Product Name

  • Name

    2,3-Dihydrobenzofuran

  • EINECS 207-817-3
  • CAS No. 496-16-2
  • Article Data110
  • CAS DataBase
  • Density 1.096 g/cm3
  • Solubility
  • Melting Point -21 °C
  • Formula C8H8O
  • Boiling Point 188.2 °C at 760 mmHg
  • Molecular Weight 120.151
  • Flash Point 66.7 °C
  • Transport Information
  • Appearance colorless to light yellow liquid
  • Safety 23-24/25-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 496-16-2 (2,3-Dihydrobenzofuran)
  • Hazard Symbols IrritantXi
  • Synonyms Benzofuran,1,2-dihydro- (3CI);2,3-Dihydro-1-benzofuran;2,3-Dihydrobenzo[b]furan;Benzofuran,2,3-dihydro-;Benzodihydrofuran;Coumaran;Dihydrobenzofuran;Kumaran;
  • PSA 9.23000
  • LogP 1.62150

Synthetic route

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%
2-(2-iodophenyl)ethan-1-ol
26059-40-5

2-(2-iodophenyl)ethan-1-ol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With copper(l) iodide; sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Molecular sieve;99%
Multi-step reaction with 3 steps
1.1: triphenylphosphine; iodine; 1H-imidazole / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere; Darkness
2.1: silver(l) oxide / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
2.2: 0 - 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere
View Scheme
2-(2-chlorophenyl)-1-ethanol
19819-95-5

2-(2-chlorophenyl)-1-ethanol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With Ru/Al2O3; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h; Temperature; Microwave irradiation;96.2%
With copper(l) iodide; 8-quinolinol; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 120℃; Inert atmosphere;82%
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 23h;72%
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 23h;72%
With potassium phosphate; C22H28NP; palladium diacetate In toluene at 60℃; for 20h;51 % Chromat.
2-bromophenylethyl alcohol
1074-16-4

2-bromophenylethyl alcohol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With copper(l) iodide; lithium tert-butoxide In 1,4-dioxane at 100℃;96%
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 26h;87%
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 26h;87%
2-(2-hydroxyphenyl)ethanol
7768-28-7

2-(2-hydroxyphenyl)ethanol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With sodium methylate In carbonic acid dimethyl ester; acetonitrile for 2h; Inert atmosphere;95%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; carbonic acid dimethyl ester at 90℃; for 8h; Reagent/catalyst; Time;93%
Stage #1: 2-(2-hydroxyphenyl)ethanol With sodium hydride In mineral oil at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With trimethyl phosphite In mineral oil at 20℃; for 24h; Inert atmosphere;
90%
1-benzofurane
271-89-6

1-benzofurane

1,4,4a,9a-tetrahydro-fluorene
52652-40-1

1,4,4a,9a-tetrahydro-fluorene

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

9H-fluorene
86-73-7

9H-fluorene

Conditions
ConditionsYield
palladium on activated carbon at 250℃; for 2h;A 92%
B 95%
1-benzofurane
271-89-6

1-benzofurane

1,2,3,4-tetrahydro-9H-fluorene
17057-95-3

1,2,3,4-tetrahydro-9H-fluorene

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

9H-fluorene
86-73-7

9H-fluorene

Conditions
ConditionsYield
A 92%
B n/a
1-iodo-2-(2-iodo-ethoxy)-benzene

1-iodo-2-(2-iodo-ethoxy)-benzene

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
Stage #1: 1-iodo-2-(2-iodo-ethoxy)-benzene With isopropylmagnesium chloride In tetrahydrofuran at -30℃; for 1h;
Stage #2: In tetrahydrofuran at 25℃; for 2h;
Stage #3: In tetrahydrofuran
87%
2-(2-Bromoethyl)phenol
57027-75-5

2-(2-Bromoethyl)phenol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 3h; Heating;86%
With sodium hydroxide; benzene
With water
2-(2-bromophenoxy)ethyl 4-methylbenzenesulfonate
94897-00-4

2-(2-bromophenoxy)ethyl 4-methylbenzenesulfonate

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With copper(l) iodide; lithium methanolate; magnesium In tetrahydrofuran at 0℃; for 24h; Inert atmosphere; Schlenk technique;85%
2-(2-hydroxyphenyl)ethanol
7768-28-7

2-(2-hydroxyphenyl)ethanol

Vilsmeier reagent
3724-43-4, 149409-22-3

Vilsmeier reagent

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With triethylamine In dichloromethane Ambient temperature;80%
1-(2-bromoethoxy)-2-iodobenzene
57056-94-7

1-(2-bromoethoxy)-2-iodobenzene

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
Stage #1: 1-(2-bromoethoxy)-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at -30℃; for 1h;
Stage #2: In tetrahydrofuran at 25℃; for 2h;
Stage #3: In tetrahydrofuran
79%
2-bromophenyl 2-chloroethyl ether
64010-12-4

2-bromophenyl 2-chloroethyl ether

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

2-hydroxybromobenzene
95-56-7

2-hydroxybromobenzene

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
With magnesium; ethylene dibromide In tetrahydrofuranA 76%
B n/a
C n/a
5-methyl-1,10-phenanthroline
3002-78-6

5-methyl-1,10-phenanthroline

2-bromophenylethyl alcohol
1074-16-4

2-bromophenylethyl alcohol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With CuI; caesium carbonate In dodecane; toluene72%
1-(2-bromoethoxy)-2-bromobenzene
18800-28-7

1-(2-bromoethoxy)-2-bromobenzene

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -100 - -95℃; for 0.5h;69%
With diethyl ether; sodium
benzofuran-2(3H)-one
553-86-6

benzofuran-2(3H)-one

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With aluminium(III) triflate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 160℃; under 45603.1 Torr; for 12h; Autoclave;65%
Multi-step reaction with 2 steps
1: Lawesson's reagent / toluene / Heating
2: Raney nickel / diethyl ether / 1.) -15 deg C, 2.) -10 deg C, 2 min
View Scheme
2-(2-iodophenyl)ethyl tert-butyl peroxide
1592933-65-7

2-(2-iodophenyl)ethyl tert-butyl peroxide

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;58%
2-(2-hydroxyphenyl)ethanol
7768-28-7

2-(2-hydroxyphenyl)ethanol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

2-(2'-hydrophenyl)ethyl methyl carbonate

2-(2'-hydrophenyl)ethyl methyl carbonate

Conditions
ConditionsYield
With sodium methylate for 7h; Reflux; Inert atmosphere;A 55%
B 31%
With sodium methylate at 90℃; for 24h;A 6%
B 21%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

2-(2-hydroxyphenyl)ethanol
7768-28-7

2-(2-hydroxyphenyl)ethanol

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite at 0 - 50℃; for 1h;A 35%
B 50%
2-methoxyphenethyl alcohol
7417-18-7

2-methoxyphenethyl alcohol

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

2-(2-Bromoethyl)phenol
57027-75-5

2-(2-Bromoethyl)phenol

Conditions
ConditionsYield
With hydrogen bromide; acetic acidA 36%
B 46%
1-benzofurane
271-89-6

1-benzofurane

A

o-Hydroxyethylbenzene
90-00-6

o-Hydroxyethylbenzene

B

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With 15-crown-5; sodium; isopropyl alcohol In tetrahydrofuran at 0℃; for 0.0833333h; Birch Reduction; chemoselective reaction;A 42%
B 39%
With ethanol; sodium
With ethanol; sodium
With 15-crown-5; sodium In tetrahydrofuran; isopropyl alcohol; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; Overall yield = 75 %; Overall yield = 45 mg;
1-bromo-2-methoxy-3-methylbenzene
52200-69-8

1-bromo-2-methoxy-3-methylbenzene

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With palladium(0)bis(tricyclohexylphosphine); cesium pivalate In toluene at 140℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;40%
1-benzofurane
271-89-6

1-benzofurane

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

4,7-dihydrobenzofuran
99636-24-5

4,7-dihydrobenzofuran

Conditions
ConditionsYield
With sodium In methanol; diethyl ether; ammonia for 0.166667h;A 34%
B 36%
With tetrabutylammonium tetrafluoroborate In tetrahydrofuran; water at 0℃; electrolysis (mercury cathode, platinum flag anode, silver wire reference electrode, constant current 4-32 mA cm-2); Yield given. Yields of byproduct given;
3,4-epoxy-chroman
6538-94-9

3,4-epoxy-chroman

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
In cyclohexane for 6h; Ambient temperature; Irradiation;36%
(Trimethylsilyl)(o-methoxyphenyl)methanol
75311-63-6

(Trimethylsilyl)(o-methoxyphenyl)methanol

A

1-benzofurane
271-89-6

1-benzofurane

B

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
In benzene at 600℃;A 16%
B 28%
[(2-Methoxy-phenyl)-phenylmethanesulfonyl-methylene]-triphenyl-λ5-phosphane
134749-74-9

[(2-Methoxy-phenyl)-phenylmethanesulfonyl-methylene]-triphenyl-λ5-phosphane

A

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

B

(E)-2-methoxystilbene
52805-92-2

(E)-2-methoxystilbene

C

(Z)-1-(2-methoxyphenyl)-2-phenylethene
1898-14-2

(Z)-1-(2-methoxyphenyl)-2-phenylethene

D

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
ConditionsYield
at 600℃; under 0.001 - 0.1 Torr; for 1h; Yields of byproduct given. Title compound not separated from byproducts;A 7%
B n/a
C n/a
D 11 % Spectr.
2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With zinc(II) chloride
With manganese(ll) chloride; zinc(II) chloride at 200℃; for 3h; Temperature;
1-(2-bromoethoxy)-2-chlorobenzene
18800-26-5

1-(2-bromoethoxy)-2-chlorobenzene

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With diethyl ether; sodium
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite Erwaermen der Diazoniumsalz-Loesung mit Natiumhydrogencabonat;
Multi-step reaction with 2 steps
1: 50 percent / aq. sodium nitrite, conc. sulfuric acid / 1 h / 0 - 50 °C
2: 75 percent / alumina-silica / 1,2-dimethoxy-ethane / 1 h / 250 °C
View Scheme
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

5-bromo-2,3-dihydrobenzo[b]furan
66826-78-6

5-bromo-2,3-dihydrobenzo[b]furan

Conditions
ConditionsYield
With bromine100%
With iron(III) chloride; N-Bromosuccinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In toluene at 40℃; regioselective reaction;98%
With bromine In dichloromethane for 0.5h; Ambient temperature;96%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,3-dihydro-benzofuran-5-carbaldehyde
55745-70-5

2,3-dihydro-benzofuran-5-carbaldehyde

Conditions
ConditionsYield
With trichlorophosphate at 70 - 90℃; for 9.5h;100%
With trichlorophosphate at 70 - 90℃; for 9.5h;100%
Stage #1: 2.3-dihydrobenzofuran; N,N-dimethyl-formamide With trichlorophosphate at 30 - 70℃;
Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h;
98%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

2,3-dihydro-benzofuran-5-carbaldehyde
55745-70-5

2,3-dihydro-benzofuran-5-carbaldehyde

Conditions
ConditionsYield
With trichlorophosphate In water; N,N-dimethyl-formamide100%
With trichlorophosphate In water; N,N-dimethyl-formamide100%
With sodium hydrogencarbonate; trichlorophosphate In N,N-dimethyl-formamide94%
Multi-step reaction with 2 steps
1: 100 percent / Br2
2: 98 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C
View Scheme
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

2,3-dihydrobenzofuran-5-sulfonyl chloride
115010-11-2

2,3-dihydrobenzofuran-5-sulfonyl chloride

Conditions
ConditionsYield
Stage #1: 2.3-dihydrobenzofuran With sulfur trioxide-N,N-dimethylformamide complex In 1,2-dichloro-ethane at 85℃; for 1h;
Stage #2: With thionyl chloride In 1,2-dichloro-ethane at 20 - 75℃; for 1h;
100%
Stage #1: 2.3-dihydrobenzofuran With sulfur trioxide-N,N-dimethylformamide complex In 1,2-dichloro-ethane at 85℃; for 1h;
Stage #2: With thionyl chloride In 1,2-dichloro-ethane at 20 - 75℃; for 1h;
100%
In 1,2-dichloro-ethane94%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

acetyl chloride
75-36-5

acetyl chloride

1-(2,3-dihydrobenzofuran-5-yl)ethanone
90843-31-5

1-(2,3-dihydrobenzofuran-5-yl)ethanone

Conditions
ConditionsYield
aluminum (III) chloride In dichloromethane at -10℃; for 0.5h;99%
With aluminum (III) chloride In dichloromethane at -10℃; for 0.5h;99%
With aluminum (III) chloride In dichloromethane at -10℃; for 3h;97%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

5-iodo-2,3-dihydro-1-benzofuran
132464-84-7

5-iodo-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
With N-iodo-succinimide; silver(I) triflimide In dichloromethane at 36℃; for 1h; Darkness;99%
With indium(III) triflate; N-iodo-succinimide In acetonitrile at 23℃; for 8h; Inert atmosphere; Darkness;92%
With iron(III) chloride; N-iodo-succinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 36℃; for 1h; Inert atmosphere;91%
triethylsilane
617-86-7

triethylsilane

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

triethyl-(2-ethyl-phenoxy)-silane

triethyl-(2-ethyl-phenoxy)-silane

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 20h; silylation;99%
With tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 20h; Reduction; dehydrocondensation;99%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

2,3-dihydrobenzofuran-5-sulfonyl chloride
115010-11-2

2,3-dihydrobenzofuran-5-sulfonyl chloride

Conditions
ConditionsYield
With thionyl chloride In water99%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

2-trimethylsilyl ethane sulfonic acid azide
871949-46-1

2-trimethylsilyl ethane sulfonic acid azide

C13H21NO3SSi

C13H21NO3SSi

Conditions
ConditionsYield
Stage #1: 2.3-dihydrobenzofuran; 2-trimethylsilyl ethane sulfonic acid azide In neat (no solvent) at -10℃; for 0.5h; Schlenk technique; Inert atmosphere; Molecular sieve;
Stage #2: With C61H40F4N2O3Ru In neat (no solvent) at -10℃; for 2h; Schlenk technique; Inert atmosphere; Molecular sieve; enantioselective reaction;
99%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

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 C25H40O2P2Ru In octane at 150℃; for 12h; Inert atmosphere;99%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

propionyl chloride
79-03-8

propionyl chloride

1-(2,3-dihydrobenzofuran-5-yl)propan-1-one
68660-11-7

1-(2,3-dihydrobenzofuran-5-yl)propan-1-one

Conditions
ConditionsYield
Stage #1: propionyl chloride; aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 2.3-dihydrobenzofuran In dichloromethane at 0℃; Inert atmosphere;
98%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 1h;80%
With tin(IV) chloride In benzene at 30℃; for 24h; Friedel-Crafts acylation;66%
With carbon disulfide; aluminium trichloride
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

2,3-dihydrobenzofuran-5-sulfonic acid

2,3-dihydrobenzofuran-5-sulfonic acid

Conditions
ConditionsYield
With sulfur trioxide In nitromethane at 0℃; for 1h;98%
With sulfur trioxide In nitromethane at 0℃;
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

2,3-Dihydro-benzofuran-5,7-disulfonic acid

2,3-Dihydro-benzofuran-5,7-disulfonic acid

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 3600h; other reagent; other solvent; other temp;98%
With sulfur trioxide In nitromethane at 0℃; excess of reagent;
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

norbornene
498-66-8

norbornene

7-(bicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1-benzofuran

7-(bicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1-benzofuran

Conditions
ConditionsYield
With (C5H5)Y(CH2C6H4NMe2-o)2; trityl tetrakis(pentafluorophenyl)borate In toluene at 70℃; for 24h; Inert atmosphere; Glovebox; regioselective reaction;98%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

benzoic acid
65-85-0

benzoic acid

(2,3-dihydrobenzofuran-5-yl)(phenyl)methanone
115063-19-9

(2,3-dihydrobenzofuran-5-yl)(phenyl)methanone

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride at 20℃; for 12h; Friedel-Crafts Acylation; Inert atmosphere;98%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

(2,3-dihydro-1-benzofuran-5-yl)(4′-methoxyphenyl)sulfane

(2,3-dihydro-1-benzofuran-5-yl)(4′-methoxyphenyl)sulfane

Conditions
ConditionsYield
With tetrabutylammonium acetate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction;97%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

bis(2,2,2-trichloroethyl) hydrazino-1,2-dicarboxylate
38858-02-5

bis(2,2,2-trichloroethyl) hydrazino-1,2-dicarboxylate

1-(5-dihydrobenzofuranyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester
197590-43-5

1-(5-dihydrobenzofuranyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester

Conditions
ConditionsYield
With zinc(II) chloride In dichloromethane at 20℃;96.6%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

5-Chloro-2,3-dihydrobenzo[b]furan
76429-69-1

5-Chloro-2,3-dihydrobenzo[b]furan

Conditions
ConditionsYield
With N-chloro-succinimide; 2,2,6,6-tetramethylpiperidin-1-oxoammonium trifluoromethanesulfonate In chloroform at 25℃; for 12h; Reagent/catalyst; Schlenk technique;96%
With iron(III) chloride; N-chloro-succinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In tetrahydrofuran at 60℃; for 18h; Inert atmosphere; regioselective reaction;86%
With N-chloro-succinimide; zirconium(IV) chloride In dichloromethane at 20℃; for 12h;
With N-chloro-succinimide; zirconium(IV) chloride In dichloromethane at 20℃; for 12h; Conversion of starting material;
With N-chloro-succinimide; acetic acid In acetonitrile at 10 - 35℃; for 48h;2.28 g
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

acetic anhydride
108-24-7

acetic anhydride

1-(2,3-dihydrobenzofuran-5-yl)ethanone
90843-31-5

1-(2,3-dihydrobenzofuran-5-yl)ethanone

Conditions
ConditionsYield
With Hβ zeolite (Si:Al 12.5) at 120℃; for 1.5h;95%
With trifluoroacetic acid at 20℃; for 1.5h; Friedel-Crafts Acylation;91%
With zinc(II) chloride at 95 - 105℃; for 10h;
With zinc(II) chloride at 95 - 105℃; for 10h;
3,5-bis(trifluoromethyl)phenyl azide

3,5-bis(trifluoromethyl)phenyl azide

2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

C16H11F6NO

C16H11F6NO

Conditions
ConditionsYield
With chloro[5,10,15,20-tetrakis(4-dimethylamino-2,3,5,6-tetrafluorophenyl)porphyrinate]iron(III) In 1,2-dichloro-ethane at 120℃; for 12h; Schlenk technique; Inert atmosphere; Molecular sieve; regioselective reaction;95%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

2,3-dihydrobenzofuran-7-sulfonyl chloride
953408-82-7

2,3-dihydrobenzofuran-7-sulfonyl chloride

Conditions
ConditionsYield
In 1,2-dichloro-ethane94%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

1-(2,3-dihydrobenzofuran-5-yl)ethanone
90843-31-5

1-(2,3-dihydrobenzofuran-5-yl)ethanone

Conditions
ConditionsYield
Stage #1: acetyl chloride With aluminum (III) chloride In dichloromethane at -10℃; for 0.25h;
Stage #2: 2.3-dihydrobenzofuran In dichloromethane at -10℃; for 0.5h;
Stage #3: With hydrogenchloride In dichloromethane; water at 0℃; for 2h;
94%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

5,7-Dibromo-2,3-dihydrobenzofuran
123266-59-1

5,7-Dibromo-2,3-dihydrobenzofuran

Conditions
ConditionsYield
With bromine; sodium thiosulfate In dichloromethane; acetic acid93%
With iodine pentoxide; potassium bromide In water at 20℃; for 23h; regioselective reaction;89%
With bromine; sodium thiosulfate In chloroform87%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

5-Chlorovaleroyl chloride
1575-61-7

5-Chlorovaleroyl chloride

5-Chloro-1-(2,3-dihydro-1-benzofuran-5-yl)-1-pentanone

5-Chloro-1-(2,3-dihydro-1-benzofuran-5-yl)-1-pentanone

Conditions
ConditionsYield
Stage #1: 2.3-dihydrobenzofuran; aluminum (III) chloride In toluene at 20 - 30℃; for 0.5h;
Stage #2: 5-Chlorovaleroyl chloride In toluene at -5 - 5℃; for 1h;
92.8%

2,3-Dihydrobenzofuran Chemical Properties

Molecular Structure of 2,3-Dihydrobenzofuran (CAS NO.496-16-2):

IUPAC Name: 2,3-Dihydro-1-benzofuran
Molecular Formula: C8H8O
Molecular Weight: 120.148520 g/mol
Molar Refractivity: 35.42 cm3
Molar Volume: 109.5 cm3
Surface Tension: 41.4 dyne/cm
Density: 1.096 g/cm3
Melting Point: -21 °C
Flash Point: 66.7 °C
Boiling Point: 188.2 °C at 760 mmHg
Enthalpy of Vaporization: 40.7 kJ/mol
Vapour Pressure: 0.836 mmHg at 25 °C
XLogP3: 2.1
H-Bond Acceptor: 1
Exact Mass: 120.057515
MonoIsotopic Mass: 120.057515
Topological Polar Surface Area: 9.2
Heavy Atom Count: 9 
Canonical SMILES: C1COC2=CC=CC=C21
InChI: InChI=1S/C8H8O/c1-2-4-8-7(3-1)5-6-9-8/h1-4H,5-6H2
InChIKey: HBEDSQVIWPRPAY-UHFFFAOYSA-N
EINECS: 207-817-3
Product Categories: Fluorobenzene; Benzodiozoles, Benzodioxines & Benzodioxepines; Furan&Benzofuran; Benzodiozoles, Benzodioxines & Benzodioxepines

2,3-Dihydrobenzofuran Safety Profile

Hazard Codes: Xi
Hazard Note: Irritant
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 23-24/25-26
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24/25: Avoid contact with skin and eyes
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 3
HS Code: 29329995

2,3-Dihydrobenzofuran Specification

 2,3-Dihydrobenzofuran (CAS NO.496-16-2) is also named as Coumaran ; Benzofuran, 2,3-dihydro- ; 2,3-Dihydro-1-benzofuran ; Dihydrocoumarone . 2,3-Dihydrobenzofuran (CAS NO.496-16-2) is colorless to light yellow liquid.

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