584-48-5

Usage

Uses

Used in Chemical Synthesis:
1-Bromo-2,4-dinitrobenzene is used as a chemical intermediate for the preparation of 2,4-dinitrophenol via treatment with KO2-crown ether complex in benzene. This synthesis is important for the production of various chemical compounds and materials.
Used in Biochemical Assays:
1-Bromo-2,4-dinitrobenzene serves as a substrate in protein determination and glutathione S-transferase (GST) assays. It is particularly used in the assays of chicken and rat prostaglandin D2 synthase (PGDS), which are important enzymes involved in various biological processes.

Purification Methods

Crystallise it from ethyl ether, isopropyl ether, 80% EtOH or absolute EtOH. [Beilstein 5 III 640, 5 IV 749.]

InChI:InChI=1/C6H3BrN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

Upstream product

• 108-86-1 bromobenzene 
• 97-02-9 2,4-Dinitroanilin 
• 32578-27-1 2,4-dinitrophenyl trifluoromethanesulfonate 
• 401631-88-7 C₈H₉N₅O₄ 
• 106-95-6 allyl bromide 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 76195-86-3 2,4-dinitrophenylhydrazine hydrochloride 
• 610-30-0 2,4-dinitrobenzoic acid 
• 586-78-7 para-nitrophenyl bromide 
• 5467-74-3 4-Bromophenylboronic acid 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 42996-92-9 2,4-dinitronitrosobenzene 

Downstream Products

• 113342-96-4 1-(2,4-dinitro-phenyl)-2,5-dihydro-pyrrole 
• 5920-23-0 1-(2,4-dinitro-phenyl)-3-ethyl-4,5-dihydro-1H-pyrazole 
• 109597-97-9 3,5-diethyl-1-(2,4-dinitro-phenyl)-pyridinium; bromide 
• 13059-84-2 2,4-dinitro-N-propylaniline 
• 51-28-5 2,4-Dinitrophenol 
• 5833-18-1 ethyl 2,2-bis(2,4-dinitrophenyl)acetate 
• 610-54-8 2,4-dinitro-1-ethoxybenzene 
• 52790-65-5 N-(2,4-dinitrophenyl)hexylamine 
• 2217-55-2 bis(2,4-dinitrophenyl) disulphide 
• 857592-35-9 N-(2,4-dinitrophenyl)-methyl-n-propylamine 
• 106276-26-0 (2,4-dinitro-phenyl)-phenethyl ether 
• 5833-19-2 bis-(2,4-dinitro-phenyl)-acetic acid methyl ester 
• 4603-74-1 (4-bromo-phenyl)-(2,4-dinitro-phenyl)-amine 
• 18016-88-1 [2-(2,4-dinitro-anilino)-phenyl]-arsonic acid 

Relevant academic research and scientific papers

Metal- and base-free synthesis of aryl bromides from arylhydrazines

An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.

PROCESS FOR THE PREPARATION OF ORGANIC HALIDES

The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.

Novel carbazole sulfonamide derivatives of antitumor agent: Synthesis, antiproliferative activity and aqueous solubility

The current optimization of IG-105 (3) on the carbazole-ring provided a series of new carbazole sulfonamides derivatives 13a–13m. All of the compounds have been evaluated against HepG2 cells (hepatoma cancer) for antiproliferative activity. Compounds that showed activity better or comparable to that of 3 versus HepG2 were evaluated against MCF-7 (breast cancer), MIA PaCa-2 (pancreatic cancer), and Bel-7402 (hepatoma/liver cancer) for antiproliferative activity. Of the seven compounds selected for further study five (13b, 13g, 13j, 13k and 13l) were found to give IC50values against the four cell lines comparable to those for 3. Two compounds (13f and 13i) were more active than 3 and their activity against HepG2 and MCF-7 (IC50:0.01–0.07?μM) approached that of the positive controls podophyllotoxin (podo) and CA-4. Most of compounds showed aqueous solubility (0.11–19.60?μg/mL at pH 7.4 and 2.0) better than 3. These promising results warrant further development of new compounds 13f and 13i as potential potent antitumor drug candidates.

CAN-mediated oxidation of electron-deficient aryl and heteroaryl hydrazines and hydrazides

Aryl and heteroaryl hydrazines and hydrazides were successfully oxidised using CAN, deriving dehydrazinated products. The reaction pathway strongly depends on the nature of the substrate, resulting in the formation of hydrocarbons or alkoxy derivatives. When deuterated solvents such as methanol-d4 or acetonitrile-d3 were used, a regiospecific incorporation of deuterium was achieved. Georg Thieme Verlag Stuttgart.

Aromatic allylation via diazotization: Metal-free C-C bond formation

A new method for the synthesis of allyl aromatic compounds not involving any metal-containing reagent or catalyst has been developed. Arylamines substituted with a large number of different substituents were converted via diazotizative deamination with tert-butyl nitrite in allyl bromide and acetonitrile to the corresponding allyl aromatic compounds. The allylation reaction was found to be suitable for larger scale synthesis due to short reaction times, a nonextractive workup, and robustness toward moisture, air, and type of solvent.

1-Aryl-3,3-dialkyltriazenes: A convenient synthesis from dry arenediazonium o-benzenedisulfonimides - A high yield break down to the starting dry salts and efficient conversions to aryl iodides, bromides and chlorides

This research comprises three parts. The first part regards the synthesis of 1-aryl-3,3-dialkyltriazenes 3 by reaction of dry arenediazonium o-benzenedisulfonimides 1, also coming from weakly basic aromatic amines with dimethylamine or diethylamine in aqueous solution at 0-5 °C. Yields were usually greater than 90% and there was the possibility of recovering the o-benzenedisulfonimide (5), which could be reused to prepare the salts 1. In the second part it was demonstrated that there is the possibility of reconverting the triazenes 3 into the starting stable dry salts 1 by using 5 as acid. The reactions were carried out in glacial acetic acid at 50-55 °C and normally afforded salts 1 in yields of around 90-99%. The third part concerns the setting up of two procedures for the conversion of 3 to aryl iodides 9, bromides 10 and chlorides 11. Procedure A used the corresponding aqueous hydrogen halides in acetonitrile at r.t. or 60 °C, sometimes in the presence of aqueous HBF4, sometimes Cu powder (25 examples, yields 65%-88%). Procedure B usually used anhydrous methanesulfonic acid and tetraalkylammonium halides in anhydrous acetonitrile at temperatures varying from r.t. to 80 °C, sometimes in the presence of Cu (16 examples, yields 65-88%).

Regioselective nitration of arylboronic acids

A convenient and simple regioselective ipso-nitration of arylboronic acids to nitroarenes has been developed. Under certain conditions even dinitro products were isolated.

Halodediazoniations of dry arenediazonium o-benzenedisulfonimides in the presence or absence of an electron transfer catalyst. Easy general procedures to prepare aryl chlorides, bromides, and iodides

The paper reports the results of a wide study aimed at preparing aryl chlorides 3 (19 examples), bromides 4 (19 examples), and iodides 5 (9 examples) by halodediazoniation of dry arenediazonium o-benzenedisulfonimides 1 with tetraalkylammonium halides 2. The reactions were carried out in anhydrous acetonitrile at room temperature (~20 °C) in the presence of copper powder and at 60 °C or room temperature without the catalyst. In optimal conditions the yields were from good to excellent (60 reactions, 61- 94% yield), with only a few exceptions (8 reactions, 51-55% yield). A good amount of the o-benzenedisulfonimide (7) was always recovered from the reactions and could then be reused to prepare salts 1. An interesting aspect of this research is the surprising role of the anion of o- benzenedisulfonimide (9) as an electron transfer agent.

UNUSUAL REACTION OF NITROSO COMPOUNDS WITH THE BIS(AMINOOXY)METHANE/DIBROMOISOCYANURATE SYSTEM

The reaction of nitroso compounds with bis(aminooxy)methane in the presence of dibromoisocyanurate gives the products of the formal replacement of the nitroso group by bromine.