1233200-21-9

Basic information

• Product Name: (Z)-acetophenone O-benzyloxime
• Synonyms: (Z)-acetophenone O-benzyloxime
• CAS NO: 1233200-21-9
• Molecular Weight: 225.29
• Mol File: 1233200-21-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (Z)-acetophenone O-benzyloxime(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-acetophenone O-benzyloxime(1233200-21-9)
• EPA Substance Registry System: (Z)-acetophenone O-benzyloxime(1233200-21-9)

Safety Data

• Hazardous Substances Data: 1233200-21-9(Hazardous Substances Data)

Usage

General Description

(Z)-acetophenone O-benzyloxime is a chemical compound with a molecular formula of C14H13NO. It is a yellow powder that is soluble in organic solvents and has a melting point of approximately 79-81°C. (Z)-acetophenone O-benzyloxime is commonly used as a reagent in organic synthesis and is involved in a variety of reactions, including the Beckmann rearrangement and the Hofmann rearrangement. It is a useful intermediate for the preparation of various compounds and is also used in the production of pharmaceuticals and agrochemicals. Additionally, it has potential applications in the fields of medicine and materials science.

Upstream product

• 28570-76-5 (E)-ethanone-1-phenyl-O-(phenylmethyl)oxime 
• 17082-13-2 α-bromoacetophenone oxime 
• 70-11-1 α-bromoacetophenone 
• 50314-86-8 acetophenone oxime 
• 100-39-0 benzyl bromide 
• 98-86-2 acetophenone 
• 613-91-2 acetophenone oxime 
• 100-51-6 benzyl alcohol 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 

Downstream Products

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 36283-44-0 N-acetyl-1-phenylethylamine 

Relevant articles and documents

Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products

Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.

An efficient one-pot synthesis of oxime ethers from alcohols using triphenylphosphine/carbon tetrachloride

A convenient and efficient one-pot O-alkylation of oximes from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, oxime, and DBU in the presence of catalytic amounts of tetrabutylammonium iodide in refluxing acetonitrile regioselectively furnishes the corresponding O-alkyl ethers in good yields. This methodology is highly efficient O-alkylation of oximes with various structurally diverse alcohols. Semiempirical quantum-mechanic calculations (AM1) for unsymmetrical oxime ethers, indicated a lower heat of formation for Z-isomers. Georg Thieme Verlag Stuttgart - New York.