5-Benzofuranol supplier | CasNO.13196-10-6

Name
5-Benzofuranol
EINECS
CAS No. 13196-10-6
Article Data37
CAS DataBase
Density 1.28g/cm³
Solubility
Melting Point 186-187℃
Formula C₈H₆O₂
Boiling Point 247.139 °C at 760 mmHg
Molecular Weight 134.134
Flash Point 103.267 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-BENZOFURANOL;5-Hydroxybenzofuran;Benzofuran-5-ol;5-Hydroxybenzo[b]furan;Benzo[b]furan-5-ol;1-benzofuran-5-ol
PSA 33.37000
LogP 2.13840

Synthetic route

: 13391-28-1
5-methoxybenzofuran

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃; for 2h; Inert atmosphere;	89%
With boron tribromide In dichloromethane at -78 - 20℃; for 3h; Inert atmosphere; regioselective reaction;	85%
With boron tribromide-dimethyl sulfide complex In chlorobenzene at 130℃; for 12h;	80%

: 23145-07-5
5-bromobenzofuran

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;	66%

: 331834-13-0
2,3-dihydro-1-benzofuran-5-ylboronic acid

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
With water; triethylamine In acetonitrile at 20℃; for 36h; Irradiation;	56%
With Oxone; potassium phosphate; 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In water at 70℃; for 1h; chemoselective reaction;

: 3673-68-5
2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol

A: 106-44-5
p-cresol

B: 13196-10-6
benzofuran-5-ol

C: 123-07-9
4-Ethylphenol

D: 501-94-0
p-hydroxyphenethyl alcohol

E: 1240059-73-7
1-[4-(2-hydroxyethyl)phenoxy]-2-(4'-hydroxyphenyl)ethane

F: 501123-58-6
di[2-(4-hydroxyphenyl)]ethyl ether

G: C24H34O3

H: 117516-54-8
6-tert-butyl-5-hydroxybenzofuran

I: 108-95-2
phenol

Conditions

Conditions	Yield
at 295 - 298℃; for 22h; Inert atmosphere;	A n/a B n/a C n/a D 55% E n/a F 40 g G n/a H n/a I n/a

...Expand

: 609-39-2
2-nitrofuran

: 54125-02-9
danishefsky's diene

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
In benzene at 120℃; for 72h; Diels-Alder reaction;	50%

: 152560-12-8
(+)-(3S)-3-hydroxy-2,3-dihydrobenzofuran

A: 13196-10-6
benzofuran-5-ol

B: 141977-89-1
(+)-(4R,5S)-cis-4,5-dihydroxy-4,5-dihydrobenzofuran

C: (+)-(3S)-3,5-dihydroxy-2,3-dihydrobenzofuran

Conditions

Conditions	Yield
for 22h; Pseudomonas putida UV4;	A 13% B 4% C 22%

...Expand

: 496-16-2
2,3-Dihydrobenzofuran

A: 13196-10-6
benzofuran-5-ol

B: 152560-12-8
(+)-(3S)-3-hydroxy-2,3-dihydrobenzofuran

C: 152560-17-3
(-)-(3R)-3-hydroxy-2,3-dihydrobenzofuran

Conditions

Conditions	Yield
Pseudomonas putida UV4; Yields of byproduct given;	A 9% B n/a C n/a
Pseudomonas putida UV4; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 5380-80-3
(-/+)-3-hydroxy-2,3-dihydrobenzofuran

A: 13196-10-6
benzofuran-5-ol

B: 141852-40-6, 141977-89-1
(-)-(4S,5R)-cis-4,5-dihydroxy-4,5-dihydrobenzofuran

C: 141977-89-1
(+)-(4R,5S)-cis-4,5-dihydroxy-4,5-dihydrobenzofuran

D: (+)-(3S)-3,5-dihydroxy-2,3-dihydrobenzofuran

Conditions

Conditions	Yield
for 20h; Pseudomonas putida UV4; Yield given. Further byproducts given. Title compound not separated from byproducts;	A 4% B n/a C n/a D n/a

...Expand

: 5380-80-3
(-/+)-3-hydroxy-2,3-dihydrobenzofuran

A: 13196-10-6
benzofuran-5-ol

B: 141977-89-1
(+)-(4R,5S)-cis-4,5-dihydroxy-4,5-dihydrobenzofuran

C: (+)-(3S)-3,5-dihydroxy-2,3-dihydrobenzofuran

D: (-)-(3S)-3,5-dihydroxy-2,3-dihydrobenzofuran

Conditions

Conditions	Yield
for 20h; Pseudomonas putida UV4; Further byproducts given. Yields of byproduct given;	A 4% B n/a C n/a D n/a
for 20h; Pseudomonas putida UV4; Yield given. Further byproducts given. Title compound not separated from byproducts;	A 4% B n/a C n/a D n/a

...Expand

: 152560-17-3
(-)-(3R)-3-hydroxy-2,3-dihydrobenzofuran

A: 13196-10-6
benzofuran-5-ol

B: (-)-(3S)-3,5-dihydroxy-2,3-dihydrobenzofuran

Conditions

Conditions	Yield
for 22h; Pseudomonas putida UV4;	A 2% B 3%

: 69034-13-5
p-methoxyphenoxyacetaldehyde diethyl acetal

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / poliphosphoric acid / benzene / 2 h / 100 °C 2: 80 percent / BBr3*SMe2 / chlorobenzene / 12 h / 130 °C View Scheme
Multi-step reaction with 2 steps 1.1: Amberlyst 15 / toluene / 6 h / Reflux 2.1: boron tribromide / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 2.2: 0.25 h / -20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: Amberlyst 15 / toluene / 6 h / Reflux 2.1: boron tribromide / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 2.2: 0.25 h / -20 °C / Inert atmosphere View Scheme

: 150-76-5
4-methoxy-phenol

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / potassium carbonate / dimethylformamide / 3 h / Heating 2: 35 percent / poliphosphoric acid / benzene / 2 h / 100 °C 3: 80 percent / BBr3*SMe2 / chlorobenzene / 12 h / 130 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 0.33 h / 20 °C 1.2: 4 h / 120 °C 2.1: Amberlyst 15 / toluene / 6 h / Reflux 3.1: boron tribromide / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 3.2: 0.25 h / -20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 0.33 h / 20 °C 1.2: 4 h / 120 °C 2.1: Amberlyst 15 / toluene / 6 h / Reflux 3.1: boron tribromide / dichloromethane / 2 h / -20 - 20 °C / Inert atmosphere 3.2: 0.25 h / -20 °C / Inert atmosphere View Scheme

: 496-16-2
2,3-Dihydrobenzofuran

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Pseudomonas putida UV4 2: 13 percent / 22 h / Pseudomonas putida UV4 View Scheme
Multi-step reaction with 2 steps 1: Pseudomonas putida UV4 2: 2 percent / 22 h / Pseudomonas putida UV4 View Scheme

: 5380-80-3
(-/+)-3-hydroxy-2,3-dihydrobenzofuran

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 13 percent / 22 h / Pseudomonas putida UV4 View Scheme
Multi-step reaction with 2 steps 2: 2 percent / 22 h / Pseudomonas putida UV4 View Scheme

: 150-76-5
4-methoxy-phenol

: 2032-35-1
Bromoacetaldehyde diethyl acetal

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Stage #1: 4-methoxy-phenol; Bromoacetaldehyde diethyl acetal With potassium hydroxide Stage #2:

: 75717-53-2
2-chloro-1-(2-hydroxy-5-methoxyphenyl)ethan-1-one

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium acetate / methanol / 1.5 h / Reflux 2: sodium tetrahydroborate; methanol / 0 - 20 °C 3: trifluoroacetic acid / acetonitrile 4: boron tribromide / dichloromethane / 2 h / -60 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sodium acetate / methanol / 1.5 h / Reflux 2: methanol; sodium tetrahydroborate / 0 - 20 °C 3: trifluoroacetic acid / acetonitrile 4: boron tribromide / dichloromethane / 2 h / -60 - 0 °C / Inert atmosphere View Scheme

: 39581-55-0
5-methoxy-benzofuran-3-one

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol / 0 - 20 °C 2: trifluoroacetic acid / acetonitrile 3: boron tribromide / dichloromethane / 2 h / -60 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: methanol; sodium tetrahydroborate / 0 - 20 °C 2: trifluoroacetic acid / acetonitrile 3: boron tribromide / dichloromethane / 2 h / -60 - 0 °C / Inert atmosphere View Scheme

: 33320-42-2
5-methoxy-2,3-dihydro-benzofuran-3-ol

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid / acetonitrile 2: boron tribromide / dichloromethane / 2 h / -60 - 0 °C / Inert atmosphere View Scheme

: 51343-96-5
2-[4-(benzyloxy)phenoxy]acetaldehyde diethyl acetal

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid / benzene / 2 h / 23 °C / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 23 °C View Scheme

: 92496-27-0
5-(benzyloxy)benzofuran

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 23℃; for 4h;

: C13H12BNO5

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
Stage #1: C13H12BNO5 With potassium phosphate; 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In water at 80℃; for 0.25h; Stage #2: With Oxone In water at 70℃; for 1h; chemoselective reaction;

: C12H15NO3

: 13196-10-6
benzofuran-5-ol

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water for 2h; Reflux;

: 13196-10-6
benzofuran-5-ol

: 3-(bromomethyl)pyridine hydrobromide

: 3-[(1-benzofuran-5-yloxy)methyl]pyridine

Conditions

Conditions	Yield
Stage #1: benzofuran-5-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Stage #2: 3-(bromomethyl)pyridine hydrobromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 18h;	99%

: 13196-10-6
benzofuran-5-ol

: 3188-13-4
ethyl chloromethyl ether

: 1211333-08-2
5-(ethoxymethoxy)benzofuran

Conditions

Conditions	Yield
Stage #1: benzofuran-5-ol With sodium ethanolate In ethanol; ethyl acetate at -7.1℃; for 0.0833333h; Stage #2: ethyl chloromethyl ether In ethanol; ethyl acetate at -14.5 - 20℃;	97%
Stage #1: benzofuran-5-ol With sodium hydride In N,N-dimethyl-formamide; oil at 0 - 20℃; Stage #2: ethyl chloromethyl ether In N,N-dimethyl-formamide; oil at 0 - 20℃;

: 13196-10-6
benzofuran-5-ol

: 762-49-2
2-fluoroethyl bromide

: 5-(2-fluoroethoxy)-1-benzofuran

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 99h;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 99h;	93%

: 13196-10-6
benzofuran-5-ol

: 107-30-2
chloromethyl methyl ether

: 5-(methoxymethoxy)-1-benzofuran

Conditions

Conditions	Yield
Stage #1: benzofuran-5-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3.5h; Inert atmosphere;	89%
Stage #1: benzofuran-5-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3.5h;	89%
Stage #1: benzofuran-5-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.58333h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	89%

: 13196-10-6
benzofuran-5-ol

: 37831-62-2
ethyl 4-chloronicotinate

: 1618131-46-6
ethyl 4-(benzofuran-5-yloxy)nicotinate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 110℃;	86%

: 13196-10-6
benzofuran-5-ol

: 3282-30-2
pivaloyl chloride

: benzofuran-5-yl pivalate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Sealed tube;	86%

: 75-77-4
chloro-trimethyl-silane

: 13196-10-6
benzofuran-5-ol

: (benzofuran-5-yloxy)trimethyl silane

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -5 - 40℃; Large scale;	81.4%
Stage #1: benzofuran-5-ol With triethylamine In dichloromethane at 40℃; Large scale; Stage #2: chloro-trimethyl-silane In dichloromethane at -5℃; for 1h; Large scale;	81.4%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	290 mg

: 13196-10-6
benzofuran-5-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: (benzofuran-5-yloxy)(tert-butyl)dimethylsilane

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;	81%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 20h;	81%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 20h;	81%

: 13196-10-6
benzofuran-5-ol

: 115314-14-2, 115314-17-5
(R)-glycidyl nosylate

: (R)-5-(oxiran-2-ylmethoxy)benzofuran

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;	78%

: 13196-10-6
benzofuran-5-ol

: 40432-23-3
4-bromo-5-hydroxybenzofuran

Conditions

Conditions	Yield
With N-Bromosuccinimide; diisopropylamine In dichloromethane for 16h; Inert atmosphere; Reflux;	70%
With bromine In methanol at -30℃; for 1.5h;
With bromine In methanol at -78℃;	2.3 g

: 13196-10-6
benzofuran-5-ol

: 145100-51-2
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

: benzofuran-5-yl triflate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	68%

: 13196-10-6
benzofuran-5-ol

: 3637-61-4
1-amino-cyclopentanemethanol

: 939050-91-6
5-(cyclopentylmethoxy)benzofuran

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h;	65%

: 13196-10-6
benzofuran-5-ol

: 7462-74-0
2-bromo-2-methylpropanamide

: 909398-09-0
2-(benzofuran-5-yloxy)-2-methyl-propionamide

Conditions

Conditions	Yield
With sodium hydride In 1,4-dioxane at 100℃; for 6h;	60%

: 13196-10-6
benzofuran-5-ol

: 15761-39-4
1-(tert-butoxycarbonyl)-L-proline

: 2-(benzofuran-5-yl)-1-(tert-butyl)(S)-pyrrolidine-1,2-dicarboxylate

Conditions

Conditions	Yield
With nickel(II) bromide dimethoxyethane; 4,4'-Dimethoxy-2,2'-bipyridin; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl acetamide at 20℃; for 10h; Inert atmosphere; Glovebox; Electrolysis;	60%

: 13196-10-6
benzofuran-5-ol

: 51359-78-5
4-(bromomethyl)benzaldehyde

: 4-((benzofuran-5-oxy)methyl)benzaldehyde

Conditions

Conditions	Yield
Stage #1: benzofuran-5-ol With caesium carbonate In ethanol at 20℃; for 1h; Stage #2: 4-(bromomethyl)benzaldehyde With potassium iodide In ethanol at 80℃; for 4h;	55.38%
Stage #1: benzofuran-5-ol With caesium carbonate In ethanol at 20℃; for 1h; Williamson Ether Synthesis; Stage #2: 4-(bromomethyl)benzaldehyde With potassium iodide In ethanol for 4h; Williamson Ether Synthesis; Reflux;

: 13196-10-6
benzofuran-5-ol

: 108-90-7
chlorobenzene

: 7182-29-8
5-hydroxy-2-phenylbenzofuran

Conditions

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; diethyl ether at -50℃; for 14h; Sealed tube; Inert atmosphere;	53%

: 13196-10-6
benzofuran-5-ol

: 40492-52-2
2,3-dihydrobenzofuran-5-ol

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol under 2585.81 Torr; for 19h;	51%

: 13196-10-6
benzofuran-5-ol

: 87925-17-5
nitro-4 hydroxy-5 benzofuranne

Conditions

Conditions	Yield
With Nitrogen dioxide 1.) benzene, 0 deg C, 2 h; 2.) 20 deg C, ethanol;	50%

: 13196-10-6
benzofuran-5-ol

: 82072-23-9
3-(bromomethyl)benzaldehyde

: 3-((benzofuran-5-oxy)methyl)benzaldehyde

Conditions

Conditions	Yield
Stage #1: benzofuran-5-ol With caesium carbonate In ethanol at 20℃; for 1h; Stage #2: 3-(bromomethyl)benzaldehyde With potassium iodide In ethanol at 80℃; for 4h;	50%
Stage #1: benzofuran-5-ol With caesium carbonate In ethanol at 20℃; for 1h; Williamson Ether Synthesis; Stage #2: 3-(bromomethyl)benzaldehyde With potassium iodide In ethanol for 4h; Williamson Ether Synthesis; Reflux;

: 13196-10-6
benzofuran-5-ol

: 4584-46-7
(2-chloroethyl)dimethylamine hydrochloride

: [2-(1-benzofuran-5-yloxy)ethyl]dimethylamine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; for 21h;	44%

: 13196-10-6
benzofuran-5-ol

: 6780-49-0
Ethyl N-phenylformimidate

: 5-Hydroxy-4-(N-phenyliminomethyl)benzofuran

Conditions

Conditions	Yield
for 2h; Heating;	29%

5-Benzofuranol Specification

The 5-Benzofuranol, with CAS registry number 13196-10-6, has the systematic name of 1-benzofuran-5-ol. Besides this, it is also called benzofuran-5-ol. And the chemical formula of this chemical is C₈H₆O₂.

Physical properties of 5-Benzofuranol: (1)ACD/LogP: 2.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 17; (6)ACD/BCF (pH 7.4): 17; (7)ACD/KOC (pH 5.5): 268; (8)ACD/KOC (pH 7.4): 265; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 33.37 Å²; (13)Index of Refraction: 1.651; (14)Molar Refractivity: 38.277 cm³; (15)Molar Volume: 104.774 cm³; (16)Polarizability: 15.174×10^-24cm³; (17)Surface Tension: 51.079 dyne/cm; (18)Density: 1.28 g/cm³; (19)Flash Point: 103.267 °C; (20)Enthalpy of Vaporization: 50.389 kJ/mol; (21)Boiling Point: 247.139 °C at 760 mmHg; (22)Vapour Pressure: 0.017 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc2cc1c(occ1)cc2
(2)InChI: InChI=1/C8H6O2/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,9H
(3)InChIKey: IZFOPMSVNDORMZ-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C8H6O2/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,9H
(5)Std. InChIKey: IZFOPMSVNDORMZ-UHFFFAOYSA-N

Product Name

5-Benzofuranol

Synthetic route

5-Benzofuranol Specification

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