7732-18-5 water 
• 110-00-9 furan 
• 123-91-1 1,4-dioxane 
• 506-68-3 bromocyane 
• 91-66-7 N,N-diethylaniline 

Downstream Products

• 16191-32-5 2-(2-furanyl)-benzaldehyde 
• 600174-27-4 Pd((C₆H₅)2PC₅H₄)2FeBrC₄H₃O 
• 128373-22-8 5-(furan-2-yl)-1H-indole 
• 856942-97-7 2-fur-ylaniline 
• 1407150-38-2 2-(4-ethoxyphenyl)furan 
• 17113-31-4 2-(4-methoxyphenyl)furan 
• 1911-24-6 2,2'-(methylsilylene)bisfuran 
• 15047-76-4 2<(4-Methoxylphenyl)methyl>furan 
• 1657-55-2 1,2-bis(4-methoxyphenyl)ethane 
• 1071640-07-7 2-(benzyloxy)-1-(furan-2-yl)ethanone 
• 37542-92-0 2-benzylfuran 
• 58861-45-3 2-(4-fluorophenyl)furan 
• 89929-89-5 2-(3-methylphenyl)furan 
• 38527-59-2 2-(2-methoxyphenyl)furan 

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