28363-24-8

Usage

Type of compound

Nitrile

Contains

Bromine atom, aniline group (benzene ring with attached amino group)

Usage

Building block in organic synthesis and pharmaceutical research, production of various pharmaceutical compounds and active ingredients, creation of new materials, synthesis of dyes and other organic compounds.

Upstream product

• 50-00-0 formaldehyd 
• 106-40-1 4-bromo-aniline 
• 372-09-8 cyanoacetic acid 
• 590-17-0 cyanomethyl bromide 
• 7677-24-9 trimethylsilyl cyanide 
• 2617-78-9 N-(4-bromophenyl)formamide 

Downstream Products

• 213995-52-9 2-(4-bromophenylamino)acetamide 
• 157671-45-9 2-[(4-bromophenyl)(methyl)amino]acetonitrile 

Relevant academic research and scientific papers

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids

Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of α-aminonitriles and cyanomethyl esters with good yields and excellent functionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. Iodoacetonitrile was generated in situ from the iodination-decarboxylation of cyanoacetic acid in this transformation.

PYRROLE AND PYRAZOLE DERIVATIVES AS POTENTIATORS OF GLUTAMATE RECEPTORS

The present invention relates to pyrrole and pyrazole compounds of formula (I) and their pharmaceutically acceptable salts, and further relates to their use in treating schizophrenia, cognitive deficits associated with schizophrenia, Alzheimer's disease, dementia of the Alzheimer's type, mild cognitive impairment, or depression. The compounds act as potentiators on glutamate receptors, in particular AMPA and the GluR family.