1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one supplier

Name
1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one
EINECS 1308068-626-2
CAS No. 196597-78-1
Article Data20
CAS DataBase
Density 1.289 g/cm³
Solubility
Melting Point 149-151 °C
Formula C₁₁H₁₀O₂
Boiling Point 334.156 °C at 760 mmHg
Molecular Weight 174.199
Flash Point 165.595 °C
Transport Information
Appearance White solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 6,7-Dihydro-1H-indeno[5,4-b]furan-8(2H)-one;
PSA 26.30000
LogP 1.75040

Synthetic route

: 1205098-83-4
1-(2,3-dihydrobenzofuran-4-yl)-2-propen-1-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 10 - 20℃; for 16h; Solvent; Reagent/catalyst;	96.3%
With sulfuric acid In pentane at 67℃; Product distribution / selectivity; Inert atmosphere;
With sulfuric acid In water; pentane at 67℃; for 0.5h; Inert atmosphere;

: 196597-77-0
4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
With hydrogen; acetic acid; 10percent Pd/C/H2O at 20℃; for 1h;	89%
With hydrogen; sodium acetate; 5% palladium over charcoal In water; acetic acid at 20℃;	89%
With hydrogen; sodium acetate; palladium 10% on activated carbon In methanol at 40℃; under 2175.22 - 3675.37 Torr; for 8h;	88.6%

: 196597-77-0
4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

A: 1092507-06-6
C11H12O

B: 1092507-07-7
2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-ol

C: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
With hydrogen; sodium acetate; acetic acid; palladium 10% on activated carbon under 1471.14 - 2206.72 Torr;	A n/a B n/a C 85%

...Expand

: 15480-25-8
6,7-dihydro-8H-indeno-[5,4-b]furan-8-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
With hydrogen; 5% Pd(II)/C(eggshell); triethylamine In tetrahydrofuran; ethanol at 35℃; under 4500.45 - 5250.53 Torr; for 24h;	62%

: 1198465-69-8
4-tert-butyl-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
With hydrogenchloride; aluminum (III) chloride In benzene	20%

: 496-16-2
2,3-Dihydrobenzofuran

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 92 percent / TiCl4 / CH2Cl2 / 1 h 2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 2.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 3.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 4.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 5.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 6.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 7.1: SOCl2 / 75 °C 8.1: AlCl3 / 1,2-dichloro-ethane / 20 °C 9.1: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1.1: 86 percent / POCl3 / 12 h / 80 - 85 °C 2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 2.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 3.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 4.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 5.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 6.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 7.1: SOCl2 / 75 °C 8.1: AlCl3 / 1,2-dichloro-ethane / 20 °C 9.1: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: trichlorophosphate / 5.17 h / 30 - 98 °C 2.1: sodium methylate / toluene / 0.25 h / 0 - 30 °C 3.1: hydrogen / nickel / methanol / 4 h / 50 °C 4.1: bromine; sodium acetate; acetic acid / 14 h / 20 - 28 °C 5.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C 5.2: 1 h / -5 - 5 °C 6.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C View Scheme

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

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 1.2: 88 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 3.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 4.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 5.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 6.1: SOCl2 / 75 °C 7.1: AlCl3 / 1,2-dichloro-ethane / 20 °C 8.1: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium methylate / toluene / 0.25 h / 0 - 30 °C 2.1: hydrogen / nickel / methanol / 4 h / 50 °C 3.1: bromine; sodium acetate; acetic acid / 14 h / 20 - 28 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C 4.2: 1 h / -5 - 5 °C 5.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C View Scheme
Multi-step reaction with 6 steps 1.1: piperidine; pyridine / 6 h / 120 °C 2.1: thionyl chloride / 0.67 h / 26 - 73 °C / Heating / reflux 3.1: hydrogen / nickel / methanol / 4 h / 50 °C 4.1: bromine; sodium acetate; acetic acid / 14 h / 20 - 28 °C 5.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C 5.2: 1 h / -5 - 5 °C 6.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C View Scheme
Multi-step reaction with 5 steps 1.1: piperidine; pyridine; acetic acid / 4 - 5 h / 100 °C 1.2: 2 - 3 h / 20 °C 2.1: sodium hydroxide; hydrogen; ammonium formate / palladium 10% on activated carbon / water / 5 - 6 h / 20 °C 3.1: bromine; sodium acetate; acetic acid / 2 - 3 h / 0 - 45 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / 1 - 2 h / 20 °C 4.2: 1 - 2 h / 0 - 5 °C 5.1: hydrogen; sodium acetate; acetic acid / palladium 10% on activated carbon / 1471.14 - 2206.72 Torr View Scheme
Multi-step reaction with 6 steps 1: sodium t-butanolate / toluene / 1 h 2: acetic acid; hydrogen; 5%-palladium/activated carbon / 1 h / 50 °C / 1470.15 - 2205.22 Torr 3: acetic acid; sodium acetate; bromine / 6 h / 20 °C / Cooling 4: thionyl chloride / 1,2-dichloro-benzene; N,N-dimethyl-formamide / 42 °C 5: aluminum (III) chloride / 0.5 h / Cooling with ice 6: hydrogen; sodium acetate; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 2205.22 - 3675.37 Torr View Scheme

: 196597-65-6
ethyl (E)-3-(2,3-dihydrobenzofuran-5-yl)-2-propenoate

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 2: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 3: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 4: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 5: SOCl2 / 75 °C 6: AlCl3 / 1,2-dichloro-ethane / 20 °C 7: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: acetic acid; hydrogen; 5%-palladium/activated carbon / 1 h / 50 °C / 1470.15 - 2205.22 Torr 2: acetic acid; sodium acetate; bromine / 6 h / 20 °C / Cooling 3: thionyl chloride / 1,2-dichloro-benzene; N,N-dimethyl-formamide / 42 °C 4: aluminum (III) chloride / 0.5 h / Cooling with ice 5: hydrogen; sodium acetate; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 2205.22 - 3675.37 Torr View Scheme

Yield

Multi-step reaction with 7 steps
1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C
2: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C
3: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C
4: 93 percent / aq. KOH / ethanol / 1 h / 90 °C
5: SOCl2 / 75 °C
6: AlCl3 / 1,2-dichloro-ethane / 20 °C
7: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C
View Scheme

Multi-step reaction with 5 steps
1: acetic acid; hydrogen; 5%-palladium/activated carbon / 1 h / 50 °C / 1470.15 - 2205.22 Torr
2: acetic acid; sodium acetate; bromine / 6 h / 20 °C / Cooling
3: thionyl chloride / 1,2-dichloro-benzene; N,N-dimethyl-formamide / 42 °C
4: aluminum (III) chloride / 0.5 h / Cooling with ice
5: hydrogen; sodium acetate; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 2205.22 - 3675.37 Torr
View Scheme

: 196597-66-7
ethyl 3-(2,3-dihydro-1-benzofuran-5-yl)propanoate

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 2: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 3: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 4: SOCl2 / 75 °C 5: AlCl3 / 1,2-dichloro-ethane / 20 °C 6: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: bromine; sodium acetate; acetic acid / 14 h / 20 - 28 °C 2.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C 2.2: 1 h / -5 - 5 °C 3.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C View Scheme
Multi-step reaction with 4 steps 1: acetic acid; sodium acetate; bromine / 6 h / 20 °C / Cooling 2: thionyl chloride / 1,2-dichloro-benzene; N,N-dimethyl-formamide / 42 °C 3: aluminum (III) chloride / 0.5 h / Cooling with ice 4: hydrogen; sodium acetate; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 2205.22 - 3675.37 Torr View Scheme

: 196597-67-8
ethyl 3-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 2: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 3: SOCl2 / 75 °C 4: AlCl3 / 1,2-dichloro-ethane / 20 °C 5: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme

: 227179-21-7
3-(6,7-dibromo-2,3-dihydro-benzofuran-5-yl)-propionyl chloride

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3 / 1,2-dichloro-ethane / 20 °C 2: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 0.5 h / Cooling with ice 2: hydrogen; sodium acetate; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 2205.22 - 3675.37 Torr View Scheme

: 196597-76-9
ethyl 3-(6,7-dibromo-2,3-dihydrobenzofuran-5-yl) propionic acid

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / 75 °C 2: AlCl3 / 1,2-dichloro-ethane / 20 °C 3: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C 1.2: 1 h / -5 - 5 °C 2.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 1 - 2 h / 20 °C 1.2: 1 - 2 h / 0 - 5 °C 2.1: hydrogen; sodium acetate; acetic acid / palladium 10% on activated carbon / 1471.14 - 2206.72 Torr View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / 1,2-dichloro-benzene; N,N-dimethyl-formamide / 42 °C 2: aluminum (III) chloride / 0.5 h / Cooling with ice 3: hydrogen; sodium acetate; palladium 10% on activated carbon / methanol / 2 h / 40 °C / 2205.22 - 3675.37 Torr View Scheme

: 196597-75-8
ethyl 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoate

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 2: SOCl2 / 75 °C 3: AlCl3 / 1,2-dichloro-ethane / 20 °C 4: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme

: 1198465-72-3
6-hydroxy-7-(2-mesyloxyethyl)indan-1-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
With triethylamine In ethyl acetate for 3h; Reflux;	4.47 g

: 50-00-0
formaldehyd

: 1205098-82-3
1-(dihydrobenzofuran-4-yl)ethanone

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Stage #1: formaldehyd; 1-(dihydrobenzofuran-4-yl)ethanone With dicyclohexylammonium trifloroacetate In 1,4-dioxane at 100℃; for 4h; Stage #2: With sulfuric acid In pentane at 67℃; Inert atmosphere;

: 62803-47-8
6-hydroxy-1-indanone

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 5 h / Reflux 2.1: N,N-dimethyl-aniline / Inert atmosphere; Reflux 2.2: 25 °C 3.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere 3.2: 20 °C 4.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux 5.1: hydrogen / triethylamine; 5% Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr View Scheme

Yield

Multi-step reaction with 5 steps
1.1: potassium carbonate / acetone / 5 h / Reflux
2.1: N,N-dimethyl-aniline / Inert atmosphere; Reflux
2.2: 25 °C
3.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere
3.2: 20 °C
4.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux
5.1: hydrogen / triethylamine; 5% Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr
View Scheme

: 6-allyloxy-indan-1-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-aniline / Inert atmosphere; Reflux 1.2: 25 °C 2.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere 2.2: 20 °C 3.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux 4.1: hydrogen / triethylamine; 5% Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr View Scheme

: 6-hydroxy-7-allyl-indan-1-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere 1.2: 20 °C 2.1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux 3.1: hydrogen / triethylamine; 5% Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr View Scheme

: 1290145-09-3
2-methoxy-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 0.75 h / Reflux 2: hydrogen / triethylamine; 5% Pd(II)/C(eggshell) / ethanol; tetrahydrofuran / 24 h / 35 °C / 4500.45 - 5250.53 Torr View Scheme

: 198707-57-2
3-(2,3-dihydro-1-benzofuran-5-yl)prop-2-enoic acid

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: thionyl chloride / 0.67 h / 26 - 73 °C / Heating / reflux 2.1: hydrogen / nickel / methanol / 4 h / 50 °C 3.1: bromine; sodium acetate; acetic acid / 14 h / 20 - 28 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C 4.2: 1 h / -5 - 5 °C 5.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydroxide; hydrogen; ammonium formate / palladium 10% on activated carbon / water / 5 - 6 h / 20 °C 2.1: bromine; sodium acetate; acetic acid / 2 - 3 h / 0 - 45 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / 1 - 2 h / 20 °C 3.2: 1 - 2 h / 0 - 5 °C 4.1: hydrogen; sodium acetate; acetic acid / palladium 10% on activated carbon / 1471.14 - 2206.72 Torr View Scheme

Yield

Multi-step reaction with 5 steps
1.1: thionyl chloride / 0.67 h / 26 - 73 °C / Heating / reflux
2.1: hydrogen / nickel / methanol / 4 h / 50 °C
3.1: bromine; sodium acetate; acetic acid / 14 h / 20 - 28 °C
4.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C
4.2: 1 h / -5 - 5 °C
5.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C
View Scheme

Multi-step reaction with 4 steps
1.1: sodium hydroxide; hydrogen; ammonium formate / palladium 10% on activated carbon / water / 5 - 6 h / 20 °C
2.1: bromine; sodium acetate; acetic acid / 2 - 3 h / 0 - 45 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / 1 - 2 h / 20 °C
3.2: 1 - 2 h / 0 - 5 °C
4.1: hydrogen; sodium acetate; acetic acid / palladium 10% on activated carbon / 1471.14 - 2206.72 Torr
View Scheme

: 217483-05-1
ethyl 3-(2,3-dihydrobenzofuran-5-yl)acrylate

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogen / nickel / methanol / 4 h / 50 °C 2.1: bromine; sodium acetate; acetic acid / 14 h / 20 - 28 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / 1,2-dichloro-benzene / 2 h / 28 - 60 °C 3.2: 1 h / -5 - 5 °C 4.1: hydrogen; sodium acetate / raney chloride / methanol / 50 °C View Scheme

: 215057-28-6
3-(2,3-dihydro-1-benzofuran-5-yl)propanoic acid

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine; sodium acetate; acetic acid / 2 - 3 h / 0 - 45 °C 2.1: thionyl chloride / N,N-dimethyl-formamide / 1 - 2 h / 20 °C 2.2: 1 - 2 h / 0 - 5 °C 3.1: hydrogen; sodium acetate; acetic acid / palladium 10% on activated carbon / 1471.14 - 2206.72 Torr View Scheme

: 209256-42-8
2,3-dihydro-1-benzofuran-4-carbaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 6.5 h / -10 - 20 °C 2: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 3: copper(II) bis(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 16 h / 10 - 20 °C View Scheme

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 1092507-07-7
2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 6h;	100%

: 104-88-1
4-chlorobenzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(4-chlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.366667h; Green chemistry;	98%

: 387-45-1
2-chloro-6-fluorobenzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(2-chloro-6-fluorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.166667h; Green chemistry;	98%
With sodium hydroxide In water

: 89-98-5
2-chloro-benzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(2-chlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.333333h; Green chemistry;	97%
With sodium hydroxide In water

: 6334-18-5
2,3-dichlorobenzylaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(2,3-dichlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.483333h; Green chemistry;	96%

: 6287-38-3
3,4-dichlorobenzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(3,4-dichlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.6h; Green chemistry;	96%

: methylbenzenesulfonylmethylisonitrile

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-carbonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In 1,2-dimethoxyethane; ethanol at 0 - 60℃; for 18h;	95%

: 66-77-3
1-naphthaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(naphthalen-1-ylmethylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.516667h; Green chemistry;	95%

: 874-42-0
2,4-dichlorobenzaldeyhde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(2,4-dichlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.583333h; Green chemistry;	95%

: 100-52-7
benzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-benzylidene-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.5h; Reagent/catalyst; Green chemistry;	94%
With sodium hydroxide In water

: 83-38-5
2,6-dichlorobenzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(2,6-dichlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.583333h; Green chemistry;	94%
With sodium hydroxide In water

: 372-09-8
cyanoacetic acid

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 221530-44-5
2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile

Conditions

Conditions	Yield
With piperidine at 100 - 110℃;	93%

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(3,4-dimethoxybenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.666667h; Green chemistry;	93%

: 122-03-2
(4-isopropylbenzaldehyde)

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(4-isopropylbenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.5h; Green chemistry;	91%

: 1489-69-6
Cyclopropanecarboxaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(cyclopropylmethylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.416667h; Green chemistry;	90%

: 109-77-3
malononitrile

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: C14H10N2O

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reagent/catalyst; Solvent;	89.8%

: 2537-48-6
diethyl 1-cyanomethylphosphonate

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 221530-44-5
2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile

Conditions

Conditions	Yield
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Horner-Wadsworth-Emmons olefination; Stage #2: 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one In tetrahydrofuran; mineral oil at 40℃; for 1h; Horner-Wadsworth-Emmons olefination;	89%
Stage #1: diethyl 1-cyanomethylphosphonate With sodium methylate In tetrahydrofuran at 20℃; for 1h; Stage #2: 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one In tetrahydrofuran at 20℃; for 2.25h;	80%
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 25℃; for 1h; Large scale; Stage #2: 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one In tetrahydrofuran; water for 3.5h; Large scale;	5.1 kg
In methanol at 20℃; for 0.25h; Alkaline conditions;
With sodium methylate at 5 - 25℃;

: 2537-48-6
diethyl 1-cyanomethylphosphonate

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 196597-79-2
(E)-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile

Conditions

Conditions	Yield
With sodium methylate In methanol; water; toluene	88%
With sodium methylate In methanol; toluene at 20℃; Wittig Reaction;	88%
With sodium methylate In methanol; toluene at 0℃; for 5h;	84.4%

: 659-28-9
p-trifluoromethoxybenzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(4-[trifluoromethoxy]benzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.333333h; Green chemistry;	86%

: 24964-64-5
3-Cyanobenzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-3-((8-oxo-1,2,6,8-tetrahydro-7H-indeno[5,4-b]furan-7-ylidene)methyl)benzonitrile

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.666667h; Green chemistry;	85%

: 455-19-6
4-Trifluoromethylbenzaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-(4-[trifluoromethyl]benzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.383333h; Green chemistry;	83%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 1093972-05-4
ethyl (2)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylideneacetate

Conditions

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In toluene at 0 - 5℃; for 2h; Stage #2: 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one In toluene at 90 - 100℃; for 15 - 18h;	80%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In toluene; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one In toluene; mineral oil at 90 - 100℃; Inert atmosphere;

: 115262-01-6
[bromo(difluoro)methyl](trimethyl)silane

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 8-fluoro-1,2-dihydronaphtho[2,1-b]furan-9-ol

Conditions

Conditions	Yield
Stage #1: [bromo(difluoro)methyl]-trimethyl-silane; 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one With tetrabutylammomium bromide In toluene at 110℃; for 7h; Sealed tube; Stage #2: With tetrabutyl ammonium fluoride In toluene at 20℃; for 2h;	80%

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: 456-48-4
3-Fluorobenzaldehyde

: (E)-7-(3-fluorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.433333h; Green chemistry;	80%

: 73568-25-9
2-chloro-3-quinoline carboxaldehyde

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: (E)-7-([2-chloroquinolin-3-yl]methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.3h; Green chemistry;	75%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 196597-78-1
1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one

: ethyl (Z)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetate

Conditions

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In toluene at 20℃; for 2h; Cooling with ice; Stage #2: 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one In toluene at 90℃; Cooling with ice;	74%

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Chemical Properties

The Molecular Structure of 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one (CAS NO.196597-78-1):

Empirical Formula: C₁₁H₁₀O₂
Molecular Weight: 174.1959
Nominal Mass: 174 Da
Average Mass: 174.1959 Da
Monoisotopic Mass: 174.06808 Da
Index of Refraction: 1.624
Molar Refractivity: 47.726 cm³
Molar Volume: 135.156 cm³
Surface Tension: 53.251 dyne/cm
Density: 1.289 g/cm³
Flash Point: 165.595 °C
Enthalpy of Vaporization: 57.709 kJ/mol
Boiling Point: 334.156 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Product Categories: Aromatics Compounds;Aromatics;Heterocycles
Appearance: White Solid

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Uses

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one (CAS NO.196597-78-1) can be used as receptor agonist and a therapeutic agent for sleep disorders.

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Specification

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one (CAS NO.196597-78-1) is also called as 1,2,6,7-Tetrahydro-8H-indeno[5,4-β]furan-8-one .

Product Name

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

Synthetic route

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Chemical Properties

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Uses

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Specification

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