118564-89-9

Basic information

• Product Name: 2-(1-HYDROXYLAMINOETHYL)-BENZOTHIOPHENE
• Synonyms: 2-(1-HYDROXYLAMINOETHYL)-BENZOTHIOPHENE;AKOS 91248;N-(1-BENZO[B]THIOPHEN-2-YL-ETHYL)-HYDROXYLAMINE
• CAS NO: 118564-89-9
• Molecular Formula: C₁₀H₁₁NOS
• Molecular Weight: 193.27
• Mol File: 118564-89-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 366.8±44.0 °C(Predicted)
• Appearance: /
• Density: 1.263±0.06 g/cm3(Predicted)
• PKA: 13.08±0.50(Predicted)
• CAS DataBase Reference: 2-(1-HYDROXYLAMINOETHYL)-BENZOTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-HYDROXYLAMINOETHYL)-BENZOTHIOPHENE(118564-89-9)
• EPA Substance Registry System: 2-(1-HYDROXYLAMINOETHYL)-BENZOTHIOPHENE(118564-89-9)

Safety Data

• Hazardous Substances Data: 118564-89-9(Hazardous Substances Data)

Usage

Uses

N-?(1-?Benzo[b]?thiophen-?2-?yl-?ethyl)?-?hydroxylamine is a reagent used in the preparation of Zileuton, an anti-asthmatic drug.

Upstream product

• 136386-26-0 C₇H₁₃NO₂ 
• 95-15-8 Benzo[b]thiophene 
• 147396-07-4 2-acetylbenzothiophene oxime 
• 118564-88-8 2-[1-(hydroxyimino)ethyl]-benzo[b]thiophene 
• 1206596-72-6 O-(trimethylsilyl)-N-(1-benzo[b]thien-2-yl-ethyl)hydroxylamine 
• 1013036-71-9 1-[N-(tert-butoxycarbonyl)-N-(hydroxy)amino]-1-(benzothien-2-yl)ethane 
• 22720-75-8 2-acetyl benzo[b]thiophene 

Downstream Products

• 142606-21-1 zileuton 

Relevant articles and documents

Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines

We found that cyclometalated cyclopentadienyl iridium(III) complexes are uniquely efficient catalysts in homogeneous hydrogenation of oximes to hydroxylamine products. A stable iridium C,N-chelation is crucial, with alkoxy-substituted aryl ketimine ligand

PROCESS FOR THE PREPARATION OF ZILEUTON

Process for preparing a compound of formula (I), or a salt thereof, comprising reacting of a compound of formula (II) wherein X and R are as herein defined; with a compound of formula (III) [in-line-formulae]NH2OZ??(III)[/in-line-formulae] wherein Z is a hydroxy protecting group, in presence of a catalyst, to obtain a compound of formula (IV), or a salt thereof, removing the hydroxyl protecting group to obtain a compound of formula (V), or a salt thereof; converting a compound of formula (V), or a salt thereof, into a compound of formula (I), or a salt thereof; and, if desired, converting a compound of formula (I) into a salt thereof, or vice versa.

Structure-activity relationships of N-hydroxyurea 5-lipoxygenase inhibitors

The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure- activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N- [3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hydroxyurea (17c) was identified and selected for clinical development.