72332-33-3

Basic information

• Product Name: (R*,S*)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone
• Synonyms: (r*,s*)-(-)-8-hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1h)-quinolinone;PROCATEROL;2(1h)-quinolinone,8-hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-,(r*,;8-hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1h)-quinolinone(r*,s;s*)-(+-)-;ent-Florfenicol AMine-d3;(S)-N,N-DiMethyl-3-(1-naphthalenyl-d7-oxy)-3-(2-thienyl)propanaMine;ANTI-SARS VIRUS SM antibody produced in rabbit
• CAS NO: 72332-33-3
• Molecular Formula: C16H22N2O3
• Molecular Weight: 290.36
• EINECS: 276-590-0
• Mol File: 72332-33-3.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 539.5 °C at 760 mmHg
• Flash Point: 280.1 °C
• Appearance: /
• Density: 1.191 g/cm³
• Storage Temp.: -20°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Methanol
• CAS DataBase Reference: (R*,S*)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: (R*,S*)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone(72332-33-3)
• EPA Substance Registry System: (R*,S*)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone(72332-33-3)

Safety Data

• Hazardous Substances Data: 72332-33-3(Hazardous Substances Data)

Usage

Description

(R,S)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone is a complex organic compound with a quinolinone core structure. It features a hydroxy group at the 8th position and a 1-hydroxy-2-((1-methylethyl)amino)butyl group at the 5th position. (R,S)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone is characterized by its off-white solid appearance and exhibits broncholytic properties similar to albuteral, with a more prolonged action.

Uses

Used in Pharmaceutical Industry:
(R,S)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone is used as an intermediate for the synthesis of Florfenicol (F405750), an antibacterial agent. It plays a crucial role in the development of new drugs to combat bacterial infections.
Used in Respiratory Treatment:
(R,S)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone is used as an inhaled drug for treating bronchial asthma. Its broncholytic properties, similar to those of albuteral, make it a valuable compound for managing respiratory conditions by helping to relax and open the airways, providing relief from asthma symptoms.
Chemical Properties:
(R,S)-(-)-8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone is an off-white solid, which is a common physical state for many organic compounds. Its chemical structure and properties contribute to its potential applications in the pharmaceutical industry and respiratory treatment.

Synthesis

Procaterol, 5-[1-hydroxy-2-[(1-methylethyl)amino]butyl]-8-hydroxy-2-(1H) quinolone (23.3.25), is synthesized by acylation of 8-hydroxy-2(1H)-quinolone with 2-bromobutyric acid chloride at the fifth position of the quinoline system, which gives the compound 23.3.23. This undergoes action of isopropylamine, forming an aminoketone 23.3.24, the carbonyl group of which is reduced by sodium borohydride, giving procaterol (23.3.25) .

InChI:InChI=1/C16H22N2O3/c1-4-12(17-9(2)3)16(21)11-5-7-13(19)15-10(11)6-8-14(20)18-15/h5-9,12,16-17,19,21H,4H2,1-3H3,(H,18,20)