81024-42-2

Basic information

• Product Name: (S)-(-)-METOPROLOL
• Synonyms: (S)-(-)-METOPROLOL;2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-, (2S)- (9CI);2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-, (S)-;(2S)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-2-propanol;Metoprolol S-Isomer;[(2S)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(1-methylethyl)-amino]propan-2-ol
• CAS NO: 81024-42-2
• Molecular Formula: C₁₅H₂₅NO₃
• Molecular Weight: 267.36
• Product Categories: Amine;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;API Reference Standard
• Mol File: 81024-42-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 41-43°C
• Boiling Point: 398.6 °C at 760 mmHg
• Flash Point: 194.9 °C
• Appearance: /
• Density: 1.033 g/cm³
• Vapor Pressure: 4.52E-07mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: (S)-(-)-METOPROLOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-METOPROLOL(81024-42-2)
• EPA Substance Registry System: (S)-(-)-METOPROLOL(81024-42-2)

Safety Data

• Hazardous Substances Data: 81024-42-2(Hazardous Substances Data)

Usage

Chemical Properties

Light Beige Low Melting Solid

Uses

Different sources of media describe the Uses of 81024-42-2 differently. You can refer to the following data:
1. (S)-Enantiomer of Metoprolol. Antihypertensive; antianginal; antiarrhythmic (class II).
2. (S)-Enantiomer of Metoprolol. Antihypertensive; antianginal; antiarrhythmic (class II)

InChI:InChI=1/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3/t14-/m0/s1

Upstream product

• 51384-51-1 (RS)-metoprolol 
• 929205-75-4 (R)-1-iodo-3-[4-(2-methoxy ethyl)phenoxy]propan-2-ol 
• 75-31-0 isopropylamine 
• 56718-70-8 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane 
• 56718-71-9 4-(2-methoxyethyl)phenol 
• 80448-05-1 3-[4-(2-methoxyethyl)phenoxy]propylene 
• 133397-54-3 (R)-2-{[4-(2-methoxyethyl)phenoxy]methyl}oxirane 
• 105780-38-9 (2S)-2-{[4-(2-Methoxyethyl)phenoxy]methyl}oxirane 
• 114218-34-7 (R)-1-O-methanesulfonyl-3-O-p-(2-methoxyethyl)phenylglyserol 
• 104450-90-0 2,2'-O-methylenebis<(R)-1-O-methanesulfonyl-3-O-p-(2-methoxyethyl)phenylglycerol> 
• 114218-32-5 1,6-bis-O-p-(2-methoxyethyl)phenyl-3,4-O-methoxymethylene-2,5-O-methylene-D-mannitol 
• 104450-88-6 2,2'-O-methylenebis<3-O-p-(2-methoxyethyl)phenyl-(R)-glyceraldehyde> 
• 104450-87-5 1,6-bis-O-p-(2-methoxyethyl)phenyl-2,5-O-methylene-D-mannitol 
• 104450-89-7 2,2'-O-methylenebis<(S)-1-O-p-(2-methoxyethyl)phenylglycerol> 

Downstream Products

• 207983-04-8 (S)-metoprolol succinic acid 
• 114218-35-8 (-)-Metoprolol hydrochloride 
• 110458-47-4 (1'S,2S)-3-<4-(1-hydroxy-2-methyloxyethyl)phenoxy>-1-(isopropylamino)-2-propanol 
• 110458-48-5 (1'R,2S)-3-<4-(1-hydroxy-2-methyloxyethyl)phenoxy>-1-(isopropylamino)-2-propanol 

Relevant articles and documents

Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC

A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.

Light-assisted preparation of a cyclodextrin-based chiral stationary phase and its separation performance in liquid chromatography

A cyclodextrin-based chiral stationary phase (CD-CSP) is one of the most widely applied CSPs due to its powerful enantioseparation ability. In this study, a facile method was developed to prepare a CD-CSP via carboxyl methyl β-cyclodextrin (CD-COOH) and diazo-resin (DR). Monodisperse silica particles were synthesized using a modified St?ber method. Then DR and CD-COOH were coated on the silica particles via ionic bonding successively and UV light was finally used to couple silica, DR and CD-COOH and the ionic bonds turned into covalent bonds. The resultant CD-DR silica particles were characterized using Fourier transform infrared spectroscopy (FT-IR), thermo-gravimetric analysis (TGA) and scanning electron microscopy (SEM). The enantioselectivity of the CD@SiO2 particles was explored in reversed phase high-performance liquid chromatography (RP-HPLC). Baseline separation of chiral drugs was achieved and the effects of separation parameters (elution mode, buffer and analyte mass) were investigated in detail. By using water soluble non-toxic DR to replace a highly toxic and moisture sensitive silane agent to modify silica microspheres, this light-assisted strategy can provide a green and effective technique to manufacture packing materials for enantioseparation applications.

Method using tartrate-polybasic acid complex to extract and separate metoprolol enantiomer

The invention relates to a new method for extracting and separating metoprolol enantiomer in a chirality manner. The method has the advantages that the high selectivity of tartrate-polybasic acid complex to R type and S type metoprolol enantiomer is utilized, separation factors reaches above 2.2, the centrifuge acting force of a centrifugal extractor is utilized to strengthen mass transfer efficiency, mass transfer and reaction of the metoprolol enantiomer in water phase and organic phase are accelerated, and extraction phase and raffinate phase outlet purity and productivity are increased greatly; the problem that the common extraction technology is low in mass transfer efficiency, single-stage extraction purity and yield is solved; fast and high-selectivity separation of metoprolol can be achieved by multistage counter-flow extraction, and the method is simple in equipment and simple to operate.