67907-58-8

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 100-46-9 benzylamine 
• 70251-03-5 N-benzyl-1-(3-bromophenyl)methanamine 
• 67907-53-3 benzylidene-(3-bromo-benzyl)-amine 
• 141-52-6 sodium ethanolate 

Downstream Products

• 67907-53-3 benzylidene-(3-bromo-benzyl)-amine 
• 1072488-32-4 C₁₆H₁₆BrN 

Relevant academic research and scientific papers

Deep eutectic solvent catalyzed eco-friendly synthesis of imines and hydrobenzamides

The urea-choline chloride-based deep eutectic solvent was found to be an efficient catalyst and reaction media for the additive-free synthesis of imines (Schiff bases) and hydrobenzamides by the reaction of aldehydes with amines and ammonia in good to high yields. Outstanding features of this protocol were the general and atom-economical reaction, absence of external catalysts and additives, simple workup, and availability and recycling of urea-choline chloride as a green solvent. Graphical abstract: (Chemical Equation Presented).

Concise synthesis of spergualin-inspired molecules with broad-spectrum antibiotic activity

There is a growing need to identify new, broad-spectrum antibiotics. The natural product spergualin was previously shown to have promising anti-bacterial activity and a privileged structure, but its challenging synthesis had limited further exploration. For example, syntheses of spergualin and its analogs have been reported in approximately 10 linear steps, with overall yields between 0.3 and 18%. Using the Ugi multi-component reaction, we assembled spergualin-inspired molecules in a single step, dramatically improving the overall yield (20% to 96%). Using this strategy, we generated 43 new analogs and tested them for anti-bacterial activity against two Gram-negative and four Gram-positive strains. We found that the most potent analogue, compound 6, had MIC values between 4 and 32 μg mL-1 against the six strains, which is a significant improvement on spergualin (MIC ~ 6.25 to 50 μg mL-1). These studies provide a concise route to a broad-spectrum antibiotic with a novel chemical scaffold. This journal is

IBX works efficiently under solvent free conditions in ball milling

IBX (2-iodoxybenzoic acid), discovered in 1893, is an oxidant in synthetic chemistry whose extensive use is impeded by its explosiveness at high temperature and poor solubility in common organic solvents except DMSO. Since the discovery of Dess-Martin Periodinane in 1983, several modified IBX systems have been reported. However, under ball milling conditions, IBX works efficiently with various organic functionalities at ambient temperature under solvent free conditions. Also, the waste IBA (2-iodosobenzoic acid) produced from the reactions was in situ oxidized to IBX in the following step using oxone and thus reused for multiple cycles by conserving its efficiency (only ～6% loss after 15 cycles). This work describes an overview of a highly economical synthetic methodology which overcomes the problems of using IBX, efficiently in gram scale and in a non-explosive way. This journal is the Partner Organisations 2014.

Synthesis of a natural product-inspired eight-membered ring lactam library via ring-closing metathesis

We have prepared a novel speculative eight-membered lactam demonstration library based on the skeletal structure of the potent antitumor marine natural product octalactin A. The basic scaffold was readily constructed in a convergent fashion via ring-closing metathesis chemistry from the corresponding diene amides. A cursory examination of the biological properties of the library validates the relevance and significance of these structures.