Benzarone supplier | CasNO.1477-19-6

Name
Benzarone
EINECS 216-026-2
CAS No. 1477-19-6
Article Data10
CAS DataBase
Density 1.234g/cm³
Solubility
Melting Point 124.3°
Formula C17H14 O3
Boiling Point 473.6°Cat760mmHg
Molecular Weight 266.296
Flash Point 240.2°C
Transport Information
Appearance
Safety Poison by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid and irritating smoke and fumes. See also KETONES.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Ketone,2-ethyl-3-benzofuranyl p-hydroxyphenyl (6CI,7CI,8CI);2-Ethyl-3-(4-hydroxybenzoyl)benzofuran; 2-Ethyl-3-(p-hydroxybenzoyl)benzofuran;2-Ethyl-3-benzofuranyl p-hydroxyphenyl ketone;2-Ethyl-4'-hydroxy-3-benzoylbenzofuran; Benzaron; Benzarone; Fagivil; Fragivil;Fragivix; L 2179-Labaz; L 2197; NSC 82134
PSA 50.44000
LogP 3.93180

Synthetic route

: 3343-80-4
(2-ethylbenzofuran-3-yl)(4-methoxyphenyl)methanone

: 1477-19-6
benzarone

Conditions

Conditions	Yield
With aluminum (III) chloride In chloroform at 80℃; for 0.5h; Temperature; Reagent/catalyst; Large scale;	95%
Stage #1: (2-ethylbenzofuran-3-yl)(4-methoxyphenyl)methanone With sodium thioethylate In N,N-dimethyl-formamide at 125 - 130℃; for 1h; Stage #2: With water; ammonium chloride In N,N-dimethyl-formamide	90%
With sodium thioethylate In N,N-dimethyl-formamide at 125 - 130℃; for 1h;	90%

: 3562-84-3
benzbromarone

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Stage #1: benzbromarone With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; triethylamine In water at 20℃; for 0.0333333h; Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 11.9667h;	86%

: 3131-63-3
2-ethylbenzofuran

: 100-07-2
4-methoxy-benzoyl chloride

: 1477-19-6
benzarone

Conditions

Conditions	Yield
With lewis acid In chloroform at 10 - 30℃; for 4h; Solvent; Temperature;	68.2%

: 3131-63-3
2-ethylbenzofuran

: 1486-50-6
4-(benzyloxy)benzoic acid chloride

A: 101596-43-4
3-benzyl-2-ethylbenzofuran

B: 1477-19-6
benzarone

Conditions

Conditions	Yield
With tin(IV) chloride; benzene

...Expand

: 90908-77-3
(4-acetoxy-phenyl)-(2-ethyl-benzofuran-3-yl)-ketone

: 1477-19-6
benzarone

Conditions

Conditions	Yield
With sodium hydroxide

: 3131-63-3
2-ethylbenzofuran

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tin (IV)-chloride; benzene 2: aq.-ethanolic NaOH-solution View Scheme
Multi-step reaction with 2 steps 1: tin (IV)-chloride; carbon disulfide 2: pyridine hydrochloride View Scheme
Multi-step reaction with 2 steps 1: tin(IV) chloride / carbon disulfide / 5 - 20 °C / Inert atmosphere; Cooling with ice 2: sodium thioethylate / N,N-dimethyl-formamide / 1 h / 125 - 130 °C View Scheme

: 27914-73-4
4-acetoxybenzoyl chloride

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tin (IV)-chloride; benzene 2: aq.-ethanolic NaOH-solution View Scheme

: 100-07-2
4-methoxy-benzoyl chloride

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tin (IV)-chloride; carbon disulfide 2: pyridine hydrochloride View Scheme
Multi-step reaction with 2 steps 1: tin(IV) chloride / carbon disulfide / 5 - 20 °C / Inert atmosphere; Cooling with ice 2: sodium thioethylate / N,N-dimethyl-formamide / 1 h / 125 - 130 °C View Scheme
Multi-step reaction with 2 steps 1: polystyrene-supported aluminum trichloride / dichloromethane / 1 h / 5 - 20 °C / Large scale 2: aluminum (III) chloride / chloroform / 0.5 h / 80 °C / Large scale View Scheme

: 1646-26-0
1-(benzo[b]furan-2-yl)ethanone

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrazine / water; diethylene glycol / 120 - 190 °C 1.2: 6 h / 120 - 130 °C 2.1: tin(IV) chloride / carbon disulfide / 5 - 20 °C / Inert atmosphere; Cooling with ice 3.1: sodium thioethylate / N,N-dimethyl-formamide / 1 h / 125 - 130 °C View Scheme
Multi-step reaction with 3 steps 1.1: hydrazine / water; diethylene glycol / 120 - 190 °C 1.2: 6 h / 120 - 130 °C 2.1: carbon disulfide / 0.5 h / Inert atmosphere; Cooling with ice 2.2: 6 h / 20 °C / Cooling with ice 3.1: sodium thioethylate / N,N-dimethyl-formamide / 1 h / 125 - 130 °C View Scheme

: 90-02-8
salicylaldehyde

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 6 h / Reflux 2.1: hydrazine / water; diethylene glycol / 120 - 190 °C 2.2: 6 h / 120 - 130 °C 3.1: tin(IV) chloride / carbon disulfide / 5 - 20 °C / Inert atmosphere; Cooling with ice 4.1: sodium thioethylate / N,N-dimethyl-formamide / 1 h / 125 - 130 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / ethanol / 2 h / Reflux 1.2: 2 h / Reflux 1.3: 0.17 h / Reflux 2.1: tin(IV) chloride / chloroform / 20 °C / Cooling with ice 3.1: ethanethiol; sodium hydride / N,N-dimethyl-formamide / 3 h / 110 °C View Scheme

: 100-52-7
benzaldehyde

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 6 h / Reflux 2.1: hydrazine / water; diethylene glycol / 120 - 190 °C 2.2: 6 h / 120 - 130 °C 3.1: carbon disulfide / 0.5 h / Inert atmosphere; Cooling with ice 3.2: 6 h / 20 °C / Cooling with ice 4.1: sodium thioethylate / N,N-dimethyl-formamide / 1 h / 125 - 130 °C View Scheme

: 54103-36-5
1-(4-methoxyphenyl)-1,3-pentanedione

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C 2: boron tribromide / dichloromethane / 10 h View Scheme

: 100-06-1
1-(4-methoxyphenyl)ethanone

: 1477-19-6
benzarone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / mineral oil; tetrahydrofuran / Reflux 2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C 3: boron tribromide / dichloromethane / 10 h View Scheme

: 1477-19-6
benzarone

: 3562-84-3
benzbromarone

Conditions

Conditions	Yield
With bromine; acetic acid In water at 20℃; for 2h;	98%
With N-Bromosuccinimide In dichloromethane; N,N-dimethyl-formamide at -10 - 20℃; for 17h;	82%
With bromine; acetic acid for 0.25h; Product distribution / selectivity;	35%

: 1477-19-6
benzarone

: 540-51-2
2-bromoethanol

: 2-ethyl-3-[4-(2-hydroxy-ethoxy)-benzoyl]-benzofuran

Conditions

Conditions	Yield
With sodium hydroxide; potassium carbonate In N,N-dimethyl-formamide; Petroleum ether	97.4%

: 1477-19-6
benzarone

: 82699-09-0
Natriumbenzaronsulfat

Conditions

Conditions	Yield
With aminosulfonic acid; sodium carbonate 1.) pyridine, 90 deg C, 2 h, 2.) H2O;	74%

: 1477-19-6
benzarone

: 68-90-6
benziodarone

Conditions

Conditions	Yield
With iodine; silver nitrate In methanol at 20℃; for 3h;	46.2%

: 1477-19-6
benzarone

: 51073-13-3
(3,5-dibromo-4-methoxy-phenyl)-(2-ethyl-benzofuran-3-yl)-methanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous acetic acid; bromine 2: ethanolic KOH-solution View Scheme
Multi-step reaction with 2 steps 1.1: bromine; acetic acid / 0.25 h 2.1: potassium carbonate / tetrahydrofuran / 0.17 h 2.2: 16 h / 40 °C View Scheme

: 1477-19-6
benzarone

A: 68-90-6
benziodarone

B: 3562-84-3
benzbromarone

aluminum chloride anhydride powder: aluminum chloride anhydride powder

: 1477-19-6
benzarone

: 107-14-2
chloroacetonitrile

: 91627-69-9
5-[4-(2-ethyl-3-benzofuroyl)phenoxymethyl]tetrazole

Conditions

Conditions	Yield
With hydrogenchloride; NaH In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide

...Expand

: 1477-19-6
benzarone

: 106-89-8
epichlorohydrin

A 2-ethyl-3-[4'-(2-hydroxy-3-isopropylamino)propoxybenzoyl]benzofuran: 2-ethyl-3-[4'-(2-hydroxy-3-isopropylamino)propoxybenzoyl]benzofuran

B: 61085-19-6
2-ethyl-3-[4'-(2,3-epoxy)propoxybenzoyl]benzofuran

...Expand

: 1477-19-6
benzarone

A: 5-(2-ethylbenzofuran-3-carbonyl)-2-hydroxy-3-iodobenzonitrile

B: 5-(2-ethylbenzofuran-3-carbonyl)-2-hydroxyisophthalonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: silver nitrate; iodine / methanol / 3 h / 20 °C 2: N,N-dimethyl-formamide / 5 h / 100 °C View Scheme

: 1477-19-6
benzarone

: 5-(2-ethylbenzofuran-3-carbonyl)-2-hydroxybenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: silver nitrate; iodine / methanol / 3 h / 20 °C 2: N,N-dimethyl-formamide / 5 h / 100 °C 3: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr View Scheme

: 1477-19-6
benzarone

: 3-bromo-5-(2-ethylbenzofuran-3-carbonyl)-2-hydroxybenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: silver nitrate; iodine / methanol / 3 h / 20 °C 2: N,N-dimethyl-formamide / 5 h / 100 °C 3: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr 4: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C View Scheme

: 1477-19-6
benzarone

: acetic acid 4-(2-ethylbenzofuran-3-carbonyl)-2,6-diiodophenyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: silver nitrate; iodine / methanol / 3 h / 20 °C 2: dmap; pyridine / 2 h / 20 °C View Scheme

: 1477-19-6
benzarone

: acetic acid 4-(2-ethylbenzofuran-3-carbonyl)-2-iodo-6-(trifluoromethyl)phenyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: silver nitrate; iodine / methanol / 3 h / 20 °C 2: dmap; pyridine / 2 h / 20 °C 3: copper(l) iodide / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere View Scheme

: 1477-19-6
benzarone

: (2-ethylbenzofuran-3-yl)[4-hydroxy-3-iodo-5-(trifluoromethyl)phenyl]methanone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: silver nitrate; iodine / methanol / 3 h / 20 °C 2: dmap; pyridine / 2 h / 20 °C 3: copper(l) iodide / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere 4: potassium carbonate / methanol / 2 h / 20 °C View Scheme

: 1477-19-6
benzarone

: 5-(2-ethylbenzofuran-3-carbonyl)-2-hydroxy-3-(trifluoromethyl)benzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: silver nitrate; iodine / methanol / 3 h / 20 °C 2: dmap; pyridine / 2 h / 20 °C 3: copper(l) iodide / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere 4: potassium carbonate / methanol / 2 h / 20 °C 5: N,N-dimethyl-formamide / 100 °C View Scheme

Benzarone Chemical Properties

Molecular Structure of Benzarone (CAS NO. 1477-19-6):

EINECS: 216-026-2
IUPAC Name: (2-Ethyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone
Molecular Formula: C₁₇H₁₄O₃
Molecular Weight: 266.291260 g/mol
XLogP3: 4.3
H-Bond Donor: 1
H-Bond Acceptor: 3
Canonical SMILES: CCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC=C(C=C3)O
InChI: InChI=1S/C17H14O3/c1-2-14-16(13-5-3-4-6-15(13)20-14)17(19)11-7-9-12(18)10-8-11/h3-10,18H,2H2,1H3
InChIKey: RFRXIWQYSOIBDI-UHFFFAOYSA-N
Index of Refraction: 1.638
Molar Refractivity: 77.61 cm³
Molar Volume: 215.7 cm³
Surface Tension: 50.9 dyne/cm
Density: 1.234 g/cm³
Flash Point: 240.2 °C
Enthalpy of Vaporization: 76.49 kJ/mol
Boiling Point: 473.6 °C at 760 mmHg
Vapour Pressure: 1.36E-09 mmHg at 25 °C
Water Solubility of Benzarone (CAS NO. 1477-19-6): 17.07 mg/L at 25 °C

Benzarone Toxicity Data With Reference

ipr-mus LD50:200 mg/kg

AIPTAK Archives Internationales de Pharmacodynamie et de Therapie, 154 (1965),94.

Benzarone Consensus Reports

Reported in EPA TSCA Inventory.

Benzarone Safety Profile

Poison by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid and irritating smoke and fumes. See also KETONES.

Benzarone Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid

Benzarone Specification

Benzarone with cas registry number of 1477-19-6 is also known as 2-Ethyl-3-(4-hydroxybenzoyl)benzofuran ; 2-Ethyl-3-(p-hydroxybenzoyl)benzofuran ; 2-Ethyl-3-benzofuranyl p-hydroxyphenyl ketone ; 2-Ethyl-3-(4'-hydroxybenzoyl)benzofuran ; 2-Ethyl-4'-hydroxy-3-benzoylbenzofuran ; 5-18-02-00334 (Beilstein Handbook Reference) ; Benzarona ; Benzarona [INN-Spanish] ; Benzarone [INN:DCF] ; Benzarone ; Benzaronum ; Benzaronum [INN-Latin] ; Benzofuran, (2-ethyl-3-(4'-hydroxybenzoyl)) ; Ethyl-2 (hydroxy-4 benzoyl)-3 benzofuranne ; Ethyl-2 (hydroxy-4 benzoyl)-3 benzofuranne [French] ; Fragivix ; L 2197 ; L 2197-Labaz ; Methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)- ; NSC 82134 ; UNII-23ZW4BG89C ; Vasoc ; Venagil ; Ketone, 2-ethyl-3-benzofuranyl p-hydroxyphenyl .

Product Name

Benzarone

Synthetic route

Benzarone Chemical Properties

Benzarone Toxicity Data With Reference

Benzarone Consensus Reports

Benzarone Safety Profile

Benzarone Standards and Recommendations

Benzarone Specification

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