40747-12-4

Basic information

• Product Name: (E)-1-(1H-indol-3-yl)ethanone oxime
• CAS NO: 40747-12-4
• Molecular Weight: 174.202
• Mol File: 40747-12-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (E)-1-(1H-indol-3-yl)ethanone oxime(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(1H-indol-3-yl)ethanone oxime(40747-12-4)
• EPA Substance Registry System: (E)-1-(1H-indol-3-yl)ethanone oxime(40747-12-4)

Safety Data

• Hazardous Substances Data: 40747-12-4(Hazardous Substances Data)

Upstream product

• 703-80-0 3-acetylindole 
• 120-72-9 indole 

Downstream Products

• 51030-59-2 N-(1H-indol-3-yl)acetamide 

Relevant articles and documents

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate

A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.

An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)

An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.