3460-18-2

Basic information

• Product Name: 2,5-Dibromonitrobenzene
• Synonyms: 2,5-DIBROMONITROBENZENE;Dibromonitrobenzene;2,5-Dibromo-1-nitrobenzene;2 5-DIBROMONITROBENZENE 98% (GC);2,5-Dibromonitrobenzene,98%;2,5-DIBROMONITROBENZENE 99%;1-Nitro-2,5-dibromobenzene;2-Nitro-1,4-dibromobenzene
• CAS NO: 3460-18-2
• Molecular Formula: C₆H₃Br₂NO₂
• Molecular Weight: 280.9
• EINECS: 222-404-8
• Product Categories: Miscellaneous;Benzene derivates;Bromine Compounds;Nitro Compounds;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;intermediate;Pyridines
• Mol File: 3460-18-2.mol

Chemical Properties

• Melting Point: 82-84 °C(lit.)
• Boiling Point: 266.4°C (rough estimate)
• Flash Point: 114.9 °C
• Appearance: Yellow/Crystalline Powder
• Density: 2.374 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0142mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water.
• BRN: 1950425
• CAS DataBase Reference: 2,5-Dibromonitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dibromonitrobenzene(3460-18-2)
• EPA Substance Registry System: 2,5-Dibromonitrobenzene(3460-18-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-50-20/21/22
• Safety Statements: 26-60-61-36/37/39-22
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• HazardClass: 9
• Hazardous Substances Data: 3460-18-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

2,5-Dibromonitrobenzene is a halogen-substituted nitrobenzenes used against Tetrahymena pyriformis due to its inhibitory and toxicity activities.

Purification Methods

It crystallises from Me2CO or EtOH. [Beilstein 5 H 250, 5 II 190, 5 III 621, 5 IV 732.]

InChI:InChI=1/C6H3Br2NO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H

Upstream product

• 106-37-6 1.4-dibromobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 98-95-3 nitrobenzene 
• 99277-71-1 4-bromo-2-nitrobenzoic acid 
• 106-40-1 4-bromo-aniline 
• 7697-37-2 nitric acid 
• 14938-99-9 N-<2-Nitro-phenylamino>-maleinsaereimid 

Downstream Products

• 5465-66-7 5-bromo-2-piperidin-1-yl-nitrobenzene 
• 856364-94-8 1-ethoxy-2-(4-bromo-2-nitro-phenoxy)-ethane 
• 99630-04-3 2-(4-bromo-2-nitrophenylamino)propionic acid 
• 107523-11-5 9-(4-bromo-2-nitrophenyl)carbazole 
• 116153-30-1 2,4-di-carbazol-9-yl-1-nitro-benzene 
• 857600-65-8 4-bromo-N-(4-methoxyphenyl)-2-nitro-aniline 
• 89980-83-6 2-(4-bromo-2-nitro-anilino)-ethanol 
• 154252-46-7 N-(4-bromo-2-nitro-phenyl)-N-methyl-hydrazine 
• 78627-93-7 1,4-bis(trimethylsilyl)-2-nitrobenzene 
• 107618-12-2 4-(4-Bromo-2-nitro-phenylamino)-piperidine-1-carboxylic acid ethyl ester 
• 100487-81-8 2-(4-bromo-2-nitro-phenyl)malonic acid dimethyl ester 
• 7693-52-9 4-bromo-2-nitrophenol 
• 29679-22-9 Bis-4-bromo-2-nitrophenyl-selenid 
• 63213-03-6 1,2-bis(3-bromophenyl)diazene 

Relevant articles and documents

Synthesis and: In vitro evaluation of naphthalimide-benzimidazole conjugates as potential antitumor agents

A series of novel naphthalimide-benzimidazoles was designed and synthesized for the first time and studied for their effect on antiproliferative activity. Some of these compounds possessed good antitumor activity towards the tested cancer cell lines. Noticeably, (diethylamino)ethyl 15 and (dimethylamino)ethyl 23 derivatives displayed superior antiproliferative activity towards human cancer cell lines with MG-MID GI50 values of 1.43 and 1.83 μM, respectively. Preliminary investigation revealed that compounds 15 and 23 might bind with ct-DNA through the intercalation mode which is responsible for potent bioactivity. Moreover, transportation behaviour indicated that these molecules could efficiently bind to and be carried by bovine albumin, and the hydrogen bonding and hydrophobic interactions played important roles in interaction with serum albumin.

Aromatic ring liquid crystal compound and liquid crystal composition and application thereof

The invention relates to an aromatic ring liquid crystal compound, a liquid crystal composition and an assembly suitable for a microwave region and a millimeter wave region of a high-frequency technology or an electromagnetic spectrum, and particularly a phase shifter and a microwave array antenna. The liquid crystal composition provided by the invention at least comprises a compound represented by a general formula I. The liquid crystal composition provided by the invention is good in stability, high in response speed and wide in liquid crystal phase temperature range.

Exploring the nitro group reduction in low-solubility oligo-phenylenevinylene systems: Rapid synthesis of amino derivatives

A small series of amino oligo-phenylenevinylenes (OPVs) were successfully synthesized from their nitro-analogs in a rapid, simple, and highly efficient fashion employing a sodium sulfide/pyridine system as a reducing agent. In this research, classic and sustainable reduction methodologies including NH4HCO2/Zn and a choline chloride/tin (II) chloride deep eutectic solvent (DES) were also evaluated, showing degradation products, incomplete reactivity, and product isolation difficulties in all cases. The straightforward Na2S/pyridine synthetic protocol proved to maintain the E-E stereochemistry of the OPV backbone that has been previously assembled by the Mizoroki–Heck cross-coupling reaction. Also, the optoelectronic properties were determined and discussed, considering the amino group insertion in these conjugated systems as a contribution for future construction of novel materials with applications in supramolecular electronics, light harvesting, and photocatalysis.

Preparation method of high-purity 3-bromo -9- phenyl carbazole

The invention discloses a preparation method of high-purity 3-bromine-9-phenylcarbazole, and belongs to the field of synthesis of organic chemicals. The method comprises the following steps: (1) conducting a nitratlon reaction on benzene dibromide to prepare an intermediate, that is, 1,4-dibromo-2-nitrobenzene; (2) enabling 1,4-dibromo-2-nitrobenzene and diphenylamine to have an Ullmann coupling reaction to prepare an intermediate, that is, (4-bromine-2-nitrobenzophenone) diphenylamine; (3) enabling the intermediate, that is, (4-bromine-2-nitrobenzophenone) diphenylamine to have a reduction reaction to prepare an intermediate, that is, (4-bromine-2-aminophenyl) diphenylamine; and (4) enabling the intermediate, that is, (4-bromine-2-aminophenyl) diphenylamine, to have a diazotization ring closing reaction to prepare 3-bromine-9-phenylcarbazole. 3-bromine-9-phenylcarbazole prepared through the method is used in the fields of OLED photoelectric materials, medicines, dyes, pesticides and the like, and is an important carbazole intermediate; the reaction operation is simple, the cost of the raw materials is low, the yield is relatively high, and the quality is high; and moreover, the process of removing dibromo in the traditional preparation method is avoided, and the production convenience is greatly improved.

Method for synthesizing dibromobenzene -2,5- 1,4- diiodo benzene (by machine translation)

The synthetic method disclosed by the invention comprises 1,4 - the following steps: the, synthesis method disclosed by. the, invention has a good industrial production prospect, 1,4 - in the prior, art that, the raw materials are firstly, 2,5 - subjected to a nitrification step and then subjected to 2,5 - an iodine, generation step to generate 2,5 - the second bromo,4-diiodo benzene 1,4 . (by machine translation)

Effective synthesis of benzimidazoles-imidazo[1,2-a]pyrazine conjugates: A comparative study of mono-and bis-benzimidazoles for antitumor activity

A novel series of 6-substituted-8-(1-cyclohexyl-1H-benzo[d]imidazole-6-yl)imidazo[1,2-a]pyrazine and 6-substituted-8-(1-benzyl-1H-benzo[d]imidazole-6-yl)imidazo[1,2-a]pyrazine is first time synthesized and screen in vitro biological activity for 60 human cancer cell lines representing nine different cancer types. Derivatives 10 and 36 show antitumor activity for all tested cell lines, display comparable full panel mean-graph midpoint growth inhibition (MG_MID GI50) values of 2.10 and 2.23 μM, respectively. Furthermore, these derivatives show strong binding interactions with DNA and bovine serum albumin (BSA), studied through absorption, emission, and circular dichroism techniques. These spectroscopic studies reveal that imidazo[1,2-a]pyrazine-benzimidazoles 10 and 36, intercalate with ct-DNA as a leading interaction for fundamental biologically significant effects, with monobenzimidazole show better activity than bisbenzimidazole. These experiments have confirmed that the imidazo[1,2-a]pyrazine and benzimidazole moieties are efficient pharmacophores to trigger binding to DNA. These compounds have also interacted with bovine serum albumin protein that demonstrating high values of binding constant.

Synthetic method of 2,5-dibromo-p-phenylenediamine

The invention discloses a synthetic method of 2,5-dibromo-p-phenylenediamine. According to the method, the 2,5-dibromo-p-phenylenediamine is synthesized from a compound shown as I, namely, p-dibromobenzene serving as a starting material. By adopting the synthetic method of the 2,5-dibromo-p-phenylenediamine disclosed by the invention, the 2,5-dibromo-p-phenylenediamine can be effectively synthesized. Moreover, the synthetic method has the advantages of high synthesis efficiency, safe production, simple process operation, short production period and the like, so that the method is more suitablefor large-scale and industrialized production of the 2,5-dibromo-p-phenylenediamine.

A compound 5, 8 - II (3, 4 - ethylene dioxy thienyl) - quinoline synthesis method

The invention discloses a synthetic method of 5,8-bi(3,4-ethylenedioxy thienyl)-quinoline. The method comprises the steps of with 3,4-ethylenedioxy thienyl (EDOT) and p-dibromobenzene as substrates, brominating hydrogen at the position 2 of EDOT by using N-bromosuccinimide in the presence of tetrahydrofuran and acetic acid; performing nitrification on p-dibromobenzene, and performing Skraup reaction on a product obtained through reduction to generate 5,8-dibromo quinoline; enabling a product obtained by performing Grignard reaction on brominated EDOT to react with 5,8-dibromo quinoline under the catalytic action of nickel chloride to generate 5,8-bi(3,4-EDOT)-quinoline; performing electrochemical characterization of dyeing properties of the product. The synthetic method is simple and feasible, and has industrial prospects.

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.

Donor-acceptor conjugated polymers based on thieno[3,2-b] indole (TI) and 2,1,3-benzothiadiazole (BT) for high efficiency polymer solar cells

A universal synthetic strategy toward thieno[3,2-b]indole (TI) derivatives was developed. Three conjugated polymers (PTIBT, PTITBT and PTIDTBT) containing N-alkyl-TI as the donor units, 2,1,3-benzodiathiazole (BT) as the acceptor units and thiophene as the spacers were synthesized. The thiophene spacers have a dramatic impact on the physical and electrochemical properties of these copolymers. These polymer donors were used for the fabrication of bulk heterojunction polymer solar cells (PSCs). Preliminarily, power conversion efficiencies (PCEs) based on the device structure of ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al exhibit a large distinction (1.61% for PTIBT, 5.83% for PTITBT and 1.79% for PTIDTBT) at optimal device fabrication conditions. The device based on PTITBT:PC71BM (1:3, w/w) shows the best PCE of 5.83% (Voc = 0.69 V, Jsc = 13.92 mA cm-2, FF = 61.8%), which represents one of the best performances among PCDTBT analogues. In addition, the Jsc of 13.92 mA cm-2 is also among the highest Jsc values of all PCDTBT analogues. On the basis of our results, one can conclude that incorporating TI and its derivatives into donor-acceptor conjugated polymers is a feasible and effective way to develop novel donor materials for high efficiency PSC applications.