55329-66-3

Upstream product

• 108-24-7 acetic anhydride 
• 620-22-4 3-Methylbenzonitrile 
• 108-38-3 m-xylene 
• 75-05-8 acetonitrile 
• 1309380-85-5 C₂₀H₁₉NO₃S 
• 1074-82-4 potassium phtalimide 
• 620-19-9 1-chloromethyl-3-methyl-benzene 
• 7116-51-0 α-methoxy-m-xylene 
• 100-81-2 3-methyl-benzenemethanamine 
• 75-36-5 acetyl chloride 

Downstream Products

• 620-23-5 m-tolyl aldehyde 
• 99-04-7 m-Toluic acid 

Relevant academic research and scientific papers

Acetonitrile and benzonitrile as versatile amino sources in copper-catalyzed mild electrochemical C-H amidation reactions

A mild, efficient electrochemical approach to the site-selective direct C-H amidation of benzene and its derivatives with acetonitrile and benzonitrile has been developed. It has been shown that joint electrochemical oxidation of various arenes in the presence of a copper salt as a catalyst and nitriles leads to the formation of N-phenylacetamide from benzene and N-benzylacetamides from benzyl derivatives (up to 78% yield). A favorable feature of the process is mild conditions (room temperature, ambient pressure, no strong oxidants) that meet the criteria of green chemistry.

Dynamic path bifurcation in the Beckmann reaction: Support from kinetic analyses

The reactions of oximes to amides, known as the Beckmann rearrangement, may undergo fragmentation to form carbocations + nitriles when the migrating groups have reasonable stability as cations. The reactions of oxime sulfonates of 1-substituted-phenyl-2-propanone derivatives (7-X) and related substrates (8-X, 9a-X) in aqueous CH3CN gave both rearrangement products (amides) and fragmentation products (alcohols), the ratio of which depends on the system; the reactions of 7-X gave amides predominantly, whereas 9a-X yielded alcohols as the major product. The logk-logk plots between the systems gave excellent linear correlations with slopes of near unity. The results support the occurrence of path bifurcation after the rate-determining TS of the Beckmann rearrangement/fragmentation reaction, which has previously been proposed on the basis of molecular dynamics simulations. It was concluded that path-bifurcation phenomenon could be more common than thought and that a reactivity-selectivity argument based on the traditional TS theory may not always be applicable even to a well-known textbook organic reaction.

Benzyl amide-ketoacid inhibitors of HIV-integrase

Integrase is one of three enzymes expressed by HIV and represents a validated target for therapy. Previous reports have demonstrated that the diketoacid-based chemotype is a useful starting point for the design of inhibitors of this enzyme. In this study, one of the ketone groups is replaced by a benzylamide resulting in a new potent chemotype. A preliminary SAR study is carried out to investigate the substitution requirements on the phenyl ring and methylene group of the benzylamide.

Simple, high yield preparation of N-benzylacetamides by Lewis acid-catalysed reaction of benzyl chlorides or benzyl methyl ethers with acetonitrile

Reaction of either benzyl chlorides or benzyl methyl ethers with hydrated ferric chloride in acetonitrile results in smooth Ritter reaction and formation of N-benzylacetamides in excellent yield.