Conditions | Yield |
---|---|
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
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
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
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
1,4,4a,9a-tetrahydro-fluorene
A
2,3-Dihydrobenzofuran
B
9H-fluorene
Conditions | Yield |
---|---|
palladium on activated carbon at 250℃; for 2h; | A 92% B 95% |
1-benzofurane
1,2,3,4-tetrahydro-9H-fluorene
A
2,3-Dihydrobenzofuran
B
9H-fluorene
Conditions | Yield |
---|---|
A 92% B n/a |
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
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
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 3h; Heating; | 86% |
With sodium hydroxide; benzene | |
With water |
2-(2-bromophenoxy)ethyl 4-methylbenzenesulfonate
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With copper(l) iodide; lithium methanolate; magnesium In tetrahydrofuran at 0℃; for 24h; Inert atmosphere; Schlenk technique; | 85% |
2-(2-hydroxyphenyl)ethanol
Vilsmeier reagent
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Ambient temperature; | 80% |
1-(2-bromoethoxy)-2-iodobenzene
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
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
A
2,3-Dihydrobenzofuran
B
2-hydroxybromobenzene
C
phenol
Conditions | Yield |
---|---|
With magnesium; ethylene dibromide In tetrahydrofuran | A 76% B n/a C n/a |
5-methyl-1,10-phenanthroline
2-bromophenylethyl alcohol
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With CuI; caesium carbonate In dodecane; toluene | 72% |
1-(2-bromoethoxy)-2-bromobenzene
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -100 - -95℃; for 0.5h; | 69% |
With diethyl ether; sodium |
Conditions | Yield |
---|---|
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
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere; | 58% |
2-(2-hydroxyphenyl)ethanol
carbonic acid dimethyl ester
A
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
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
A
2,3-Dihydrobenzofuran
B
2-(2-hydroxyphenyl)ethanol
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite at 0 - 50℃; for 1h; | A 35% B 50% |
2-methoxyphenethyl alcohol
A
2,3-Dihydrobenzofuran
B
2-(2-Bromoethyl)phenol
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid | A 36% B 46% |
Conditions | Yield |
---|---|
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
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With palladium(0)bis(tricyclohexylphosphine); cesium pivalate In toluene at 140℃; for 16h; Inert atmosphere; Sealed tube; Glovebox; | 40% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In cyclohexane for 6h; Ambient temperature; Irradiation; | 36% |
(Trimethylsilyl)(o-methoxyphenyl)methanol
A
1-benzofurane
B
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
In benzene at 600℃; | A 16% B 28% |
[(2-Methoxy-phenyl)-phenylmethanesulfonyl-methylene]-triphenyl-λ5-phosphane
A
2,3-Dihydrobenzofuran
B
(E)-2-methoxystilbene
C
(Z)-1-(2-methoxyphenyl)-2-phenylethene
D
1,1'-(1,2-ethanediyl)bisbenzene
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
With zinc(II) chloride | |
With manganese(ll) chloride; zinc(II) chloride at 200℃; for 3h; Temperature; |
1-(2-bromoethoxy)-2-chlorobenzene
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With diethyl ether; sodium |
Conditions | Yield |
---|---|
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
5-bromo-2,3-dihydrobenzo[b]furan
Conditions | Yield |
---|---|
With bromine | 100% |
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
N,N-dimethyl-formamide
2,3-dihydro-benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
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
2,3-dihydro-benzofuran-5-carbaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate In water; N,N-dimethyl-formamide | 100% |
With trichlorophosphate In water; N,N-dimethyl-formamide | 100% |
With sodium hydrogencarbonate; trichlorophosphate In N,N-dimethyl-formamide | 94% |
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
2,3-dihydrobenzofuran-5-sulfonyl chloride
Conditions | Yield |
---|---|
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-ethane | 94% |
2,3-Dihydrobenzofuran
acetyl chloride
1-(2,3-dihydrobenzofuran-5-yl)ethanone
Conditions | Yield |
---|---|
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
5-iodo-2,3-dihydro-1-benzofuran
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
1,2-dichloro-ethane
2,3-dihydrobenzofuran-5-sulfonyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In water | 99% |
Conditions | Yield |
---|---|
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
bis(pinacol)diborane
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan
Conditions | Yield |
---|---|
With C25H40O2P2Ru In octane at 150℃; for 12h; Inert atmosphere; | 99% |
2,3-Dihydrobenzofuran
propionyl chloride
1-(2,3-dihydrobenzofuran-5-yl)propan-1-one
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With sulfur trioxide In nitromethane at 0℃; for 1h; | 98% |
With sulfur trioxide In nitromethane at 0℃; |
2,3-Dihydrobenzofuran
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 3600h; other reagent; other solvent; other temp; | 98% |
With sulfur trioxide In nitromethane at 0℃; excess of reagent; |
Conditions | Yield |
---|---|
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
benzoic acid
(2,3-dihydrobenzofuran-5-yl)(phenyl)methanone
Conditions | Yield |
---|---|
With trifluoroacetic acid; trifluoroacetic anhydride at 20℃; for 12h; Friedel-Crafts Acylation; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With tetrabutylammonium acetate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction; | 97% |
2,3-Dihydrobenzofuran
bis(2,2,2-trichloroethyl) hydrazino-1,2-dicarboxylate
1-(5-dihydrobenzofuranyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester
Conditions | Yield |
---|---|
With zinc(II) chloride In dichloromethane at 20℃; | 96.6% |
2,3-Dihydrobenzofuran
5-Chloro-2,3-dihydrobenzo[b]furan
Conditions | Yield |
---|---|
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
acetic anhydride
1-(2,3-dihydrobenzofuran-5-yl)ethanone
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
2,3-dihydrobenzofuran-7-sulfonyl chloride
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane | 94% |
2,3-Dihydrobenzofuran
1-(2,3-dihydrobenzofuran-5-yl)ethanone
Conditions | Yield |
---|---|
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
5,7-Dibromo-2,3-dihydrobenzofuran
Conditions | Yield |
---|---|
With bromine; sodium thiosulfate In dichloromethane; acetic acid | 93% |
With iodine pentoxide; potassium bromide In water at 20℃; for 23h; regioselective reaction; | 89% |
With bromine; sodium thiosulfate In chloroform | 87% |
Conditions | Yield |
---|---|
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% |
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
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 (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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