3460-20-6

Usage

Appearance

Yellow crystalline solid

Odor

Strong

Usage

Intermediate in the production of dyes, pharmaceuticals, and other organic compounds

Toxicity

Toxic if ingested

Irritation

Can cause irritation to the skin, eyes, and respiratory system

Environmental impact

Harmful to aquatic life

Natural occurrence

Not found naturally in the environment

Production method

Mainly produced through synthetic chemical processes

Handling and disposal

Should be handled and disposed of with care

Upstream product

• 608-21-9 1,2,3-tribromobenzene 
• 827-94-1 2,6-dibromo-4-nitroaniline 
• 100-01-6 4-nitro-aniline 
• 108-36-1 1,3-dibromobenzene 
• 610-38-8 4-bromo-1,2-dinitrobenzene 
• 51686-78-3 2,4-dibromonitrobenzene 
• 5228-61-5 5-bromo-2-nitroaniline 
• 7787-70-4 copper(I) bromide 
• 401631-97-8 C₁₀H₁₂Br₂N₄O₂ 

Downstream Products

• 31106-74-8 1,3-dibromo-2-methoxy-5-nitrobenzene 
• 99-28-5 2,6-dibromo-4-nitrophenol 
• 827-94-1 2,6-dibromo-4-nitroaniline 
• 609-16-5 3,4,5-tribromoaniline 
• 130862-75-8 bis-(4-ethoxy-3,5-dibromo-phenyl)-diazene-N-oxide 
• 60962-96-1 1,3-Dibromo-2-(4-methanesulfonyl-phenoxy)-5-nitro-benzene 
• 61038-03-7 1,3-Dibromo-2-(4-bromo-3-chloro-phenoxy)-5-nitro-benzene 
• 58291-78-4 1,3-Dibromo-2-(3-chloro-5-methyl-phenoxy)-5-nitro-benzene 
• 58291-74-0 1,3-Dibromo-2-(4-chloro-phenoxy)-5-nitro-benzene 
• 60962-93-8 1-(2,6-dibromo-4-nitro-phenoxy)-4-methoxy-benzene 
• 58291-57-9 1,3-Dibromo-2-(4-chloro-phenylsulfanyl)-5-nitro-benzene 
• 24402-71-9 2,6-Dibrom-N,N-dimethyl-4-nitro-anilin 
• 41727-70-2 3,5-dibromo-4-methoxyaniline 
• 52765-17-0 4-ethoxy-3,5-dibromo-aniline 

Relevant academic research and scientific papers

Computational and Experimental Evidence of Emergent Equilibrium Isotope Effects in Anion Receptor Complexes

The measurement of a deuterium equilibrium isotope effect (EIE) for the aryl CH···Cl- interaction of anion receptor 1H/1D is reported. Computations corroborate the results of solution measurements for a small, normal EIE in the full complex (KaH/KaD = 1.019 ± 0.010). Interestingly, isotope effects involving fragments of the anion receptor (urea, aryl ring, etc.) are predicted to produce an inverse effect. This points to an unusual and subtle structural organization effect of the anion receptor complex that changes the nature of the combined interactions to a normal isotope effect. The reversal of EIE values suggests that overall architecture of the anion receptor can dramatically impact the nature of bonding in these complexes.

Polyphenylbenzene as a platform for deep-blue OLEDs: Aggregation enhanced emission and high external quantum efficiency of 3.98%

Great efforts have been devoted to seek novel approaches for the construction of efficient deep-blue fluorescent materials, one of the most important prerequisites for the commercialization of OLEDs. Here, we report a new way to utilize polyphenylbenzene as a platform to yield a series of efficient deep-blue emitters. Nondoped multilayer electroluminescence (EL) devices using these new luminogens as emitting layers are fabricated. Maximum current efficiency (CE) of 2.0 cd A-1 is achieved and the Commission Internationale de lclairage (CIE) coordinates can stay at (0.15, 0.08), close to the saturated deep-blue (0.14, 0.08). Through rational design of the device structure, blue-violet emission with the CIE coordinates of (0.15, 0.06) can be realized. Furthermore, 10-based doped devices show deep-blue emission with improved CE as high as 4.51 cd A-1, and the external quantum efficiency (EQE) of 3.98%, which are among the best EL performance for deep-blue emission.

A Strategy towards the Multigram Synthesis of Uncommon Hexaarylbenzenes

A novel rational synthetic pathway - the "functionalization of para-nitroaniline" (FpNA) - provides substituted hexaarylbenzenes (HABs) with uncommon symmetries that bear up to five different substituents, fully avoiding regioisomeric product distributions during the reactions. 4-Nitroaniline is functionalized by a cascade of electrophilic halogenations, Sandmeyer brominations, and Suzuki cross-coupling reactions, leading to 26 substitution geometries, of which 18 structures are not available by the current established techniques. Furthermore, we demonstrate that this method is applicable to the bulk production of such systems on a multigram scale. Regarding optoelectronic properties, we demonstrate how highly functionalized HABs can show strong luminescent behavior, making these molecules very attractive to organic electronic devices.

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%).

Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase

Disclosed are substituted bis(4-aminophenyl-sulfonees of general formula STR1 wherein R1 is hydrogen, alkyl or cycloalkyl; group, R2 is hydrogen or C1 -C3 alkyl, R3 is nitrile, C1 -C3 alkylaminocarbonyl, di C1 -C3 alkylaminocarbonyl, C3 -C7 N-cycloalkyl-C1 -C3 alkylaminocarbonyl C1 -C3 alkylamino, C1 -C3, di alkylaminocarbonyl alkoxy, alkylaminosulfonyl, di C1 -C3 alkylaminono, diC1 -C3 alkylaminosulfonyl, hydroxy C1 -C3 alkyl, C1 -C3 alkylcarbonyl, amino C1 -C3 alkyl or C1 -C3 alkoxy C1 -C3 alkyl group or, when R1 and R2 are each hydrogen, R3 can be hydroxy, hydroxycarbonyl C1 -C3 alkoxy or di C1 -C3 aminocarbonylalkoxy; or, when R1 is C1 -C3 alkyl or C1 -C3 cycloalkyl and R2 is hydrogen or C1 -C3 alkyl, R3 can also be halogen, trifluoromethyl, nitro, amino, aminosulfonyl, aminocarbonyl, C1 -C3 alkylo, carboxy or C1 -C3 akoxycarbonyl; and R4 is hydrogen or, when R1 and R2 are each hydrogen and R3 is halogen or hydroxy, R4 can also be halogen, hydroxy or C1 -C3 alkoxy; or a nontoxic, pharmaceutically acceptable salt thereof. Also disclosed are pharmaceutical compositions comprising such compounds alone and in combination with dihydrofolic acid-reductage inhibitors. The compounds and compositions are useful for their inhibiting effect on bacteria, mycobacteria and plasmodia.

Substituted bis-(4-aminophenyl)-sulfones

Disclosed are substituted bis(4-aminophenyl)-sulfones of general formula STR1 wherein R1 is hydrogen, alkyl or cycloalkyl; group, R2 is hydrogen or C1 -C3 alkyl, R3 is nitrile, C1 -C3 alkylaminocarbonyl, di C1 -C3 alkylaminocarbonyl, C3 -C7 N-cycloalkyl-C1 -C3 alkylaminocarbonyl C1 -C3 alkylamino, C1 -C3, di alkylaminocarbonyl alkoxy, alkylaminosulfonyl, di C1 -C3 alkylaminono, diC1 -C3 alkylaminosulfonyl, hydroxy C1 -C3 alkyl, C1 -C3 alkylcarbonyl, amino C1 -C3 alkyl or C1 -C3 alkoxy C1 -C3 alkyl group or, when R1 and R2 are each hydrogen, R3 can be hydroxy, hydroxycarbonyl C1 -C3 alkoxy or di C1 -C3 aminocarbonylalkoxy; or, when R1 is C1 -C3 alkyl or C1 -C3 cycloalkyl and R2 is hydrogen or C1 -C3 alkyl, R3 can also be halogen, trifluoromethyl, nitro, amino, aminosulfonyl, aminocarbonyl, C1 -C3 alkyl, carboxy or C1 -C3 alkoxycarbonyl; and R4 is hydrogen or, when R1 and R2 are each hydrogen and R3 is halogen or hydroxy, R4 can also be halogen, hydroxy or C1 -C3 alkoxy; or a nontoxic, pharmaceutically acceptable salt thereof. Also disclosed are pharmaceutical compositions comprising such compounds alone and in combination with dihydrofolic acid-reductase inhibitors. The compounds and compositions are useful for their inhibiting effect on bacteria, mycobacteria and plasmodia.

Alkyl Nitrite-Metal Halide Deamination Reactions. 7. Synthetic Coupling of Electrophilic Bromination with Substitutive Deamination for Selective Synthesis of Multiply Brominated Aromatic Compounds from Arylamines

Aromatic amines undergo substitution with copper(II)bromide that is in competition with substitutive deamination when these reactions are performed with tert-butyl nitrite.Except for the exceptionally reactive 4-substituted 1-aminonaphthalenes,which undergo selective bromine substitution at the 1- and 2-positions in relatively high isolated yields,rates for oxidative bromination and substitutive deamination are not sufficiently different that selective multiple bromination can be achieved.Oxidative bromination of N,N-dimethylaniline by copper(II)bromide occurs with partial dealkylation,and nitration products are observed from reactions performed with copper(II)bromide and tert-butyl nitrite.Implications of these results for the successful utilization of copper(II)bromide/tert-butyl nitrite combinations in substitutive deamination reactions of aromatic amines are discussed.Multiply brominated aromatic compounds are produced from aromatic amines in high yield through treatment of the aromatic amine with the combination of molecular bromine and catalytic quantities of copper(II)bromide and,following a normally brief time delay,with tert-butyl nitrite.All unsubstituted aromatic ring positions ortho and para to the amino group,as well as the position of the amino group,are substituted by bromine.The only observed byproducts from use of this procedure (usually 2percent yield) are the partially brominated benzene derivatives.