Introduction：Basic information about Acebutolol hydrochloride CAS 34381-68-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Acebutolol hydrochloride Basic information
| Product Name: | Acebutolol hydrochloride |
| Synonyms: | ACEBUTOLOL HCL;ACEBUTOLOL HYDROCHLORIDE;N-[3-ACETYL-4-(2-HYDROXY-3-[ISOPROPYLAMINO]PROPOXY)PHENYL]-BUTANAMIDE HYDROCHLORIDE;n-[3-acetyl-4-[2-hydroxy-3-[(isopropyl)amino]propoxy]phenyl]butyramide hydrochloride;3’-Acetyl-4’-(2-Hydroxy-3-(Isopropylamino)Prop;Acebutolol hydrochloride,N-(3-Acetyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl)butanamide;Acebutolol Hydrochloride (125 mg);Acebutolol Hydrochloride iMpurity A |
| CAS: | 34381-68-5 |
| MF: | C18H29ClN2O4 |
| MW: | 372.89 |
| EINECS: | 251-980-3 |
| Product Categories: | AVODART;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 34381-68-5.mol |
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Acebutolol hydrochloride Chemical Properties
| Melting point | 141-1430C |
| storage temp. | 2-8°C |
| solubility | Freely soluble in water and in ethanol (96 per cent), very slightly soluble in acetone and in methylene chloride. |
| form | Solid |
| color | White to Pale Yellow |
| InChI | InChI=1S/C18H28N2O4.ClH/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3;/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23);1H |
| InChIKey | KTUFKADDDORSSI-UHFFFAOYSA-N |
| SMILES | C1(OCC(O)CNC(C)C)C=CC(NC(=O)CCC)=CC=1C(=O)C.Cl |
| CAS DataBase Reference | 34381-68-5(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20/21/22 |
| Safety Statements | 36 |
| WGK Germany | 3 |
| RTECS | ES5235000 |
| HS Code | 2924296000 |
| Hazardous Substances Data | 34381-68-5(Hazardous Substances Data) |
| Toxicity | LD50 orl-rat: 6620 mg/kg OYYAA2 20,883,80 |
Acebutolol hydrochloride Usage And Synthesis
| Chemical Properties | Off-White Powder |
| Originator | Sectral ,May and Baker ,UK ,1975 |
| Uses | Cardioselective ?adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II) |
| Uses | Cardioselective β-adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II). |
| Uses | 5-alpha-reductase inhibitor |
| Definition | ChEBI: The hydrochloride salt of acebutolol, prepared using equimolar amounts of acebutolol and hydrogen chloride. |
| Manufacturing Process | Crude 5'-butyramido-2'-(2,3-epoxypropoxy)acetophenone (16 g),isopropylamine (20 g) and ethanol (100 ml) were heated together underreflux for 4 hours. The reaction mixture was concentrated under reducedpressure and the residual oil was dissolved in N hydrochloric acid. The acidsolution was extracted with ethyl acetate, the ethyl acetate layers beingdiscarded. The acidic solution was brought to pH 11 with 2 N aqueous sodiumhydroxide solution and then extracted with chloroform. The dried chloroformextracts were concentrated under reduced pressure to give an oil which wascrystallized from a mixture of ethanol and diethyl ether to give 5'-butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenone (3 g), MP 119-123°C.
Crude 5'-butyramido-2'-(2,3-epoxypropoxy)acetophenone used as startingmaterial was prepared as follows: p-butyramidophenol (58 g; preparedaccording to Fierz-David and Kuster, Helv. Chim. Acta 1939,2282), acetylchloride (25.4 g) and benzene (500 ml) were heated together under refluxuntil a solution formed (12 hours). This solution was cooled and treated withwater. The benzene layer was separated and the aqueous layer was againextracted with benzene.
The combined benzene extracts were dried and evaporated to dryness underreduced pressure to give p-butyramidophenyl acetate (38 g) as an off-whitesolid, MP 102-103°C. A mixture of p-butyramidophenyl acetate (38 g),aluminum chloride (80 g) and 1,1,2,2-tetrachloroethane (250 ml) was heatedat 140°C for 3 hours. The reaction mixture was cooled and treated with icedwater. The tetrachloroethane layer was separated and the aqueous layer wasextracted with chloroform. The combined organic layers were extracted with 2N aqueous sodium hydroxide and the alkaline solution was acidified to pH 5with concentrated hydrochloric acid. The acidified solution was extracted withchloroform and the chloroform extract was dried and concentrated underreduced pressure to give 5'-butyramido-2'-hydroxyacetophenone (15.6 g), MP114-117°C. A solution of 5'-butyramido-2'-hydroxyacetophenone (15.6 g) in ethanol (100 ml) was added to an ethanolic solution of sodium ethoxide whichwas prepared from sodium (1.62 g) and ethanol (100 ml). The resultingsolution was evaporated to dryness under reduced pressure anddimethylformamide (100 ml) was added to the solid residue. Approximately10 ml of dimethylformamide was removed by distillation under reducedpressure. Epichlorohydrin (25 ml) was added and the solution was heated at100°C for 4 hours. The solution was concentrated under reduced pressure togive a residual oil which was treated with water to give a solid. The solid wasdissolved in ethanol and the resulting solution was treated with charcoal,filtered and concentrated under reduced pressure to give crude 5'-butyramido-2'-(2,3-epoxypropoxy)acetophenone (16 g), MP 110-116°C.
The crude compound may be purified by recrystallization from ethyl acetate,after treatment with decolorizing charcoal, to give pure 5'-butyramido-2'-(2,3-epoxypropoxy)acetophenone, MP 136-138°C. |
| Brand name | Sectral(Dr. Reddy’s). |
| Therapeutic Function | beta-Adrenergic blocker |
| Safety Profile | Poison by ingestion, subcutaneous,intravenous, and intraperitoneal routes. An experimentalteratogen. Other experimental reproductive effects. Whenheated to decomposition it emits toxic fumes of NOx andHCl. |
Acebutolol hydrochloride Preparation Products And Raw materials
| Raw materials | Isopropylamine-->Acetyl chloride-->Sodium ethoxide-->Aluminum chloride-->Epichlorohydrin |
