70970-06-8

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 99-08-1 1-methyl-3-nitrobenzene 
• 127-09-3 sodium acetate 

Downstream Products

• 99-61-6 3-nitro-benzaldehyde 

Relevant academic research and scientific papers

Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic sp 3 C-H Bonds with Potassium Bromide/Oxone at Room Temperature

Benzylic sp 3 C-H bonds have been successfully brominated with potassium bromide by using Oxone as an oxidant in water/dichloromethane under visible light at room temperature. Toluene, ethylbenzene and other alkylbenzenes bearing an electron-withdrawing group, such as Br, Cl, COMe, CO 2 Et, CO 2 H, CN or NO 2, provide the corresponding benzylic monobromides in good to excellent yields in this reaction. Dibromides can also be produced in the presence of excess potassium bromide in a prolonged reaction time. Control of the illuminance of visible light (~500 lux) is crucial to achieving both high yield and high selectivity in these brominations. Mono- and difluorides can be conveniently prepared through nucleophilic substitutions of the benzylic bromides with potassium fluoride.

Halogenation through Deoxygenation of Alcohols and Aldehydes

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

Thiol-activated gem-dithiols: A new class of controllable hydrogen sulfide donors

A class of novel thiol-activated H2S donors has been developed on the basis of the gem-dithiol template. These donors release H2S in the presence of cysteine or GSH in aqueous solutions as well as in cellular environments.

High selectively oxidative bromination of toluene derivatives by the H 2O2-HBr system

An aqueous solution of hydrogen peroxide and hydrogen bromide illuminated by a 60 W incandescent light bulb serves as a source of bromine radicals. Various substituted toluenes (NO2, Cl, Br, H, CH3) were high selectively brominated at the benzyl position for monobromination in CH2Cl2 at ice water with catalyst free. This simple but effective bromination of toluene derivatives with an aqueous H2O 2-HBr system is characterized with the use of inexpensive reagents and a lower impact on the environment, which make it a good alternative to the existing bromination methods.

Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions

The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.

Synthesis of bromoalkenes and alkylidene dibromides by reactions of carbonyl compounds with 2,4,4,6-tetrabromo-2,5-cyclohexadienone in the presence of triphenylphosphine

Reactions of aliphatic and aromatic aldehydes with the 2,4,4,6-tetrabromo-2,5-cyclohexadienone-triphenylphosphine complex result in formation of the corresponding geminal dibromides. Ketones react with the same complex to give vinyl bromides.

Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes with N-Bromosuccinimide

Tri- and dibromination of methyl-, dimethyl-, and trimethylbenzenes with N-bromosuccinimide were accomplished by photothermal reaction with a tungsten lamp in carbon tetrachloride or benzene. (Dibromomethyl)arenes and (tribromomethyl) derivatives were produced depending upon a solvent used and a substituent on the benzene ring.In the bromination of methylbenzenes without a substituent on the ortho-position, (tribromomethyl)benzenes were formed.On the other hand, ortho-substituted methylbenzenes gave (dibromomethyl)benzenes. α,β-Dibromo-1,2-diarylstilbenes were formed via the debrominative carbon-carbon coupling reaction of ...

Benzylic Bromination-Acetoxylation of Toluenes by Bromide Ion Catalyzed Thermal Decomposition of Peroxydisulfate in Acetic Acid in the Presence of Acetate Ions

Side-chain bromination and acetoxylation of alkylaromatics by halide ion induced decomposition of potassium peroxydisulfate in acetic acid have been studied by product analysis techniques.Catalytic amounts of lithium bromide in the presence of sodium acetate were found effective in promoting benzylic bromination, followed by conversion to the corresponding benzyl acetates by reaction with acetate.The reaction is interpreted to take place by the redox and free-radical chain mechanism involving bromine atoms (ρ = -1.38 vs. ? + for substituted toluenes).In competiti ve experiments, benzyl and 4-nitrobenzyl acetates were found lees reactive than the corresponding toluenes in acetic acid with the couple S2O82-/Br- but more reactive in carbon tetrachloride with N-bromosuccinimide.