Product Name

  • Name

    Benzofuran

  • EINECS 205-982-6
  • CAS No. 271-89-6
  • Article Data161
  • CAS DataBase
  • Density 1.11 g/cm3
  • Solubility Insoluble in water
  • Melting Point <-18 °C
  • Formula C8H6O
  • Boiling Point 174 °C at 760 mmHg
  • Molecular Weight 118.135
  • Flash Point 56.1 °C
  • Transport Information UN 1993 3/PG 3
  • Appearance Colorless to light yellow liquid
  • Safety 36/37-16
  • Risk Codes 40-52-10
  • Molecular Structure Molecular Structure of 271-89-6 (Benzofuran)
  • Hazard Symbols IrritantXi, HarmfulXn
  • Synonyms 1-Oxidene;1-Oxindene;2,3-Benzofuran;Coumarone;
  • PSA 13.14000
  • LogP 2.43280

Synthetic route

1-(1-propenyl)-2-vinyloxybenzene

1-(1-propenyl)-2-vinyloxybenzene

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With Grubbs catalyst first generation In dichloromethane at 20℃; for 8h;100%
2-bromo-1-benzofuran
54008-77-4

2-bromo-1-benzofuran

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 0.7h; Inert atmosphere;89%
(2,2-diethoxy-ethoxy)-benzene
32438-31-6

(2,2-diethoxy-ethoxy)-benzene

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With polyphosphoric acid In 1,2-dichloro-ethane for 4h; Reflux;83.9%
With tin-exchanged H-b zeolite (Sn-b) for 0.5h; Reagent/catalyst; Time; Reflux;78%
With oxalic acid
With polyphosphoric acid In toluene for 12h; Reflux;
With polyphosphoric acid In toluene for 12h; Reflux;
Benzofuran-2-carboxylic acid
496-41-3

Benzofuran-2-carboxylic acid

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With 1,10-Phenanthroline; copper hydroxide In 1-methyl-pyrrolidin-2-one at 190℃; for 4h; Inert atmosphere; Green chemistry;82%
at 140℃; for 4h; Ionic liquid;71%
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] In toluene at 120℃; for 16h;67%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

tert-butylethylene
558-37-2

tert-butylethylene

A

1-benzofurane
271-89-6

1-benzofurane

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With (PSCOP)IrHCl; sodium t-butanolate In para-xylene at 120℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A 80%
B n/a
2,3-dihydro-2-ethoxybenzofuran

2,3-dihydro-2-ethoxybenzofuran

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 0.5h; Heating;76%
nitromethane
75-52-5

nitromethane

salicylaldehyde
90-02-8

salicylaldehyde

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
at 75 - 80℃; for 4h; Temperature; Reagent/catalyst;74.5%
With sodium hydrogen sulfite; silica gel at 75 - 80℃; for 4h; Temperature;74.5%
β-(2-hydroxyphenyl)nitroethane
96853-36-0

β-(2-hydroxyphenyl)nitroethane

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
Stage #1: β-(2-hydroxyphenyl)nitroethane With sodium hydroxide at 20℃; for 0.5h; Nef reaction;
Stage #2: With sulfuric acid at 0 - 20℃; Nef Reaction;
74%
Stage #1: β-(2-hydroxyphenyl)nitroethane With sodium hydroxide In water at 20℃; for 0.25h;
Stage #2: With sulfuric acid at 0℃; for 0.5h;
68%
(E)-3-(2-Allyloxy-phenyl)-acrylic acid methyl ester
152842-85-8

(E)-3-(2-Allyloxy-phenyl)-acrylic acid methyl ester

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
at 650℃; under 0.001 - 0.01 Torr;68%
methyl (E)-3-(2-(allyloxy)phenyl)acrylate

methyl (E)-3-(2-(allyloxy)phenyl)acrylate

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
at 650℃; under 0.01 Torr; for 0.25h;68%
(-/+)-3-hydroxy-2,3-dihydrobenzofuran
5380-80-3

(-/+)-3-hydroxy-2,3-dihydrobenzofuran

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With potassium hydrogensulfate67%
With perchloric acid In water at 25℃; Rate constant; Mechanism;
1-(dichloromethyl)-2-methoxybenzene
17647-57-3

1-(dichloromethyl)-2-methoxybenzene

A

1-benzofurane
271-89-6

1-benzofurane

B

benzyl chloride
100-44-7

benzyl chloride

Conditions
ConditionsYield
at 600℃; under 0.1 Torr; flash vacuum pyrolysis;A 65%
B 3%
3-bromobenzofuran
59214-70-9

3-bromobenzofuran

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Time; Inert atmosphere;64%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 22h; Reagent/catalyst; Inert atmosphere;64%
2-<2-hydroxy-1-(isopropylthio)ethyl>phenol
121045-14-5

2-<2-hydroxy-1-(isopropylthio)ethyl>phenol

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With hydrogenchloride In 2-methoxy-ethanol for 4h; Heating;61%
2-nitrofuran
609-39-2

2-nitrofuran

1-(N-acetyl-N-propylamino)-1,3-butadiene

1-(N-acetyl-N-propylamino)-1,3-butadiene

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
In benzene at 120℃; for 72h; Diels-Alder reaction;58%
2-(phenylsulfinyl)benzofuran

2-(phenylsulfinyl)benzofuran

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With 2-(trimethylsilyl)phenyl trifluoromethanesulfonate; cesium fluoride In acetonitrile at 20℃; for 12h; Inert atmosphere; Glovebox;58%
2-(phenylsulfinyl)benzofuran

2-(phenylsulfinyl)benzofuran

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 20℃; for 12h; Inert atmosphere;58%
(2-ethynylphenoxy)triisopropylsilane
199010-94-1

(2-ethynylphenoxy)triisopropylsilane

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With 4 A molecular sieve; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃;56%
dibromobenzofuran
64150-61-4

dibromobenzofuran

A

1-benzofurane
271-89-6

1-benzofurane

B

3-bromobenzofuran
59214-70-9

3-bromobenzofuran

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 23℃; for 0.7h; Reagent/catalyst; Inert atmosphere; regioselective reaction;A 31%
B 56%
2-Allyloxystilbene

2-Allyloxystilbene

A

1-benzofurane
271-89-6

1-benzofurane

B

2-phenylbenzofuran
1839-72-1

2-phenylbenzofuran

C

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
at 650℃; under 0.001 Torr; for 1.5h;A n/a
B 55%
C n/a
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With sodium anthraquinone-2-sulfonate; oxygen; palladium diacetate; magnesium sulfate; toluene-4-sulfonic acid In chlorobenzene at 110℃; under 760.051 Torr; for 24h;53%
With copper(I) oxide; dmap; N-hydroxyphthalimide; oxygen In acetonitrile at 120℃; for 12h; Sealed tube;45%
With [2,2]bipyridinyl; iron(III) chloride; di-tert-butyl peroxide In toluene at 135℃; for 14h; Reagent/catalyst;31%
2-Formylphenoxyacetic acid
6280-80-4

2-Formylphenoxyacetic acid

A

1-benzofurane
271-89-6

1-benzofurane

B

Benzofuran-2-carboxylic acid
496-41-3

Benzofuran-2-carboxylic acid

Conditions
ConditionsYield
With sodium acetate; acetic anhydride at 110℃; for 3h;A 22.2%
B 53%
With sodium acetate; acetic anhydride at 110℃; for 3h;A 22.2%
B 53%
1-(furan-2-yl)but-3-yn-2-ol

1-(furan-2-yl)but-3-yn-2-ol

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold (I) In dichloromethane at 20℃; for 2h;53%
benzofuran-2-carbonyl fluoride

benzofuran-2-carbonyl fluoride

A

1-benzofurane
271-89-6

1-benzofurane

B

2-formylbenzo[b]furan
4265-16-1

2-formylbenzo[b]furan

Conditions
ConditionsYield
With triethylsilane; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;A 8 %Chromat.
B 50%
coumarin
91-64-5

coumarin

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With quinoline; copper; sodium hydroxide at 190℃;39%
at 860℃; durch ein verzinntes Eisenrohr;
With nickel at 350℃;
2-(β,β-dibromovinyl)phenol
91703-34-3

2-(β,β-dibromovinyl)phenol

A

1-benzofurane
271-89-6

1-benzofurane

B

2-ethynyl-phenol
5101-44-0

2-ethynyl-phenol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -70℃; for 2h;A 35%
B 38%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

tert-butylethylene
558-37-2

tert-butylethylene

A

1-benzofurane
271-89-6

1-benzofurane

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

C

2,2'-bibenzofuranyl
41014-29-3

2,2'-bibenzofuranyl

Conditions
ConditionsYield
With (PSCOP)IrHCl; sodium t-butanolate In para-xylene at 120℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A 11%
B n/a
C 37%
lead(IV) acetate

lead(IV) acetate

tributyl(o-methoxystyryl)stannane
682356-47-4, 202598-29-6, 105445-61-2

tributyl(o-methoxystyryl)stannane

A

1-benzofurane
271-89-6

1-benzofurane

B

(E)-o-methoxystyryl-lead triacetate
174535-20-7, 131428-32-5

(E)-o-methoxystyryl-lead triacetate

C

(Z)-o-methoxystyryl-lead triacetate
174535-20-7, 131428-32-5

(Z)-o-methoxystyryl-lead triacetate

Conditions
ConditionsYield
In chloroform-d1 room temp., 2 min; not isolated; (1)H-NMR monitoring;A 35%
B n/a
C n/a
(1α,2α,4α,5α,6α,8α)-3-Oxatetracyclo<3.3.1.02,4.06,8>nonan-9-one
85267-53-4

(1α,2α,4α,5α,6α,8α)-3-Oxatetracyclo<3.3.1.02,4.06,8>nonan-9-one

1-benzofurane
271-89-6

1-benzofurane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 80℃; for 3h; Mechanism;33%
1-benzofurane
271-89-6

1-benzofurane

2-iodobenzofuran
69626-75-1

2-iodobenzofuran

Conditions
ConditionsYield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 1h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran at 20℃; Inert atmosphere;
100%
Stage #1: 1-benzofurane With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #2: With iodine In tetrahydrofuran for 16h;
99%
Stage #1: 1-benzofurane In tetrahydrofuran; diethyl ether; hexane at -78℃; for 3h;
Stage #2: With iodine In tetrahydrofuran; diethyl ether; hexane at 20℃; for 16h; Further stages.;
95%
1-benzofurane
271-89-6

1-benzofurane

3,5-Dichloroaniline
626-43-7

3,5-Dichloroaniline

Glyoxilic acid
298-12-4

Glyoxilic acid

1,3-dichloro-5,6,6a,11b-tetrahydro-7-oxa-5-aza-benzo[c]fluorene-6-carboxylic acid

1,3-dichloro-5,6,6a,11b-tetrahydro-7-oxa-5-aza-benzo[c]fluorene-6-carboxylic acid

Conditions
ConditionsYield
indium(III) triflate In acetonitrile at 50℃; for 0.191667h; Product distribution / selectivity; Microwave irradiation;100%
montmorillonit KSF In acetonitrile at 50℃; for 0.191667h; Product distribution / selectivity; Microwave irradiation;79%
ytterbium(III) triflate In acetonitrile at 50℃; for 0.191667h; Product distribution / selectivity; Microwave irradiation;77%
1-benzofurane
271-89-6

1-benzofurane

1-bromo dodecane
112-29-8

1-bromo dodecane

2-decylbenzo[b]furan
151491-46-2

2-decylbenzo[b]furan

Conditions
ConditionsYield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: 1-bromo dodecane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
100%
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: 1-bromo dodecane In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;
30%
1-benzofurane
271-89-6

1-benzofurane

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With methanol; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;99%
With hydrogen In methanol at 80 - 90℃; under 750.075 - 22502.3 Torr; Reagent/catalyst; Autoclave;97.8%
With ethanol; (BQ‑NCOP)IrHCl; sodium t-butanolate at 60℃; for 5h; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;96%
1-benzofurane
271-89-6

1-benzofurane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan
402503-13-3

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan

Conditions
ConditionsYield
With 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In hexane at 25℃; for 1h;99%
With (iPrPNP)CoCH2SiMe3 In neat (no solvent) at 23℃; for 0.25h; Reagent/catalyst; Temperature; Inert atmosphere; Glovebox;99%
With (iPrPNP)CoCH2SiMe3 In neat (no solvent) at 23℃; for 0.25h; Reagent/catalyst;99%
1-benzofurane
271-89-6

1-benzofurane

methanol
67-56-1

methanol

tetrachloromethane
56-23-5

tetrachloromethane

methyl benzofuran-2-carboxylate
1646-27-1

methyl benzofuran-2-carboxylate

Conditions
ConditionsYield
With iron(II) bromide at 160℃; for 4h; Inert atmosphere; sealed ampule; regioselective reaction;99%
1-benzofurane
271-89-6

1-benzofurane

butyl isothiocyanate
592-82-5

butyl isothiocyanate

N-(n-butyl)benzofuran-2-carbothioamide
1258217-03-6

N-(n-butyl)benzofuran-2-carbothioamide

Conditions
ConditionsYield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: butyl isothiocyanate In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere;
99%
1-benzofurane
271-89-6

1-benzofurane

formic acid ethyl ester
109-94-4

formic acid ethyl ester

ethyl coumarilate
3199-61-9

ethyl coumarilate

Conditions
ConditionsYield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h;
Stage #2: formic acid ethyl ester In tetrahydrofuran; hexane at -78℃; for 3h;
Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 13h;
99%
1-benzofurane
271-89-6

1-benzofurane

diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

2-phenylbenzofuran
1839-72-1

2-phenylbenzofuran

Conditions
ConditionsYield
With impregnated palladium on magnetite catalyst PdO-Fe3O4 (10 mol percent Pd) In ethanol at 60℃; for 24h; regioselective reaction;99%
With 5%-palladium/activated carbon In ethanol at 60℃; for 22h; regioselective reaction;77%
With palladium In tetrahydrofuran at 60℃; for 24h;77%
With palladium diacetate In ethanol at 60℃; for 24h; Kinetics; Reagent/catalyst;31%
1-benzofurane
271-89-6

1-benzofurane

2-deuteriobenzofuran
27124-07-8

2-deuteriobenzofuran

Conditions
ConditionsYield
Stage #1: 1-benzofurane With n-butyllithium In diethyl ether; hexane at -20℃; for 1h;
Stage #2: With water-d2 In diethyl ether; hexane at -20 - 23℃;
99%
Stage #1: 1-benzofurane With n-butyllithium In diethyl ether at -20℃; for 1h;
Stage #2: With water-d2 In diethyl ether at -20 - 23℃;
1-benzofurane
271-89-6

1-benzofurane

C13H14BNO5

C13H14BNO5

2-(p-acetylphenyl)benzofuran
132932-61-7

2-(p-acetylphenyl)benzofuran

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; C24H36N2O2Pd*2C2H4O2; cesium trifluoroacetate; trifluoroacetic acid; p-benzoquinone; silver(l) oxide In water at 30℃; for 20h; regioselective reaction;99%
1-benzofurane
271-89-6

1-benzofurane

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

2-(4-fluorophenyl)benzoxazole
397-54-6

2-(4-fluorophenyl)benzoxazole

Conditions
ConditionsYield
With C13H18Cl2N4OPd; lithium tert-butoxide In N,N-dimethyl-formamide at 130℃; for 24h; Catalytic behavior; Inert atmosphere; Schlenk technique;99%
1-benzofurane
271-89-6

1-benzofurane

6-phenylspiro[2.5]oct-1-ene
1619992-33-4

6-phenylspiro[2.5]oct-1-ene

1-((4-phenylcyclohexylidene)methyl)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran

1-((4-phenylcyclohexylidene)methyl)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran

Conditions
ConditionsYield
With dirhodium tetraacetate In dichloromethane at 20℃; for 21h; Inert atmosphere; Sealed tube; diastereoselective reaction;99%
1-benzofurane
271-89-6

1-benzofurane

7,10-dioxadispiro[2.2.46.23]dodec-1-ene

7,10-dioxadispiro[2.2.46.23]dodec-1-ene

1-((1,4-dioxaspiro[4.5]decan-8-ylidene)methyl)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran

1-((1,4-dioxaspiro[4.5]decan-8-ylidene)methyl)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran

Conditions
ConditionsYield
With dirhodium tetraacetate In dichloromethane at 20℃; for 21h; Inert atmosphere; Sealed tube; diastereoselective reaction;99%
1-benzofurane
271-89-6

1-benzofurane

3-bromo-1-[(diphenylmethylene)amino]-2-piperidinone
93623-88-2

3-bromo-1-[(diphenylmethylene)amino]-2-piperidinone

2-benzofuranyl-[[1-(diphenylmethylene)amino]-2-pyrrolidinyl]methanone

2-benzofuranyl-[[1-(diphenylmethylene)amino]-2-pyrrolidinyl]methanone

Conditions
ConditionsYield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 3-bromo-1-[(diphenylmethylene)amino]-2-piperidinone In tetrahydrofuran at -78℃; Inert atmosphere;
99%
1-benzofurane
271-89-6

1-benzofurane

triethylsilane
617-86-7

triethylsilane

2-(triethylsilyl)benzo[b]furan
60981-58-0

2-(triethylsilyl)benzo[b]furan

Conditions
ConditionsYield
With tert-butylethylene; C25H40O2P2Ru In neat (no solvent) at 120℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;98%
With norborn-2-ene; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;83%
With bis(norbornadiene)rhodium(l)tetrafluoroborate; 1,2-bis((2R,5R)-2,5-diisopropylphospholano)ethane; cyclohexene In neat (no solvent) at 80℃; for 20h; Solvent; Inert atmosphere; regioselective reaction;83%
With di-tert-butyl peroxide; copper diacetate In tert-butyl alcohol at 110℃; for 24h; Inert atmosphere;55%
With potassium tert-butylate In tetrahydrofuran at 60℃; for 45h; Inert atmosphere; Glovebox; regioselective reaction;38%
1-benzofurane
271-89-6

1-benzofurane

methanol
67-56-1

methanol

carbon tetrabromide
558-13-4

carbon tetrabromide

methyl benzofuran-2-carboxylate
1646-27-1

methyl benzofuran-2-carboxylate

Conditions
ConditionsYield
With ferrocene at 140℃; for 4h; Mechanism; Temperature; Reagent/catalyst; Inert atmosphere; sealed ampule; regioselective reaction;98%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; potassium carbonate at 20℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;70%
With Ru(2,2'-bipyridine)3(PF6)2*H2O; diisopropylamine at 20℃; for 36h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;40%
1-benzofurane
271-89-6

1-benzofurane

methyl iodide
74-88-4

methyl iodide

2-methylbenzofuran
4265-25-2

2-methylbenzofuran

Conditions
ConditionsYield
Stage #1: 1-benzofurane With tert.-butyl lithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
98%
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
88%
Stage #1: 1-benzofurane With tert.-butyl lithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #2: methyl iodide In tetrahydrofuran; hexane at 20℃; Inert atmosphere; Schlenk technique; Cooling;
87%
1-benzofurane
271-89-6

1-benzofurane

C13H14BNO6

C13H14BNO6

2-(4-(methoxycarbonyl)phenyl)benzo[b]furan
36078-99-6

2-(4-(methoxycarbonyl)phenyl)benzo[b]furan

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; C24H36N2O2Pd*2C2H4O2; cesium trifluoroacetate; trifluoroacetic acid; p-benzoquinone; silver(l) oxide In water at 30℃; for 20h; regioselective reaction;98%
1-benzofurane
271-89-6

1-benzofurane

1-Decene
872-05-9

1-Decene

2-decylbenzo[b]furan
151491-46-2

2-decylbenzo[b]furan

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); C29H41N2; sodium t-butanolate In neat (no solvent) at 50℃; for 16h; Reagent/catalyst; Temperature; Glovebox; Sealed tube;98%
1-benzofurane
271-89-6

1-benzofurane

triphenylmethane
519-73-3

triphenylmethane

2-tritylbenzofuran

2-tritylbenzofuran

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 100℃; for 6h; Inert atmosphere; Schlenk technique; Sealed tube;98%
1-benzofurane
271-89-6

1-benzofurane

2-(acetoxyphenylmethyl)-cyclohex-2-enone
94348-81-9

2-(acetoxyphenylmethyl)-cyclohex-2-enone

2-(1-benzofuran-2-yl-1-phenylmethyl)cyclohex-2-enone

2-(1-benzofuran-2-yl-1-phenylmethyl)cyclohex-2-enone

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 50℃; for 0.166667h; Friedel-Crafts Alkylation; regioselective reaction;98%
1-benzofurane
271-89-6

1-benzofurane

2,3-diethynylquinoxaline
91-19-0

2,3-diethynylquinoxaline

2,3-bis[benzo(b)furan-2-yl]quinoxaline

2,3-bis[benzo(b)furan-2-yl]quinoxaline

Conditions
ConditionsYield
Stage #1: 1-benzofurane With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃; for 1h; Inert atmosphere;
Stage #2: 2,3-diethynylquinoxaline In tetrahydrofuran; hexane at -78 - 20℃; for 11.5h; Inert atmosphere;
Stage #3: With iodine In tetrahydrofuran; hexane at 20℃; for 5h; Inert atmosphere;
98%
1-benzofurane
271-89-6

1-benzofurane

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(benzofuran-2-yl)trimethylsilane
60981-57-9

(benzofuran-2-yl)trimethylsilane

Conditions
ConditionsYield
With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78 - 20℃;97%
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere;
84%
Stage #1: 1-benzofurane With sodium 2,2,6,6-tetramethylpiperidide In hexane at 20℃; for 0.5h; Inert atmosphere; Sealed tube;
Stage #2: chloro-trimethyl-silane In hexane at 0 - 20℃; for 1h; Inert atmosphere; Sealed tube;
82%
1-benzofurane
271-89-6

1-benzofurane

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

2-(3,5-dimethylphenyl)-1,3-benzoxazole
154715-81-8

2-(3,5-dimethylphenyl)-1,3-benzoxazole

Conditions
ConditionsYield
With C13H18Cl2N4OPd; lithium tert-butoxide In N,N-dimethyl-formamide at 130℃; for 24h; Catalytic behavior; Inert atmosphere; Schlenk technique;97%
1-benzofurane
271-89-6

1-benzofurane

2,6-dimethyl-4-(2,2,2-trifluoro-1-phenylethylidene)cyclohexa-2,5-dienone

2,6-dimethyl-4-(2,2,2-trifluoro-1-phenylethylidene)cyclohexa-2,5-dienone

4-(1-(benzofuran-2-yl)-2,2,2-trifluoro-1-phenylethyl)-2,6-dimethylphenol

4-(1-(benzofuran-2-yl)-2,2,2-trifluoro-1-phenylethyl)-2,6-dimethylphenol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 0.166667h;97%
1-benzofurane
271-89-6

1-benzofurane

p-benzoquinone
106-51-4

p-benzoquinone

4-benzofuran-2-yl-4-hydroxy-cyclohexa-2,5-dienone

4-benzofuran-2-yl-4-hydroxy-cyclohexa-2,5-dienone

Conditions
ConditionsYield
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: p-benzoquinone In tetrahydrofuran
96%
1-benzofurane
271-89-6

1-benzofurane

o-bromobenzyl azide
126799-87-9

o-bromobenzyl azide

4-bromo-5,6,6a,11b-tetrahydrobenzofuro[2,3-c]quinoline

4-bromo-5,6,6a,11b-tetrahydrobenzofuro[2,3-c]quinoline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 0.25h; Aube-Schmidt rearrangement;96%
1-benzofurane
271-89-6

1-benzofurane

tert-butyl 6-bromopyridin-3-carboxylate
941294-58-2

tert-butyl 6-bromopyridin-3-carboxylate

tert-butyl 6-(benzofuran-2-yl)nicotinate
1393880-07-3

tert-butyl 6-(benzofuran-2-yl)nicotinate

Conditions
ConditionsYield
Stage #1: 1-benzofurane 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: tert-butyl 6-bromopyridin-3-carboxylate 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%
Stage #1: 1-benzofurane With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: tert-butyl 6-bromopyridin-3-carboxylate 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;
95%

Benzofuran Specification

The 2,3-Benzofuran is an organic compound with the formula C8H6O. The IUPAC name of this chemical is 1-benzofuran. With the CAS registry number 271-89-6, it is also named as Coumarone. The product's category is Furan & Benzofuran. Besides, it is colorless to light yellow liquid, which is used in the manufacture of synthetic resin. It is the fragrance intermediates, which is used for flavoring soap or washing powder.

Physical properties about 2,3-Benzofuran are: (1)ACD/LogP: 2.67; (2)ACD/LogD (pH 5.5): 2.67; (3)ACD/LogD (pH 7.4): 2.67; (4)ACD/BCF (pH 5.5): 62.98; (5)ACD/BCF (pH 7.4): 62.98; (6)ACD/KOC (pH 5.5): 675.27; (7)ACD/KOC (pH 7.4): 675.27; (8)#H bond acceptors: 1; (9)Polar Surface Area: 13.14 Å2; (10)Index of Refraction: 1.6; (11)Molar Refractivity: 36.39 cm3; (12)Molar Volume: 106.3 cm3; (13)Polarizability: 14.42×10-24cm3; (14)Surface Tension: 38.6 dyne/cm; (15)Density: 1.11 g/cm3; (16)Flash Point: 56.1 °C; (17)Enthalpy of Vaporization: 39.35 kJ/mol; (18)Boiling Point: 174 °C at 760 mmHg; (19)Vapour Pressure: 1.65 mmHg at 25°C.

Preparation: this chemical can be prepared by (2-formyl-phenoxy)-acetic acid. This reaction will need reagent sodium acηte, acetic acid anhydride and acetic acid.



Uses of 2,3-Benzofuran: it can be used to produce 2,3-dihydro-benzofuran. It will need reagent alcoholic potash.

When you are using this chemical, please be cautious about it as the following:
It is flammable and harmful to aquatic organisms. Please keep away from sources of ignition - No smoking. Besides, this chemical has limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing and gloves. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: o2c1ccccc1cc2
(2)InChI: InChI=1/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
(3)InChIKey: IANQTJSKSUMEQM-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
(5)Std. InChIKey: IANQTJSKSUMEQM-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 12, Pg. 383, 1977.

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