3102-00-9

Basic information

• Product Name: Febuprol
• Synonyms: (3-n-butoxy-2-hydroxypropyl)phenylether;1-butoxy-3-phenoxy-2-propano;1-butoxy-3-phenoxy-2-propanol;3-n-butoxy-1-phenoxy-2-propanol;h-33;k-10033;1-butoxy-3-(phenoxy)propan-2-ol;FEBUPROL
• CAS NO: 3102-00-9
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.3
• EINECS: 221-454-8
• Product Categories: API
• Mol File: 3102-00-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 25°C
• Boiling Point: bp11 165°; bp1.0 125-132°
• Flash Point: 163.1 °C
• Appearance: /
• Density: d420 1.027
• Vapor Pressure: 2.25E-05mmHg at 25°C
• Refractive Index: nD20 1.5004
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Febuprol(CAS DataBase Reference)
• NIST Chemistry Reference: Febuprol(3102-00-9)
• EPA Substance Registry System: Febuprol(3102-00-9)

Safety Data

• Hazardous Substances Data: 3102-00-9(Hazardous Substances Data)

Usage

Originator

Valbil,Rohm Pharma,W. Germany,1981

Manufacturing Process

Initially, 4.5 g (0.08 mol) pulverized potassium hydroxide was dissolved in 300 ml isopropanol in a 500 ml four-neck flask equipped with stirrer, intensive cooler, dropping funnel and feed pipe for the gas treatment with nitrogen.Then, 52.0 g (0.4 mol) n-butylglycidyl ether and 41.4 g (0.44 mol) phenol was added thereto, whereafter the material was heated to boiling under nitrogen. The material was stirred, about 8.5 hours, until no glycidyl ether could be determined, e.g., by gas chromatography.After the suspension was cooled under nitrogen, the solvent was distilled off under vacuum. The residue was taken up in 200 ml water and the milky emulsion extracted exhaustively with ether. From the organic phase, the excess butylglycidyl ether was extracted with diluted potassium hydroxide solution. The ether phase was washed neutral with water and the solvent removed after drying with sodium sulfate. The remaining oily residue was distilled under vacuum; there was obtained a colorless liquid of BP 123.5°C/0.07 mm. Yield: 81.8 g (91.1% of the theory)

Therapeutic Function

Choleretic

InChI:InChI=1/C13H20O3/c1-2-3-9-15-10-12(14)11-16-13-7-5-4-6-8-13/h4-8,12,14H,2-3,9-11H2,1H3

Upstream product

• 122-60-1 Phenyl glycidyl ether 
• 71-36-3 butan-1-ol 
• 5593-70-4 titanium (IV) butoxide 

Relevant articles and documents

Asymmetric Transfer Hydrogenation of 1,3-Alkoxy/Aryloxy Propanones Using Tethered Arene/Ru(II)/TsDPEN Complexes

A series of propanones containing combinations of aryloxy and alkoxy substituents at the 1- and 3-positions were reduced to the alcohols via asymmetric transfer hydrogenation using a tethered Ru(II)/TsDPEN catalyst. The enantioselectivities of the reductions reveal a complex pattern of electronic and steric effects which, when used in a matched combination, can lead to the formation of products of up to 68% ee (84:16 er) from this highly challenging class of substrate.

Reaction of 2,3-epoxypropyl ethers with 1-butanol

Nucleophilic opening of the oxirane ring in 2,3-epoxypropyl ethers with alcohols in the presence of titanium alkoxides and other catalysts was studied. The mechanism of catalysis by titanium alkoxides was discussed on the basis of comparison with acid-bas

ALKOXYLATION OF SUBSTITUTED OXIRANES BY ALKOXYTITANIUN TOSYLATES

Under mild conditions alkoxytitanium tosylates convert substituted oxiranes into the monoethers of 1,2-glycols with high regioselectivity.