609-21-2

Basic information

• Product Name: 4-AMINO-2,6-DIBROMOPHENOL
• Synonyms: 4-amino-2,6-dibromo-pheno;Phenol, 4-amino-2,6-dibromo-;TIMTEC-BB SBB006577;4-AMINO-2,6-DIBROMOPHENOL;3,5-DIBROMO-4-HYDROXYANILINE;2,6-DIBROMO-4-AMINOPHENOL;ASISCHEM U70323;4-hydroxy-3,5-dibromoaniline
• CAS NO: 609-21-2
• Molecular Formula: C₆H₅Br₂NO
• Molecular Weight: 266.92
• EINECS: 210-185-1
• Product Categories: Phenol&Thiophenol&Mercaptan;Anilines, Amides & Amines;Bromine Compounds;Phenols;Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 609-21-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 195-196 °C(lit.)
• Boiling Point: 295.6 °C at 760 mmHg
• Flash Point: 132.6 °C
• Appearance: beige to pale brown crystalline powder
• Density: 2.0444 (rough estimate)
• Vapor Pressure: 0.000858mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.17±0.23(Predicted)
• BRN: 2803732
• CAS DataBase Reference: 4-AMINO-2,6-DIBROMOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-2,6-DIBROMOPHENOL(609-21-2)
• EPA Substance Registry System: 4-AMINO-2,6-DIBROMOPHENOL(609-21-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 609-21-2(Hazardous Substances Data)

Usage

Chemical Properties

beige to pale brown crystalline powder

Synthesis

The synthesis of 4-amino-2,6-dibromophenol is as follows:4-Nitro-2,6-dibromophenol (2.97g, 10mmol) was dissolved in ethanol (15ml) and water (3ml), and acetic acid (1ml) was added. Then heat and stir to raise the temperature to 80°C, and add iron powder (1.68g, 30mmol) in batches. After the addition is complete, the reaction solution is kept warm for 30 minutes, heating is stopped, filtered while hot, the filtrate is concentrated under reduced pressure, then ethyl acetate and water are added to the concentrated residue to extract, the organic phases are combined and dried, filtered, and the solvent is removed under reduced pressure. The residue was finally separated by column chromatography (ethyl acetate/petroleum ether=1/3) to obtain 4-amino-2,6-dibromophenol (2.52g, 94.4% yield).

InChI:InChI=1/C6H5Br2NO/c7-4-1-3(9)2-5(8)6(4)10/h1-2,10H,9H2

Upstream product

• 99-28-5 2,6-dibromo-4-nitrophenol 
• 38676-25-4 4-Diazo-2,6-dibromo-2,5-cyclohexadienone 
• 619-57-8 p-hydroxybenzamide 
• 19628-79-6 2,6-dibromo-4-nitrosophenol 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 197961-56-1 2,6-dibromo-[1,4]benzoquinone-4-(4-dimethylamino-phenylimine) 
• 64-19-7 acetic acid 
• 100-02-7 4-nitro-phenol 
• 2582-33-4 2,6-dibromophenolindophenol 
• 7732-18-5 water 
• 793663-18-0 2,6-dibromo-[1,4]benzoquinone-4-oxime 
• 61841-50-7 2,6,2',6'-tetrabromo-4,4'-azo-di-phenol 
• 856345-30-7 2,6,2'-tribromo-4,4'-azo-di-phenol 

Downstream Products

• 108761-50-8 acetic acid-(4-ethoxy-3,5-dibromo-anilide) 
• 608-33-3 2,6-dibromophenol 
• 38676-25-4 4-Diazo-2,6-dibromo-2,5-cyclohexadienone 
• 537-45-1 2,6-Dibrom-1,4-benzochinon-4-chlorimin 
• 154928-49-1 2,6-dibromo-N-(2,4-dinitrophenyl)-4-aminophenol 
• 19643-45-9 2,6-dibromo-1,4-benzoquinone 
• 190844-68-9 N-(o-bromobenzylidene)-4-amino-2,6-dibromophenol 
• 107590-48-7 2,6-dibromo-4-(p-tolylimino)-1,4-benzoquinone 

Relevant articles and documents

-

-

Substituted pteridinones as p90 ribosomal S6 protein kinase (RSK) inhibitors: A structure-activity study

The activity of p90 ribosomal S6 kinase 2 (RSK2) has emerged as an attractive target for cancer therapy due to its role in the regulation of diverse cellular processes, such as cell transformation and proliferation. Several pan-RSK inhibitors have been identified with BI-D1870 and the pseudo-analogs LJH685 and LJI308 being the most selective, potent, and frequently used small molecule inhibitors. We designed and synthesized a series of pteridinones and pyrimidines to evaluate the structural features of BI-D1870 that are required for RSK2 inhibition. We have identified inhibitors of RSK2 activity, evaluated their target engagement in cells, and measured their effect on cell viability and cytotoxicity in the MOLM-13 acute myeloid leukemia (AML) cell line. The results of our studies support that RSK2 inhibition can be achieved in MOLM-13 cells without potent cytotoxicity. The structure-activity data from this study will be used as a platform to develop novel RSK2 inhibitors.

Synthesis and some transformations of polybrominated quinone diazides

The reduction of polybrominated o- and p-nitrophenols with granular tin in concentrated aqueous HCl gave polybrominated aminophenols which were diazotized with sodium nitrite in concentrated sulfuric acid at 0°C to obtain polybrominated o- and p-quinone diazides. Their thermolysis with elimination of nitrogen generated ketocarbenes which reacted with acetylacetone to form insertion products at the activated methylene group. Ketocarbenes generated from o-quinone diazides reacted with typical dipolarophiles such as acetonitrile, benzonitrile, styrene, and phenylacetylene to afford the corresponding [3 + 2]-cycloaddition products.