127792-49-8

Usage

Uses

Used in Academic Research:
2-Bromo-5-chlorophenylacetonitrile is used as a chemical intermediate for the synthesis of more complex organic molecules, primarily in academic research settings. Its reactivity and unique structure make it a valuable compound for exploring new chemical reactions and pathways.
Used in Organic Synthesis:
2-Bromo-5-chlorophenylacetonitrile is used as a building block in the preparation of various organic compounds. Its bromo and chloro substituents allow for further functionalization and modification, making it a versatile starting material for the development of new molecules with potential applications in various fields.
Although 2-Bromo-5-chlorophenylacetonitrile has not found significant applications in the pharmaceutical or chemical industry, its production is generally confined to laboratory sizing for academic research purposes. This is due to its powerful reactivity and the need for proper handling to ensure safety during its use in chemical reactions.

Upstream product

• 143-33-9 sodium cyanide 
• 112399-50-5 2-bromo-5-fluorobenzyl bromide 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 174265-12-4 2-bromo-5-chlorobenzaldehyde 
• 773837-37-9 sodium cyanide 
• 60666-70-8 2-bromo-5-chlorobenzyl alcohol 
• 14495-51-3 2-bromo-5-chlorotoluene 
• 66192-24-3 2-bromo-5-chlorobenzyl bromide 
• 333-20-0 potassium thioacyanate 
• 151-50-8 potassium cyanide 

Downstream Products

• 127792-43-2 sodium {2-[(2,6-dichlorophenyl)amino]-5-fluorophenyl}acetate 
• 127792-42-1 sodium {2-[(2,6-dichloro-4-fluorophenyl)amino]-5-fluorophenyl}acetate 
• 1017581-68-8 [2-(3,4-dimethoxyphenylethynyl)-5-fluorophenyl]acetonitrile 
• 866029-28-9 2-(2-bromo-5-fluorophenyl)ethan-1-ol 
• 739336-26-6 2-(2-bromo-5-fluorophenyl) acetic acid 
• 17630-75-0 5-chloro-indolin-2-one 
• 1314790-02-7 2-(2-bromo-5-chlorophenyl)-2-methylpropanenitrile 
• 1379974-95-4 2-(2-bromo-5-chlorophenyl)ethan-1-amine 
• 1273546-86-3 N-Boc-N-[2-(2-bromo-5-chloro-phenyl)ethyl]amine 

Relevant academic research and scientific papers

Highly diastereoselective synthesis of tetralin-fused spirooxindoles via lewis acid-catalyzed C(sp3)H bond functionalization

A highly diastereoselective synthesis of tetralin-fused spirooxindole derivatives was described. Treatment of benzylidene oxindoles with a catalytic amount of Sc(OTf)3 in refluxing hexane afforded the target compounds in good chemical yields with excellent diastereoselectivities (up to >20:1). Detailed investigation of the reaction mechanism revealed that both interconversion of the two diastereomers and their solubility difference in reaction medium were the key to achieving excellent diastereoselectivities.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

AUTOTAXIN INHIBITORS COMPRISING A HETEROAROMATIC RING-BENZYL-AMIDE-CYCLE CORE

The present invention relates to novel compounds that are autotaxin inhibitors, processes for their preparation, pharmaceutical compositions and medicaments containing them and to their use in diseases and disorders mediated by autotaxin.

Gold-catalyzed 1,2-oxoarylations of nitriles with pyridine-derived oxides

We report the first success in the gold-catalyzed oxoarylations of nitriles with pyridine-derived N-oxides using gold carbenes as initiators. These oxoarylations were also achieved satisfactorily in intermolecular three-component oxidations, including diverse alkenyldiazo esters, nitriles, and pyridine-based oxides. Spill the (car)benes: Reported herein is the first successful gold-catalyzed oxoarylation of nitriles with pyridine-derived N-oxides using gold carbenes as initiators (see scheme; DCE=1,2-dichloroethane, IPr=1,3-bis(diisopropylphenyl)imidazol-2-ylidene). These oxoarylations were also achieved satisfactorily in intermolecular three-component oxidations using a variety of alkenyldiazo esters, nitriles, and pyridine-based N-oxides.

Copper-catalyzed domino coupling reaction: An efficient method to synthesize oxindoles

An efficient and novel procedure for a copper catalyzed domino coupling reaction has been developed, which afforded various oxindoles in good to excellent yields with tolerance of various substituents. In addition, this method could be applied to synthesize horsfiline and coerulescine in few steps with high total yields. The Royal Society of Chemistry 2012.

Phenethyl nicotinamides, a novel class of NaV1.7 channel blockers: Structure and activity relationship

The NaV1.7 ion channel is an attractive target for development of potential analgesic drugs based on strong genetic links between mutations in the gene coding for the channel protein and inheritable pain conditions. The (S)-N-chroman-3-ylcarboxamide series, exemplified by 1, was used as a starting point for development of new channel blockers, resulting in the phenethyl nicotinamide series. The structure and activity relationship for this series was established and the metabolic issues of early analogues were addressed by appropriate substitutions. Compound 33 displayed acceptable overall in vitro properties and in vivo rat PK profile.

Synthesis of benzylisoquinoline derivatives possessing electron-withdrawing substituents on the benzene ring of the isoquinoline skeleton

3,4-Dihydrobenzylisoquinolines and 1,2,3,4-tetrahydrobenzyl-isoquinolines possessing electron withdrawing substituents on the benzene ring of the isoquinoline framework are easily accessible by a synthetic approach that takes advantage of a Sonogashira coupling to build up the C1-C8a bond of the isoquinoline skeleton and a Ti-catalyzed intramolecular hydroamination of an alkyne to close the heterocyclic ring.

Synthesis and quantitative structure-activity relationships of diclofenac analogues

The synthesis of a series of 2-anilinophenylacetic acid, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.