488-48-2

Basic information

• Product Name: BROMANIL
• Synonyms: 2,3,5,6-Tetrabromo-1,4-benzoquinone;2,3,5,6-Tetrabromobenzo-1,4-quinone;2,3,5,6-tetrabromo-p-benzoquinon;2,3,5,6-Tetrabromo-p-benzoquinone;2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrabromo-;2,5-Cyclohexadiene-1,4-dione,2,3,5,6-tetrabromo-;4-dione,2,3,5,6-tetrabromo-5-cyclohexadiene-1;bromanyl
• CAS NO: 488-48-2
• Molecular Formula: C₆Br₄O₂
• Molecular Weight: 423.68
• EINECS: 207-679-4
• Product Categories: Benzoquinones;Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials;Oxidation;Synthetic Organic Chemistry;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 488-48-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 292-294 °C(lit.)
• Boiling Point: 340.5 °C at 760 mmHg
• Flash Point: 120 °C
• Appearance: Yellow/Crystalline Powder
• Density: 3.127 g/cm³
• Vapor Pressure: 8.54E-05mmHg at 25°C
• Refractive Index: 1.806
• Storage Temp.: Amber Vial, -20?C Freezer
• Solubility: Acetone (Slightly), DMSO (Slightly)
• Stability: Light Sensitive
• BRN: 1912183
• CAS DataBase Reference: BROMANIL(CAS DataBase Reference)
• NIST Chemistry Reference: BROMANIL(488-48-2)
• EPA Substance Registry System: BROMANIL(488-48-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• RTECS: DK6772500
• HazardClass: IRRITANT
• Hazardous Substances Data: 488-48-2(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

A halogenated benxoquinone that is an effective inhibitor of photosynthetic electron transport through the spinach photosystem II and the cytochrome b6/f-complex.

InChI:InChI=1/C6Br4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11

Upstream product

• 99-28-5 2,6-dibromo-4-nitrophenol 
• 100-02-7 4-nitro-phenol 
• 371-41-5 4-Fluorophenol 
• 147-82-0 2,4,6-tribromoaniline 
• 88-89-1 2,4,6-Trinitrophenol 
• 100-09-4 4-methoxybenzoic acid 
• 123-31-9 hydroquinone 
• 65-85-0 benzoic acid 
• 106-51-4 p-benzoquinone 
• 108-95-2 phenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 4056-56-8 N-(phenylsulfonyl)-1,4-benzoquinone monoimine 
• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 
• 7732-18-5 water 

Downstream Products

• 26361-18-2 2,5-dibromo-3,6-diethoxy-1,4-benzoquinone 
• 40101-03-9 2,5-dibromohydroquinone diacetate 
• 34554-51-3 2,5-dibromo-3,6-diphenoxy-[1,4]benzoquinone 
• 63404-06-8 6,7,9,10-tetrabromo-3-(2,3,5,6-tetramethyl-phenyl)-1,4-dioxa-2-aza-spiro[4.5]deca-2,6,9-trien-8-one 
• 63404-07-9 6,7,13,14-tetrabromo-3,11-bis-(2,3,5,6-tetramethyl-phenyl)-1,4,9,12-tetraoxa-2,10-diaza-dispiro[4.2.4.2]tetradeca-2,6,10,13-tetraene 
• 76699-88-2 6,13-Dibromo-10-chloro-3-ethoxy-1-nitro-benzo[5,6][1,4]thiazino[2,3-b]phenothiazine 
• 109949-79-3 2-m-Tolyl-2,3-dihydro-1H-isoindole; compound with 2,3,5,6-tetrabromo-[1,4]benzoquinone 
• 109949-75-9 2-(2-Chloro-phenyl)-2,3-dihydro-1H-isoindole; compound with 2,3,5,6-tetrabromo-[1,4]benzoquinone 
• 109949-82-8 2-(3-Methoxy-phenyl)-2,3-dihydro-1H-isoindole; compound with 2,3,5,6-tetrabromo-[1,4]benzoquinone 
• 109949-83-9 2-(4-Methoxy-phenyl)-2,3-dihydro-1H-isoindole; compound with 2,3,5,6-tetrabromo-[1,4]benzoquinone 
• 91238-37-8 1-Benzyl-1,4-dihydro-pyridine-3-carboxylic acid amide; compound with 2,3,5,6-tetrabromo-[1,4]benzoquinone 
• 117209-94-6 2-Dimethylamino-3,5,6-tribrom-1,4-benzochinon 

Relevant articles and documents

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Design, synthesis and cytotoxic activity of water-soluble quinones with dibromo-p-benzoquinone cores and amino oligo(ethylene glycol) side chains against MCF-7 breast cancer cells

A series of novel quinones was synthesized by reacting tetrabromo-p-benzoquinone with amino oligo(ethylene glycol) dendrons of generation numbers g = 0-2. According to the performed shake-flask experiments, their aqueous solubility (S = 18 mg l?1-1.6 g ml?1) and partition coefficients (log?Poct/wat = 2.53-0.21) can be tuned in a wide range as a function of g. In vitro cytotoxicity assays of tetrabromo-p-benzoquinone and its derivatives against MCF-7 human breast cancer cells showed a concentration- and generation-specific biological activity with IC50-values as low as 0.8 μM. Further investigations revealed a considerable selectivity against cancer cells, as indicated by a weak cytotoxicity against human skin fibroblast cells (>80% survival) within the studied range of concentrations. The results demonstrate that these novel amino oligo(ethylene glycol) dendrons depict versatile tools to ameliorate physical and pharmacological characteristics of extremely hydrophobic molecules and make them susceptible to biological applications.

The mediatory activity of Ce(IV)/Ce(III) redox system immobilized in nafion film on glassy carbon

Properties of the glassy carbon modified with Ce(III) ions immobilized in Nafion film and the catalytic activity of these ions or the catalytic activity of the modified conducting phase in electrochemical oxidation of some hydroquinone, phenylenediamine and 4-hydroxybenzoic acid derivatives were investigated. The redox activity was characterized in aqueous solutions of perchloric acid by cyclic voltammetry. The redox process was diffusion-limited which can suggest that the cerium(III) ions immobilized in the Nafion multilayer was rate-controlling. The increase of anodic peaks of investigated compounds during oxidation on the modified electrode (GC/Nafion/Ce(III)), and drastic decrease of cathodic peak related to Ce(IV) ions reduction, points to the mediatory activity of these ions. The increase of oxidation currents observed during preparative electrolyses indicates the catalytic properties of the modified conducting phase. The preparative electro-oxidation of investigated compounds showed that the 100% conversion of the substrate occurs in the shortest time on glassy carbon modified with Ce(III) ions immobilized in Nafion film. AFM tapping mode phase imaging was used to identify the hydrophobic and hydrophilic regions of Nafion perfluorosulfonate cation exchange membranes. The clusters agglomerates have a range of sizes from 5 to 30 nm.