584-48-5

Basic information

• Product Name: 1-BROMO-2,4-DINITROBENZENE
• Synonyms: 1，3-Dinitro-4-bromobenzene;1-BROMO-2,4-DINITROBENZENE;1-bromo-2,4-dinitro-benzen;2,4-dinitrophenylbromide;4-Bromo-1,3-dinitrobenzene;Benzene, 1-bromo-2,4-dinitro-;Benzene,1-bromo-2,4-dinitro-;o,p-dinitrophenylbromide
• CAS NO: 584-48-5
• Molecular Formula: C6H3BrN2O4
• Molecular Weight: 247
• EINECS: 209-539-8
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 584-48-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 71-73 °C(lit.)
• Boiling Point: 288℃
• Flash Point: 128℃
• Appearance: /
• Density: 1.910
• Vapor Pressure: 0.00406mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Water Solubility: Soluble in water (partly miscible).
• CAS DataBase Reference: 1-BROMO-2,4-DINITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2,4-DINITROBENZENE(584-48-5)
• EPA Substance Registry System: 1-BROMO-2,4-DINITROBENZENE(584-48-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36-36/37
• RIDADR: UN3459
• WGK Germany: 3
• RTECS: CY9021500
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 584-48-5(Hazardous Substances Data)

Usage

Description

1-Bromo-2,4-dinitrobenzene is an organic compound that consists of a benzene ring with a bromine atom at the 1-position and two nitro groups at the 2 and 4 positions. It is a versatile chemical intermediate used in various chemical reactions and applications.

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 
• 42996-92-9 2,4-dinitronitrosobenzene 
• 32578-27-1 2,4-dinitrophenyl trifluoromethanesulfonate 
• 5467-74-3 4-Bromophenylboronic acid 
• 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 
• 401631-88-7 C₈H₉N₅O₄ 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 

Downstream Products

• 113342-96-4 1-(2,4-dinitro-phenyl)-2,5-dihydro-pyrrole 
• 34814-24-9 Zincke salt 
• 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 
• 1594-56-5 2,4-dinitro-phenyl thiocyanate 
• 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 

Relevant articles and documents

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.

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.

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.