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39552-01-7

39552-01-7 Structure

39552-01-7 Structure
IdentificationBack Directory
[Name]

Befunolol
[CAS]

39552-01-7
[Synonyms]

Befunolol
2-acetyl-7-(2-hyroxy-3-isopropylaminopropoxy)benzofuran
2-Acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran
(-)-2-Acetyl-7-[(S)-2-hydroxy-3-isopropylaminopropoxy]benzofuran
(+)-2-Acetyl-7-[(R)-2-hydroxy-3-isopropylaminopropoxy]benzofuran
7-(2-hydroxy-3-(isopropylamino)propoxy)-2-benzofuranyl methyl ketone
7-[2-Hydroxy-3-(iso-propylamino)propoxy]-2-benzofuranyl methyl ketone
ketone, 7-(2-hydroxy-3-(isopropylamino)propoxy)-2-benzofuranyl methyl
1-(7-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2-benzofuranyl)-ethanon
1-(7-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-2-benzofuranyl)ethanone
1-[7-[2-Hydroxy-3-[(1-methylethyl)-amino]propoxy]-2-benzofuranyl]ethanone
Ethanone, 1-[7-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2-benzofuranyl]-
[Molecular Formula]

C16H21NO4
[MDL Number]

MFCD00864594
[MOL File]

39552-01-7.mol
[Molecular Weight]

291.34
Chemical PropertiesBack Directory
[Melting point ]

115°
[Boiling point ]

433.35°C (rough estimate)
[density ]

1.1049 (rough estimate)
[refractive index ]

1.5500 (estimate)
[storage temp. ]

Hygroscopic, -20°C Freezer, Under inert atmosphere
[solubility ]

Chloroform (Slightly), DMSO (Slightly, Heated)
[form ]

Solid
[color ]

White to Off-White
[Contact allergens]

Befunolol was implicated in allergic contact dermatitis due to beta-blocker agents in eye-drops. Crosssensitivity has been described with levobunolol.
[CAS DataBase Reference]

39552-01-7
Hazard InformationBack Directory
[Uses]

Befunolol is a β-adrenergic blocker with an intrinsic sympathomimetic action. But it can work as a β-adrenergic partial agonist in isolated organs.
[Chemical Properties]

Crystallizes. Melting point 115°C. Benfurol hydrochloride (C16H21NO4·HCl), melting point 163°C.
[Originator]

Bentos,Kakenyaku Kako,Japan,1983
[Definition]

ChEBI:Befunolol is a member of benzofurans.
[Manufacturing Process]

To 8.8 g of 2-acetyl-7-hydroxybenzofuran were added 80 ml of epichlorohydrin and 0.2 g of piperidine hydrochloride and the mixture was heated at 105°C for 3 hours. After the reaction, the excess of epichlorohydrin was evaporated and the resultant was distilled under reduced pressure to give 9.3 g of 2-acetyl-7-(2,3-epoxypropoxy)benzofuranhaving a boiling point of 175° to 176°C/0.7 mm Hg. 6 g of the product was dissolved in 30 ml of ethanol and to the solution was added 10 ml of isopropylamine. After refluxing the mixture for 40 minutes, the solvent was evaporated from the reaction mixture. The resulting residue was recrystallized from cyclohexane-acetone to give 6 g of 2-acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran having a melting point of 115°C.
[Therapeutic Function]

Beta-adrenergic blocker
[storage]

Store at -20°C
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Epichlorohydrin-->Cyclohexane-->Isopropylamine-->Benzofuran-->Piperidine hydrochloride-->Propoxybenzene-->2-ACETYL-7-HYDROXYBENZOFURAN
Safety DataBack Directory
[Toxicity]

LD50 in mice: 100-105 mg/kg i.v. (Ito)
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