152520-56-4

Basic information

• Product Name: Nebivolol hydrochloride
• Synonyms: Narbivolol;rel-(aR,a′R,2R,2′S)-a,a′-[iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] hydrochloride;Nebivolol hydrochloride, >=98%;RAC NEBIVOLOL, HYDROCHLORIDE;a,a(Iminodimethylene)bis[6-fluoro-2-chromanmethanol] Hydrochloride;Lobivon;Nebilet;Nebilox
• CAS NO: 152520-56-4
• Molecular Formula: C22H26ClF2NO4
• Molecular Weight: 441.8959464
• EINECS: 1806241-263-5
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;R-67145
• Mol File: 152520-56-4.mol
• Article Data: 29

Chemical Properties

• Melting Point: 220-222°C
• Boiling Point: 600.5 °C at 760 mmHg
• Flash Point: 316.9 °C
• Appearance: white to off-white/
• Vapor Pressure: 2.88E-15mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: ≥20mg/mL
• Merck: 14,6432
• CAS DataBase Reference: Nebivolol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Nebivolol hydrochloride(152520-56-4)
• EPA Substance Registry System: Nebivolol hydrochloride(152520-56-4)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: 3077
• WGK Germany: 3
• Hazardous Substances Data: 152520-56-4(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Powder

Uses

Different sources of media describe the Uses of 152520-56-4 differently. You can refer to the following data:
1. Nebivolol selectively inhibits β1-adrenoceptor with IC50 of 0.8 nM
2. Nebivolol Hydrochloride is a highly selective β1-adrenoceptor antagonist.

Biological Activity

Highly selective β 1 -adrenoceptor antagonist (K i values are 0.88, 20, 44, 700, 1160, 2400 and 4000 nM at β 1 , 5-HT 1A , β 2 , 5-HT 2 , α 1 , H 1 and D 2 receptors respectively). Induces vasodilation via a nitric oxide- and cGMP-dependent mechanism (EC 50 = 11.36 μ M in renal arteries) and displays antihypertensive activity in vivo .

Biochem/physiol Actions

Nebivolol hydrochloride (NEB) is used as a racemic mixture for clinical studies. It stabilizes membrane and possesses intrinsic sympathomimetic functionality. Nebivolol interaction with π-acceptors (2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,4-dinitrophenol (DNP) and 2,4,6-trinitrophenol (picric acid; PA)) is useful in the spectrophotometric detection methods.

InChI:InChI=1/C22H25F2NO4.ClH/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22;/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2;1H

Upstream product

• 129050-26-6 (2R)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene 
• 303176-43-4 1-[6-fluoro-(2R)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol 
• 1199945-26-0 2-{benzyl-[2-(6-fluoro-chroman-2-yl)-2-hydroxy-ethyl]-amino}-1-(6-fluoro-chroman-2-yl)-ethanol 
• 1345202-57-4 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl-2,2-dimethylpropanoate 
• 1345202-60-9 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-tosyloxyethyl-2,2-dimethylpropanoate 
• 1345202-52-9 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-hydroxyethyl acetate 
• 1345202-53-0 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl acetate 
• 929706-85-4 N-benzylnebivolol 
• 929706-85-4 (+/-)-[2R*[S*[R*(S*)]]]-α,α'-[[(phenylmethyl)imino]bis(methylene)]bis[6-fluoro-chroman-2-methanol] 
• 496-69-5 2-bromo-4-fluoro-phenol 
• 347-54-6 5-fluoro-2-hydroxybenzaldehyde 
• 303176-40-1 (R)-2-[(S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl-4-methylbenzenesulfonate 
• 303176-36-5 ethyl 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-2-pentenoate 
• 303176-37-6 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol 

Relevant articles and documents

Synthesis of intermediate compound and [...] (by machine translation)

Synthesis of intermediate compounds [a] and [...]. [Solution] a [...], asymmetric epoxidation, sulfonyl halide in the presence of base catalyst by sulfonation, alkylation of amines, such as synthesized by a series of cross-coupling reaction. [Effect] [...] important from the viewpoint of pharmacological value, high efficiency, low cost, and which meets the requirements of industrial, optical isomers may be prepared [...] and develop a method, which is very economical in social benefit. [Drawing] no (by machine translation)

NEBIVOLOL SYNTHESIS METHOD AND INTERMEDIATE COMPOUND THEREOF

The present invention relates to nebivolol synthesis method and intermediate compound thereof. Specifically, the present invention relates to a method for synthesizing nebivolol, intermediate compound thereof, and a method for preparing the intermediate compound.

PROCESS FOR PREPARATION OF NEBIVOLOL AND IT'S SALTS

The present invention discloses a new process for preparation of Nebivolol or it's pharmaceutically acceptable salt. More particularly, the invention discloses an improved economical process for the preparation of intermediate, 6-fluoro-3,4- dihydro-2H-1-benzopyran-2-carboxaldehyde of Formula – II, converting the 6- fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde of Formula – II into mixture of [R*(S*)]-6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran and [R*(R*)]-6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran of Formula-V and separation of diastereomers of (R*)-6-Fluoro-3,4-dihydro-2-((S*)-oxiran-2-yl)- 2H-benzopran by forming azeotrope.