13073-25-1

Basic information

• Product Name: 2-Bromo-6-nitrophenol
• Synonyms: TIMTEC-BB SBB008567;2-BROMO-6-NITROPHENOL;6-NITRO-2-BROMOPHENOL;2-Bromo-6-nitropheno;3-Bromo-2-hydroxynitrobenzene;Phenol, 2-broMo-6-nitro-;6-BroMo-2-nitrophenol;2-BroMo-6-nitrophenol, 97+%
• CAS NO: 13073-25-1
• Molecular Formula: C₆H₄BrNO₃
• Molecular Weight: 218
• EINECS: 1308068-626-2
• Product Categories: Fluorobenzene;Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 13073-25-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 66-70 °C(lit.)
• Boiling Point: 227.2 °C at 760 mmHg
• Flash Point: 91.2 °C
• Appearance: /
• Density: 1.881 g/cm³
• Vapor Pressure: 0.052mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: Room temperature.
• Solubility: Chloroform; Methanol
• PKA: 5.36±0.24(Predicted)
• CAS DataBase Reference: 2-Bromo-6-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-6-nitrophenol(13073-25-1)
• EPA Substance Registry System: 2-Bromo-6-nitrophenol(13073-25-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36/37-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13073-25-1(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

2-Bromo-6-nitrophenol is an intermediate used in the synthesis of N-Hydroxy Eltrombopag (H825795), which is a derivative compound of Eltrombopag (508000), an agonist of the Thrombopoietin (Tpo) receptor, used as treatment for thrombocytopenia.

InChI:InChI=1/C6H4BrNO3/c7-4-2-1-3-5(6(4)9)8(10)11/h1-3,9H

Upstream product

• 95-56-7 2-hydroxybromobenzene 
• 64-19-7 acetic acid 
• 88-75-5 2-hydroxynitrobenzene 
• 110-89-4 piperidine 
• 98775-19-0 2-bromo-6-nitrophenyl methyl ether 
• 585-79-5 m-nitrobromobenzene 
• 7726-95-6 bromine 
• 95-55-6 2-amino-phenol 
• 100782-02-3 2-bromo-6-nitrophenol t-butylamine salt 
• 577-19-5 2-nitrophenyl bromide 

Downstream Products

• 15969-09-2 2,4-dibromo-6-nitrophenol 
• 2316-50-9 2-bromo-4,6-dinitrophenol 
• 28165-50-6 2-amino-6-bromophenol 
• 688363-73-7 8-bromo-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 853642-87-2 8-bromo-4-(2-fluoro-benzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine 
• 853642-88-3 4-[4-(2-fluoro-benzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl]-piperazine-1-carboxylic acid tert-butyl ester 
• 116557-46-1 3-bromo-2-methoxyphenylamine 
• 860584-68-5 2-bromo-6-iodoanisole 
• 55229-71-5 acetic acid-(2-bromo-4,6-dinitro-phenyl ester) 
• 98775-19-0 2-bromo-6-nitrophenyl methyl ether 
• 688363-79-3 1-bromo-3-nitro-2-[(phenylmethyl)oxy]benzene 
• 1013643-09-8 7-bromobenzo[d]oxazole-2(3H)-thione 
• 1263412-98-1 2,2-difluoro-4-[(3-fluorophenyl)methyl]-8-(1-hydroxyethyl)-2H-1,4-benzoxazin-3(4H)-one 
• 1263413-10-0 3-{[2,2-difluoro-8-[(1S)-1-hydroxyethyl]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl]methyl}benzonitrile 

Relevant articles and documents

Selective nitration of phenols using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid under aprotic conditions

A mild, efficient and regioselective method for the mononitration of phenolic compounds is described using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid in CH2Cl2 at room temperature.

Light-Controlled Tyrosine Nitration of Proteins

Tyrosine nitration of proteins is one of the most important oxidative post-translational modifications in vivo. A major obstacle for its biochemical and physiological studies is the lack of efficient and chemoselective protein tyrosine nitration reagents. Herein, we report a generalizable strategy for light-controlled protein tyrosine nitration by employing biocompatible dinitroimidazole reagents. Upon 390 nm irradiation, dinitroimidazoles efficiently convert tyrosine residues into 3-nitrotyrosine residues in peptides and proteins with fast kinetics and high chemoselectivity under neutral aqueous buffer conditions. The incorporation of 3-nitrotyrosine residues enhances the thermostability of lasso peptide natural products and endows murine tumor necrosis factor-α with strong immunogenicity to break self-tolerance. The light-controlled time resolution of this method allows the investigation of the impact of tyrosine nitration on the self-assembly behavior of α-synuclein.

Novel method for preparing Eltrombopag intermediate

The invention provides a method for preparing a compound shown as the formula I (please see the formula in the description). The method specifically comprises the following steps that 1, a compound shown as the formula (II) (please see the formula in the description) reacts with a compound shown as formula (V) (please see the formula in the description) under the alkaline condition to generate a compound shown as the formula (III) (please see the formula in the description); 2, the compound shown as the formula (III) (please see the formula in the description) reacts with a compound shown as the formula (VI) (please see the formula in the description) under the alkaline condition in the presence of palladium carbon to generate a compound shown as the formula (IV) (please see the formula in the description); 3, the compound shown as the formula (IV) (please see the formula in the description) reacts in the presence of palladium carbon and a hydrogen source under the alkaline condition to generate the compound shown as the formula (I) (please see the formula in the description). According to the method, design is ingenious, protecting group removal, dechlorination and nitro reduction are together completed in the final hydrogenation process, and the purity of the obtained compound shown as the formula (I) (please see the formula in the description) is high; the most important thing is that compared with other Suzuki coupling agents, cost of palladium carbon is lower, a source of palladium carbon is wide and easy to obtain, palladium carbon can be directly recycled and reused after being simply filtered and separated, and therefore the material cost is greatly reduced; meanwhile, emission of three wastes is reduced, and the method is quite suitable for industrialized production.