(R)-pindolol

Base Information

• Chemical Name: (R)-pindolol
• CAS No.: 68374-35-6
• Molecular Formula: C14H20 N2 O2
• Molecular Weight: 248.325
• DSSTox Substance ID: DTXSID40218506
• Nikkaji Number: J221.535G
• Wikidata: Q27121120
• Pharos Ligand ID: RM3D979CPGH7
• Metabolomics Workbench ID: 56923
• ChEMBL ID: CHEMBL1530633
• Mol file: 68374-35-6.mol

Synonyms:(R)-pindolol;(R)-(+)-pindolol;(+)-pindolol;CHEBI:48280;68374-35-6;(2R)-1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol;(2R)-1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol;(2R)-1-(1H-indol-4-yloxy)-3-((1-methylethyl)amino)-2-propanol;2-Propanol, 1-(1H-indol-4-yloxy)-3-((1-methylethyl)amino)-, (R)-;CAS-13523-86-9;Tocris-0994;Lopac-P-152;Lopac-P-152-Batch2;Lopac-P-0778;SCHEMBL1157556;CHEMBL1530633;DTXSID40218506;PDSP1_001585;PDSP2_001569;NCGC00015786-01;NCGC00015786-02;NCGC00015786-03;NCGC00015786-04;NCGC00015786-05;NCGC00015786-12;NCGC00016700-01;NCGC00024925-01;Q27121120;(R)-1-(1H-Indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol

Chemical Property of (R)-pindolol

Chemical Property:

• Vapor Pressure: 3.77E-09mmHg at 25°C
• Boiling Point: 457.1°C at 760 mmHg
• PKA: 13.94±0.20(Predicted)
• Flash Point: 230.3°C
• PSA: 57.28000
• Density: 1.152g/cm³
• LogP: 2.29650
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 248.152477885
• Heavy Atom Count: 18
• Complexity: 248

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=C1C=CN2)O
• Isomeric SMILES: CC(C)NC[C@H](COC1=CC=CC2=C1C=CN2)O

Technology Process of (R)-pindolol

There total 2 articles about (R)-pindolol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

acetone (67-64-1) + (S)-4-(2-hydroxy-3-nitropropoxy)indole (160319-71-1) → (+)-Pindolol (68374-35-6) + (S)-pindolol (26328-11-0)

Guidance literature:

With platinum(IV) oxide; hydrogen; In methanol; at 50 ℃; for 16h;

DOI:10.1016/S0040-4020(01)89540-5

Reference yield:

1-(1H-indol-4-yloxy)-3-(isopropylamino)-2-propanol (13523-86-9) → (+)-Pindolol (68374-35-6) + (S)-pindolol (26328-11-0)

Guidance literature:

resolving agent: trans-cellulose tris(4-phenylazophenylcarbamate) ( CPAPC ) adsorbed on silica gel; optical resolution degree examined by HPLC on cis/trans-CPAPC;

DOI:10.1246/cl.1986.983

Reference yield: 92.0%

chloro-diphenylphosphine (1079-66-9,74391-44-9) + (+)-Pindolol (68374-35-6) → (R)-PINDOPHOS

Guidance literature:

With triethylamine; In benzene; for 4h; Heating;

DOI:10.1016/0957-4166(96)00105-X

upstream raw materials:

1-(1H-indol-4-yloxy)-3-(isopropylamino)-2-propanol

acetone

(S)-4-(2-hydroxy-3-nitropropoxy)indole

Refernces

• 1、 Liu, Yi,Sombra, Lorena L.,Stege, Patricia W.. "Enantiomeric separation of β-blockers and tryptophan using heparin as stationary and pseudostationary phases in capillary electrophoresis". . p. 988 - 995. Retrieved 2018/07/29.
• 2、 Gong, Yinhan,Lee, Hian Kee. "Application of cyclam-capped β-cyclodextrin-bonded silica particles as a chiral stationary phase in capillary electrochromatography for enantiomeric separations". . p. 1348 - 1354. Retrieved 2007/10/03.