ChemicalBook > Product Catalog > Analytical Chemistry > Standard > Pharmaceutical Impurity Reference Standards > Benzarone
Benzarone Chemical Properties
- Melting point:124.3°
- Boiling point:369.5°C (rough estimate)
- Density 1.1601 (rough estimate)
- refractive index 1.5490 (estimate)
- form neat
- EPA Substance Registry SystemMethanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)- (1477-19-6)
- ToxicityLD50 ipr-mus: 200 mg/kg AIPTAK 154,94,65
Benzarone Usage And Synthesis
- Chemical PropertiesPale Yellow Solid
- Manufacturing ProcessThe process of preparation of the 2-ethyl-3-(4'-hydroxybenzoyl)benzofurane includes the next steps:
1. To 1 mol of potassium hydroxide in absolute ethanol is added 1 mole of
salicylic aldehyde. The mixture is brought to boiling point in water bath until
the potassium salt formed is dissolved. One mole of coloroacetone is gradually
added and the solution boiled in a reflux condenser for 2 hours. On cooling
the potassium chloride precipitate is separated off by filtration. The residue is
distilled to give 2-acetyl-1-benzofurane, BP: 135°C/15 mm Hg.
2. It was reduced by hydrazine hydrate in an alkaline medium (by process of Hyuang-Minlon, J.A.C.S., 1946, 68, 2487) to give 2-ethyl-1-benzofurane BP: 211°-212°C.
3. 2-Ethyl-1-benzofurane is condensed with 2-metoxybenzoyl chloride in the presence of tin tetrachloride (according to the process described by Bisagni, J.C.S., 1955, 3694). Thus 2-ethyl-3-(4-methoxybenzoyl)-1-benzofyrane is obtained. BP: 226°C/15 mm Hg.
4. 1 part of 2-ethyl-3-(4-methoxybenzoyl)-1-benzofyrane is mixed with 2 parts of pyridine hydrochloride and heated at an oil bath at 210°C in N2 current for 1 hour. On cooling 10 parts of 0.5 N HCl are added. A water layer is mixed with 20 parts of 1% NaOH. The alkaline layer is separated, acidified with diluted HCl. The dropped precipitate (2-ethyl-3-(4'-hydroxybenzoyl) benzofurane) is recrystallized from acetic acid. MP: 124.3°C.
- brand nameBenzarin;Fragivix (r) forte;Vasco.
- Therapeutic FunctionAntihemorrhagic
- World Health Organization (WHO)Benzarone is given by mouth and applied topically for treatment of various vascular peripheral disorders.The decision to suspend the marketing authorization results from several reports of toxic hepatitis, including one fatal case from within Germany. The product remains registered in Italy and France.
- Safety ProfilePoison 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 Diethyl ether Ethanol Hydroxyphenyl 4-Methoxyphenol 2-Ethoxyethanol Ethylparaben 1-Hydroxyethylidene-1,1-diphosphonic acid Ethyl propionate Methylparaben Triclosan ISOXADIFEN-ETHYL Ethyl formate 4-Ethyl-5-fluoro-6-hydroxypyrimidine 4-Hydroxy-D-(-)-2-phenylglycine Ethyl acetate 4-Hydroxybenzoic acid Trinexapac-ethyl
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